Advice by Amy: Pretty Unapproachable



Dear Amy,

Is it possible that being attractive is more of a detriment than an asset?

So not to toot my own horn but I’ve been told that I’m attractive, gorgeous etc. I’m also outgoing, independent and a genuine person that just wants to be happy with a man that treats her well. I don’t even like overly attractive guys, they are too high maintenance! Having that said, I also always have to be the one that makes a move on a guy, or else it just never happens.

I have a friend from high school, we got drunk one night and I told him I used to have a huge crush on him. His response totally blew my mind. He said he also liked me and that he just thought I was “out of his league”. FYI, I lost all interest when he dated my friend back in the day, I don’t like him that way anymore. His response made me think of all the guys I liked, and how I always had to be the one doing the “chasing”, at least until they got the point.. Like “Hey, I like you, I would love to date you and do things to you” you know?!

I get approached by guys, don’t get me wrong, but it’s always the douchebag that really is aiming high if you know what I mean. It’s never the nice guy, or the smart guy, or at least the rich guy. It’s the asshole that tries to get with me. The one that just wants to hook up. Did I mention I’m not the hook up type?

This problem might seem like not a bad problem to have to some people but think about it, if you’re always the one doing the work… If you are deemed unapproachable based on your looks… then where is the fun in that? It doesn’t help that I’m a romantic at heart but I’ve seen it with other girls, they get swept off their feet and here I am, pining over the guys I like.

Pretty Unapproachable

Dear Pretty Unapproachable,

When I was going to university and at home for a visit, I ran into one of the guys I graduated with. He told me about this girl in one of his classes, and he called her his “attainable girl”. I don’t know if he had even talked to her at this point, but his labeling of her was based solely on her looks. Pretty, but not too pretty. She was within the imaginary parameters of what he thought a guy like him could have. And he was average. So that’s where he set his sights.

It sounds like the kind of men you like are generally intimidated by you. And that’s it’s not just your looks that do it. In the instance with your friend from high school. You call him a friend, so obviously he knows you as a person and not just some hottie he saw in the hallways every day. So he knows that you’re an independent, outgoing, and genuine person. And that combination with your looks is probably what he thought put you out of his league. Don’t change. I know it’s frustrating to not get the things you want right now, or to have to always be the one to put in so much work for so little reward. But someone who considers you out of their league and makes a move anyways is exactly the kind of person you want to be with. That person has ambition and confidence. However, depending on where you look, you’re not going to find a bunch of men like this. They aren’t exactly a dime a dozen at the clubs on the weekend, you know?

As far as the men who do approach you goes: Confident men will approach any woman they are attracted to, regardless of how hot the rest of us think she is or isn’t. Not because they think every woman is a sure thing for them, but because they know it’s a definite no if they don’t at least take the shot. Confident men get nervous and intimidated too, but they say hi to you anyways and hope you smile and say hi back. Arrogant men will disregard any woman who doesn’t meet their physical standards and expect those they “choose” will fall at their feet. And most of their attraction to you will be based on other people’s perception of how “hot” their arm candy is.

Unfortunately, I don’t have an easy answer for you. If the type of man you’re looking for is the one who needs a little encouragement, you’re going to have to give it to him. The average nice guy probably isn’t going to come up and say hi if you haven’t at least already made eye contact and given him a smile. Or said hi first. When I take my dog to the dog park, he ignores a lot of the other dogs. But when he meets one he likes, he’s like, “hey, did you see me? No?”, then jumps up and humps it until it turns around and chases him in circles and he runs around, tongue hanging out, so happy. Ok, so not the perfect analogy, but you get what I mean! You may have to be the one to break the ice most of the time, but that doesn’t mean you have to settle for a guy who expects you to take the lead all the time. You can either keep on keeping on the way you have been, or you can make some adjustments to your dating life to try and encourage someone to pursue you. Try online dating with private pictures. You’ll have to sift through some profiles and put some time into conversations, but you could meet someone great. Plus, with online dating, it’s a lot less intimidating for men to pursue a beautiful woman. Ask friends to set you up. Smile at the cute guy at the coffee shop. Go for lunch at the cafeteria at the same time as that cute, nerdy guy in your office. Sit next to the sexy, smart guy in your Wednesday class and ask him how his assignment is coming along. Put the vibes out and see what comes back.

Romance doesn’t always come to us the way we expect. You may not meet a guy who is going to sweep you off your feet with a great line or a huge romantic gesture in order to get your attention. But maybe you’ll meet a guy who feels lucky that a woman like yourself was interested in a guy like him and he’ll take time every day that you’re together showing you how much he values you and appreciates that moment you first said hi.

(Also, you said this in your letter: “I don’t even like overly attractive guys, they are too high maintenance!” What makes you think that men think any differently when they look at you? Hi pot, this is kettle. Stereotypically speaking, they’re probably thinking that not only are you out of their league, but that even if you were interested in them, you’re probably high maintenance.)



How often do you get asked about your “number”? You know, the number of penises or vaginas that have met with your corresponding parts. I have found myself being asked this question a few times over the years, and as recently as the last couple of weeks. I tried to figure it out a year or so ago. I made a list which had entries like: Mike, Jon, Keith, guy I met at the pump that night, guy who was on acid while I was on E at Sasquatch, etc. After I wrote down what I thought was all of them, I counted them up and was at a number that I thought was rather reasonable given my age and dating lifestyle. I was a virgin until I was 22. No, 23. Wait. 22. Anyways. I waited. Not for anything specific. I wasn’t waiting for “the one”. I was just waiting. I like to do things in my own time and that was the time for me. His name was Mike and he slept on a futon. It wasn’t good, and it wasn’t a big deal. It just…was. I didn’t even tell any of my friends about it at the time because that was how boring and matter-of-fact it was. Well, that’s done. *brushes off hands*

So, back to the numbers. I was at a number that some of you would probably consider high, but I’ve been having sex for 12 years with no long-term relationship in there. And I like to drink, and I like to have sex. It’s a winning combination. So I thought it was rather reasonable. But then I started remembering more. I’d be driving in my car and another one would pop into my head. And then another. And another. Months down the road, I was still remembering men I’d forgotten. (Sorry fellas! Be more memorable next time!) So I decided to stop keeping track.

I started talking to this guy on Tinder. It started out well enough. We exchanged phone numbers and started texting. He’s younger than me, 27, and he lives a couple of hours away. He wanted to play 20 questions and asked if there was anything off limits. I told him he could ask me anything he wanted and if I felt like it was too far, I just wouldn’t answer it. The first half of the questions were basics…favourite food, where we want to travel, etc. And then of course there was the measurements question. What is it with you men and your need to know exactly how big a woman’s breasts are? Aren’t you supposed to be visual creatures? I have pictures on my profile. But that’s not good enough. And the reason is always the same…”I’m a numbers guy.” Whatever. If I’m in a good mood, I’ll tell you. Especially since I know you don’t really understand how bra sizing works and the relation between cup and band size, and anything over a 36C is going to blow your mind.

So then the questions lead into more sex talk, favourite position, weirdest place you’ve done it, and then anal. That’s where I stopped him. Not because I’m uncomfortable talking about it, but because sex is one of those topics that I don’t think should go too far when you’ve only just started to get to know each other. A good number of men will push these limits. He was fine with stopping though, and went back to regular questions.

Some days later, I found out he was married for a couple of years, they split a couple of years ago, and he hasn’t had sex since they split. First I asked him why they divorced and he said it was because she thought it was ok to sleep with other men. I told him I was sorry that happened to him and asked if she gave him a reason for why she cheated. His response was, “I dunno. Cause she’s a whore?” I guess he’s still a little bitter about it. And then I asked him why he hasn’t had sex in so long. He hasn’t met anyone special and he’s never had a one-night stand. He asked if I’ve ever had one. Uhh….yes. Have I had a lot of them? …..uhh…. I told him I’ve had a couple. Ok, you can all stop laughing now. Next, he asked how many people I’ve slept with. I laughed and said that was none of his business, and asked if a big number would bother him. He said it depends how big the number is. I asked why it would bother him. He said he didn’t know, and that maybe it wouldn’t. I said it wouldn’t matter to me, 1 or 100, I don’t care. To which he replied that he’s only had sex with 3 women, so…

When he didn’t text me the next day, I thought I had scared him off, but he messaged the day after that and regularly for the next few days after. Unfortunately, he’s terribly boring over text and can’t seem to carry on a conversation beyond the few topics we’d already discussed. Meh. I already had the feeling that this guy has some stuff to work through. And like so many other men on Tinder and Pof, he wanted to talk about sex and push the boundaries of what is acceptable conversation, but if I have a colourful, bountiful past, that could be a problem? Come on! I haven’t been guarding my sexuality all this time just waiting for you to come along like some kind of goddamn Christopher Columbus!

I feel like numbers aren’t something that we (especially women) should have to hide, and yet, we all know that if you’ve surpassed single digits in the number of partners you’ve had, you’re going to either lie about the number, or just not admit to a number at all. It’s nothing to be ashamed of, whether it’s 1 or 5 or 35, or 100, or if you’re not even on the board yet. Shout it loud and proud, if you want! But be prepared for the judgement. I would never want anyone who would judge me on it anyways, but I also don’t want to deal with having it thrown in my face like it’s a bad thing. And so my number will remain a mystery. I’m going to keep living like an Agatha Christie novel and loving who I want to love with my honey pot, and you should too.

Advice by Amy: Impatient

Dear Amy,
I started doing the online dating thing a few months ago and recently “met” a really great guy. After a few conversations, we exchanged phone numbers. We’ve been texting and it’s been going really good. We have great conversations, but just over text. We haven’t talked on the phone. He has told me several times that he is interested in finding a relationship. We talk about how our days were, and we tell each other our hopes and plans for the future. We’ve even done a bit of sexting and exchanged some sexy (but not naked) pictures. Except, we haven’t met yet. Every time we make plans, he backs out at the last minute. It’s been about a month since we started texting and I’m starting to wonder if he’s actually serious about wanting a relationship. And honestly, I now kinda feel a little embarrassed about the pictures I sent him. I really like him, but how can I tell if he’s serious?




Dear Impatient,

Isn’t waiting for a date the worst?! I have been in this same situation and I know exactly how frustrating it can be. It’s surprising and weird when you feel a connection with someone you’ve never met, but not unusual.

I think you already know the answer to your question. If he keeps backing out, and has let a month go by without meeting you, his interest is low. He may even believe that he wants a relationship, but something is holding him back, and it’s not up to you to try and fix him, or convince him. Whether it’s intentional or not, he’s leading you on. He can make all the excuses he wants, and you’ve probably accepted his excuses and made some of your own based on things he’s told you about himself. But these are just that: excuses. Even if you did meet now, what about his behaviour makes you think that you would be a priority in this man’s life?

If you’re still texting this man, you need to stop. Right now. You need to be free to focus on finding a man who wants a relationship and will put in the effort to have one with you. Now, you will likely have that little glimmer of hope in the back of your mind at this point that saying this to him will kick his ass into gear. It won’t. And his response to you will be extremely unsatisfying. He will likely give you a one word answer, or he won’t say anything at all. Both will drive you crazy and you’ll want to send him more messages. Do not do this. This is the perfect time to decide what you want and don’t want, and what you are willing to put up with in your dating life. Have a cry, let it go, and delete his number.

Online dating can be a little bit like dating on a reality TV show like The Bachelor. It’s dating in a fantasy world called Your Head. If you’ve met online dates in the past, you already know that your attraction to someone can change in an instant when you spend some one on one time with them. Take this experience and make it a personal rule to not go longer than 1-2 weeks without meeting someone you’ve met online. This should also apply to anyone you meet at the grocery store or the bar or wherever. If a date hasn’t happened within that time, move on. 2 weeks MAXIMUM. Anything beyond that and you’re allowing yourself to get invested in an illusion.

As for sending sexy pictures, just be mindful of what you send, and never feel that you HAVE to send pictures to keep a man’s interest. Pictures should be on your terms only. And only send pictures that you feel comfortable posing for, make you feel sexy, and wouldn’t die if someone else saw them. It sounds like the pictures you sent were tasteful, so don’t be embarrassed. You can ask him to delete them, and hope that he does. And if he doesn’t, well, then he’s the one holding onto the fantasy.

New Advice Section

I have an opinion on almost everything. And if you have a problem you’re not sure how to handle, I’d love to offer my opinion to you. Problem with your significant other? Not sure how to proceed with the guy from Pof who won’t ask you out? Having trouble having an orgasm? Is your friend marrying the wrong person and you don’t know how to talk to him/her about it? Do you have a strange rash in a delicate spot? It can be anything, not necessary sex or dating related. Send me your situations and questions @ and I will feature them on my blog. You can remain anonymous.


For the past few months, I have been getting requests for the pleasure of my company from several men from my past. If I were a hooker, I’d have a decent sized group of regulars. These are a few of the more interesting ones. The 20 year old kid messaged me this summer, asking me for a favour. You’re probably thinking you know exactly what kind of “favour” he’d be looking for, but you’re wrong. Sort of. He asked me if I knew of anyone I could set him up with.

“Amy I have a question”
“Hey kid, what is it?” (I don’t actually call him kid, but I won’t use his name.)
“Do u know any older women who would be interested in me? I have been trying so hard, but can’t find an older woman who likes. They think cuz of my age I’m automatically immature.”
“Interesting in you in what way? Are you wanting to date someone or just fool around? And how old are you looking for? My age or 40’s or…?”
“Just fool around. Anyone over 28.”
“Hmm I’m not sure. Most of my girlfriends are looking for relationships.”
“I’m open for a relationship, I just don’t see an older woman wanting to date a 21 year old.”
“I’ll keep an eye open for you.”
“Because ur no longer interested in me, correct?”

And there it is! He needed to check and see if there’s still a chance. I told him that I’m not interested in fooling around anymore, even though he’s cute and a good lay. What I didn’t tell him was that even if I had any friends who were interested in meeting a guy that young, I’m not sure any of them would be into the same things he is, sexually speaking. I mean, this is the same kid who wanted me to pee on him every single time we talked. He also wanted to throat fuck me until I puked and put a dildo up his ass. By all means, if you are a female over the age of 28 and into some kinky shit (which may include actual shit), let me know and I’ll hook you up.

Then there’s the Farmer. Every few months I get a message from him. Sometimes it’s to ask how I’m doing and what’s new. And sometimes it’s to ask me if I want to have a threesome. If I’m not into having another girl there, he has a buddy. The one who saw me naked when I spent the night in their hotel room. Or we have a conversation like this:

“Find a girlfriend yet? Lol”
“lol Not looking for one.”
“You should! You would like it!”
“lol Why not?”
“Not interested”
“Have you tried it?”
“No, and I’m not going to.”
“lol Well that’s no fun!”
“Men are pretty fun. You should try them.”
“No, I’m good.”
Man, I bet his ex-wife is really beating herself up about letting this one get away.

Speaking of married men. Remember this guy? I haven’t seen or spoken to him for over 3 years, until he sent me a message on Pof about a month ago. He didn’t have a picture up, but after reading his profile, I was pretty sure I knew who it was. Our exchange went something like:

“Hi, I don’t know if you remember me, but we met awhile ago, and I was wondering if you’d like to meet again.”
“Hmm, you’ll have to tell me a bit about yourself first to see if I remember you.”
“I’m from Saskatoon, we met up a couple of times and had some fun.”
“You’ll have to be more specific.” hahaha
“I guess I’m not that memorable.”
“Were you married?” (His profile now says separated.)
“Ok, I remember you.”
“Great! So would you want to meet up again? I would love to see you, I had a great time the last time.”
“No thanks. I’m not looking for anything casual.”
“Oh, ok. Well, if you change your mind…”
“Good luck.”

A week later, he messaged me again, and once again asked if I’d like to have some “fun” with him. I don’t know about you, but nowhere in my idea of fun is there included a dirty eyebrow wiggle that happens while a man is thrusting his dick inside me. Just imagine it for a moment. A guy looking down at you, obviously pretty please with himself, and wiggles his eyebrow at you. Like he’s giving you just what you want. It’s the sexual equivalent to the wink and a gun. Not sexy.

Ugh, why does my vagina have to be so magical?

And now there’s Houdini. I was sure I wrote about him previously, but I couldn’t find the post, so maybe I just thought about writing about him. We met on Pof and went on a date a couple of years ago. It was a great date! Seriously, I think we spent 6-7 hours together. We met at a pub in Cathedral for a couple of drinks and a bit to eat. Coincidentally, he took a “cab” to the pub because he didn’t want to drive after having some drinks and who was his cab driver? This guy! When he came into meet me, he was telling me about this guy who drove him and he just calls him whenever he needs a ride and this guy shows up and takes however much he wants to pay. I had used this guy years before that and turned out to be the same guy. And then of course there was that time more recently that I re-met this guy and, well, we know how that turned out. Anyways, back to our date. We got along very well, we found a lot to talk about. He’s handsome in a Sons of Anarchy kind of way, works in construction. I believe he had his own company at the time, had lived a crazy life. The kind of life where you’re not sure how someone turned out as well as they did. He left home/was kicked out when he was 14 or so. I don’t think he ever finished school, he just started working and travelling across Canada, picking up jobs as he went. So after the first pub, we went to another. It was pretty dead so we just had a drink or two and talked some more and then decided since neither of us wanted the night to end yet, we would go back to his place to watch a movie. I had just moved and didn’t even have furniture at my new place yet, so it had to be his house. I can’t even remember what movie we settled on, but I know it was bad. It had a lot of gratuitous female nudity and some animals that killed everyone after genetic mutation or something. A story as old as time. We did make out a bit, but I wouldn’t go any further with him. I called a cab to go home and he said he was hungry again and wanted to grab some food, so did I mind if he shared a ride with me part of the way. No problem. So here’s where it gets weird. We were in the north end, I live close to downtown. He gave me some money for the cab, and when we got to the lights on McCarthy and 9th, he said this is close enough for him, jumped out of the cab, and ran over to the Normanview Mall.

I literally never heard from him again. After I didn’t hear from him the next day, I texted him. No response. Maybe he didn’t get it. So I messaged him on Pof. No response, and a couple of days after that, his profile was gone. Uh, ok? That was weird.

Then a few weeks ago, I get a message from him on Pof. He’s back in Regina. He said hi and said he didn’t know if I remembered him, but we went out awhile ago and he’d love to go out with me again. I said that I did remember him, and that I remembered him disappearing and never hearing from him again. He apologized for that, said something about getting a last minute job up north that he left for right away, blah blah blah. I guess he must have forgot his phone when he left? But hey, I’m all about second chances, so I kept chatting with him. He apologized again and asked if I would like to go out with him. I said I was open to that and then gave him my number to contact me sometime. Three weeks went by. Three fucking weeks! And nothing. I mean, I shouldn’t be that surprised. It took this guy 2 years after our first date to ask for a second, so I guess waiting a few weeks for a text should be no big deal, right? I didn’t contact him again, but then just last night, he messaged me again.

“Just wanted to say hi, hope you’re doing well. I like the new pics, beautiful as always, Happy Halloween.”
“Hi, thanks.”
“I work a lot, but I’d like to see you sometime if you like.”
“I sent you my number, but you never used it…”
“No excuses there. I took too long and Pof deleted it. So if you’d like, here’s my number.”

I did end up texting him and we chatted for awhile. He wants to go out sometime this week. I’m considering it. Cause I’m all about third chances. Maybe I’ll make a date and then just…disappear.

UPDATE: We had plans to go out. I didn’t hear from him the day before our date was scheduled. I didn’t hear from him on the day our date was scheduled. I texted him the day before, but there was no response. The day AFTER our date was supposed to be, I received a text from him. He apologized for not being available and said he worked 18 hours that day. But that he’d still like to get together sometime soon. I said maybe if I had time on the weekend. I haven’t heard from him since, and I don’t care.

Sex With Friends

I don’t have sex with my friends. Friends of friends, yes. Friends of friends of friends, yes. Friends of strangers, yes. Strangers, yes. Guys who wear multiple pairs of pants, yes. But never my friends. Except that one time. And then almost this time that I’m about to tell you about.

We aren’t super close friends, but we chat (flirt) once in awhile, and recently he’s been really, really flirty. One night recently, we went for supper and had a pretty good time. The conversation flowed easily, there were a lot of jokes, and we discussed a lot of topics. One of them was music. He is a fan of bands from the 90’s and 2000’s, including Seven Mary Three (this is important for later). We were out late, and had a little too much to drink. I should mention that I’ve been chatting with another guy that I’ve been feeling pretty into, but he lives out of town and we haven’t gotten to see each other much. But even so, my attention has been focused in that direction. Due to this, I had decided before I even went out that if he made a move, I was going to turn him down. But, the whiskey had other ideas. So when he asked me if I wanted to go back to his place, I said yes. I mean, he’s pretty hot and he makes me laugh. What’s a girl to do? I’m not made of stone!

We get to his place and crack a couple of beer. I have just a couple sips out of mine before he kisses me. Oh, that’s where this is going? (I said innocently) And before I knew it, we were making out on his bed. He kissed me gently and slowly ran his hands over my body. I pulled away and told him that there was someone else I was interested in, and I shouldn’t be doing this, and should go home. He told me I shouldn’t do anything that felt wrong. So I pulled him towards me and kissed him long and deep, because being bad feels so much better than being good. He told me I could spend the night if I wanted to, and that we could just sleep. I went to the bathroom to think about it. When I came out, he was under the covers. I asked him how naked he was under there, and he told me he still had his underwear on. I said ok then, pulled my dress up over my head, handed him a straw, and let him drink it in.

I crawled into bed with him, kissed him, said good night, and rolled over. He spooned up behind me and kissed my shoulder while his fingers trailed over the curves of my body, barely touching me, grazing over the peaks and valleys, sending shivers to all the right spots. I turned towards him and met his lips with mine. He put his hand in my hair and pulled my head back. I moaned and he kissed his way down my neck and up again, licking and nibbling on my ear. I could feel how hard his dick was. I begrudgingly told him to stop.

We went back to cuddling and talking. It got real comfortable, real fast. This back and forth went on for a couple of hours. We’d talk and laugh and cuddle, and then we’d make out, going a little bit farther each time. And then he said, maybe I should put on a condom, you know, just in case. I laaauuughed! And said no. We finally called it a draw and went to sleep.

The next morning, he had to get up early for work, so he showered and got ready and then realized he still had a half hour before he even had to leave. Remember how I said I wasn’t going to hook up with this man? Well, there I was, naked except for a piece of lace covering my kitty, lying in his bed looking up at him, saying, “Well, what are you going to do with all that spare time?” He jumped back into bed pretty quickly and kissed me. Close-mouthed because it’s the morning and we’re not animals. Then he got back out of bed. “These jeans are too tight,” he says. Smooooth. And since his jeans were coming off, well, his sweater might as well come off too! He crawled up between my legs and asked if we could have sex. I told him if he couldn’t get me to agree the night before when I was drunk, the chances of me saying yes while I was hungover were not good. He told me he was going to make me wet and leave then. I suppose that seems only fair. Plus, I could just go home and pull out my vibrator after he did all the legwork ;)

Now he figures he had better get dressed and be on his way. He tells me I can stay as long as I want and sleep. So I don’t move too fast. He grabs his phone and heads to the bathroom. The bathroom is located right by the bedroom, and the entire time we were together, he was a gentleman and always turned the faucet on so I wouldn’t have to listen to him pee. This time was no exception. Except that it was the exception. I hear the faucet turn on, and then I hear, “Oh Jesus, I’m sorry. Amy, I’m so sorry,” followed by the sounds of….his ass exploding. Followed by….Seven Mary Three. Followed by more ass exploding, and his desperate apologies. “I’m sorry Amy, I’m so fucking classy. Jesus.” I am DYING laughing at this point! When he finally emerges from the bathroom, he apologizes again and tears are streaming down my face at how funny this morning turned out to be.

“Why did you start playing Seven Mary Three?! That didn’t help at all!”

“I just wanted something else to help cover up the sound and that was the first song that played on my phone. I’m so embarrassed, I thought I could make it to work, and then it hit! Oh god, now every time you hear that song, you’re going to think of this moment!”

Oh man, we laughed. So. Hard. I probably won’t be able to resist him again.

The City Worker

I’ll call him “Ron”.

I met Ron through Tinder. We had a decent conversation and I gave him my number. We texted for a few days and everything was cool. He’s 41 and works for the city. We had some decent conversations, but of course he would eventually lead it towards sex. I don’t mind talking about sex, but there’s limits. He told me a lot of things he likes, and that he’s pretty kinky. I told him that I didn’t want to keep talking about sex or things that I like and don’t like because then if we end up sleeping together, there’s weird expectations and limited surprises. Plus, I just didn’t want to only talk about sex and told him he could get to know me. He agreed, and we had some more good conversations. Then Thursday came along, and I went out. He told me ahead of time that if I needed a ride, I could call him. We hadn’t met in person yet, so I said I didn’t think that was a good idea and I didn’t want to wake him up since he starts work at 6. He said he didn’t mind. What I really meant was that I would be drunk and prone to bad decisions. He didn’t mind that either.

Well, at the end of the night, after finding and wearing a random hat and dancing on some sort of table at Q nightclub, Drunk Amy remembered that there was someone who would drive us home and we didn’t need to pay for a cab. Obviously my friend thought this was a great idea, especially since I never introduce her to anyone that I’m interested in, or sleeping with. To be fair, I don’t usually introduce any of my friends to anyone. And for good reason, as you’ll find out. So I call Ron, and he says yep, he’ll come get us.

Ron shows up and we get into his truck and head to the north end to drop my friend off. The entire way there, she makes jokes about me, asks him inappropriate questions, and shares waayyyy too much about my life. The next day she tells me she now understands why I never introduce her to anyone that I’m interested in.

After we drop her off, we head back downtown to my house. When we get there, he parks and comments on how he has a very nice down-blouse view. I may have had a slightly tasteless amount of buttons undone on my shirt. He leans over and kisses me. He’s a very good kisser. I kiss him back, hard. And then pull away and say, Thanks for the ride! And hop out of the truck. Goddamn prick tease.

He texts me the next day to tell me how much he enjoyed making out with me, and wants to see me again. But my schedule doesn’t work for the next few days for going out, so I say we’ll have to plan for the next week. Well, the next evening I have free happens to be Thursday again. And I’m going out. Again, he tells me to call him if I need a ride. Obviously I call him. Drunk Amy already made a hypocrite out of Sober Amy, so why the hell wouldn’t I? And once again, he drives all the way to the north end to drop my friend off, and then back downtown to drop me off. This time, I have my hand on his thigh when we make out in his truck. And by thigh, I mean upper thigh. And by upper thigh, I mean his dick. He seemed to like that. I’m sure he would have liked it even more if I hadn’t gotten out and gone inside my house alone again.

We keep trying to make plans, but again, my schedule is not always conducive to making dates. I make some time for him before one of my night shifts and stop by his house on my way to work. Well, his apartment. It’s weird how a simple thing like taking your shirt off leads to having a dick in your mouth, but who am I to stop the natural progression of things? He already had a cock ring over his dick and balls. And what he really wanted to do was jerk off while looking at me, so that was easy enough, plus I like watching guys jerk off. I told him he could cum on me if he wanted, and that then he should lick it off after. He didn’t like that idea. And he calls himself kinky! I laughed, I thought it was a great idea! He came on himself.

So then I left because I didn’t have time to hang around and do anything that would get me off. But I was relatively turned on by the experience. Not enough to see him again though. After hanging out with him soberly, I wasn’t that interested. Plus, he was 41 and still renting. The older I get, the more I realize the things that are really important in a man: Real Estate and RRSP’s.

We didn’t talk much after that. He texted a couple of times and I didn’t respond. And then a couple weeks after that, he found me on Pof AND Tinder again and messaged me on both. He told me he lost his phone or some bullshit like that and to text him and left his number. I didn’t text.


Don’t Play it Again, Sam

It’s been a month since I ended things with Sam. He was alright. On paper, he had a lot of qualities that I look for. But in reality, he wasn’t for me. On our first date, he paid. Points for that. But then he didn’t tip our waitress! I peeked at our bill and it was around $39. He handed her $40 and told her to keep the change. I saw the look on her face. The look that said she wished she had spit in our food.

The more I talked to him, the more bored I got. There wasn’t anything that excited me about this guy. I got to the point very quickly where I didn’t even notice when we went a couple of days without texting. And then when I did realize it, I didn’t bother sending him a message. I just didn’t care if we spoke or not. I was even past the point of seeing if there was anything physical between us that would spark some feelings in me. But then I got drunk.

I was out at O’Hanlon’s, a local pub, on a Thursday evening, and I needed a ride home. So obviously I called Sam. I told him to take me to his house, but insisted we drive through the park first where I made him pull over several times to make out. When we finally got to his house, he was pretty worked up and it didn’t’ take long for us to get naked. The sex was…ok. It wasn’t bad, it wasn’t good, it was just…ok. It did not make me want to do it again and again. 2 minutes after he came (I didn’t), I said, “Ok, take me home now please.” He looked at me and asked if I wanted to spend the night or at least stay and cuddle for a bit. Nope, home please.

He drove me home and I get inside and get ready for bed and he texts me. He texts me kissy faces and hearts. Fuck. I’m kind of an asshole.

We text off and on for a couple of days, my responses to him are short. I try to figure out the best way to tell him I’m not interested. I felt that since I’d already done a bang and bail, maybe I should wait a few days before telling him I didn’t want to see him anymore. You know, not destroy his ego. So I waited. And then a few days passed where I didn’t hear from him. Whew! I was in the clear! Yeah right. On the Monday of the August long weekend, he messaged me to see how my weekend had gone. I answered and responded with the same question. He told me it was good, but would have been so much better if he’d been able to see me because he missed me. Goddamn it. I was really going to have to have “the talk.”

It’s not you, it’s me, blah blah blah. What I actually said was “That’s sweet, but I have just not been feeling a real spark between us. I like you, but not in a romantic way and I don’t want you to waste your time on me.” His response was, “Oh k well good enough. Its cool, you straighten things out with the other party.” Other party? Wtf does that mean? Does he think I was seeing someone else? Obviously that’s the only reason I couldn’t be interested, right? I guess I didn’t need to be worried about his ego! *eyeroll*

Sam. And Calm Your Tits.

Ok, I wasn’t going to write about Sam right away, but given the feedback I’ve gotten about my last post, I think I should, just so you know that I do actually talk to/date nice men too. Before I begin Sam’s story though, let me address and maybe alleviate some of your concerns.
This blog will take whatever direction I choose. I haven’t written about weight loss in awhile because there hasn’t really been any. When I feel comfortable writing about that again, I will. My dating stories are a part of my life that I do like writing about. Admittedly, sometimes I do go along with the experience because it makes for a better story. I write for myself, but I also write for my readers, and I feel it’s important to be as honest as I can while still keeping some things just for me. And that is why I tell the sad stories and the frustrating stories, as well as the funny and uplifting. I stated in the beginning of my last post that I wasn’t sure I even wanted to share it because I was slightly embarrassed about how long I kept in contact with him. I could have easily kept the story of the doctor to myself, or edited it to make myself look more empowered and like I live a “take no bullshit” kind of life. But that’s a lie. I mean, I do try to do that most of the time, but I don’t always succeed. I make mistakes, I make poor decisions. But they’re my mistakes and my decisions. Not every man I meet is a contender for the same thing. If you aren’t single in the age of internet dating and disposable relationships, consider yourself lucky.

You don’t have to understand my journey, and I don’t have to define what I’m looking for as an absolute at all times. I’ve invited you along for the ride, and it’s not always going to be smooth. But I promise that it will always pull an emotion out of you. If I can elicit a response, whether it be a laugh, admiration, concern, anger, sadness, whatever, then I feel good about writing about it. Please keep reading and discussing :)

Now, let’s talk about Sam. My memories of meeting him are foggy at best. It was a Thursday night and I had consumed a cocktail or two and was at a club I had not been to before. He recognized me from Pof and with encouragement from my friend, came over to talk to me. I don’t know what we talked about, but I gave him my card to call me sometime lol He called me that night, and texted me. (There was another number on my phone when I woke up the next morning that I didn’t recognize. It turns out my friend gave my number to a different guy. She thinks she’s really funny.) I responded to his texts the next day and had him send me a picture since I couldn’t remember what he looked like. He’s pretty good looking. I agreed to go out with him, based on my friend telling me about her conversation with him and how nice he seemed.

Sam is 30, tall, handsome, ambitious, educated, straightforward, sweet, and kind of funny. He is originally from South Africa, but has been in Canada for 5 or 6 years now. He has a brother in the country as well, and the rest of his family currently lives in the UK. He is finishing his masters in finance and already has a job in his chosen field, as well as a parttime job doing sound and lighting at events around the city. He has big plans for his career, as well as having a family. Oh, I almost forgot the most important/impressive thing about him. He has not once, not ever, sent me a picture of his dick! After being in current dating world as long as I have, it takes so little to impress me! He wants to know what I think about things, we have real conversations. Although, I think he’s still trying to figure me out. I’m a little quiet on a first date, and I think some of my answers to his questions threw him off a bit. But it seems to be intriguing to him. He can’t figure me out so he wants to know more. I’m unintentionally mysterious.

We have gone out twice now. Once just for a drive around the city, and once out for supper and a drive around the park. He paid for supper, big points! Somehow, both these instances ended up with us at his place. Funny how that works. I enjoy making out with him. He’s a good kisser. He’s very affectionate and complimentary. It’s nice. And yet, the second time we made out, he told me how much he likes me and how I’m his dream woman and even though it’s too soon, he already knows he wants to pursue a relationship with me. And all I could think was, “but there’s still other men I want to have sex with!” Now, I don’t need advice on this, so please refrain. What I am doing now is trying to figure out if this is just cold feet at the thought of actually being a relationship with someone, or if I’m just not feeling it. I don’t have butterflies when I think about him or I see him. I’m not excited about the next time I get to see him. I am not fantasizing about him. A whole day went by where we didn’t text and it didn’t even occur to me until I went to bed that I hadn’t talked to him all day (he did text after I’d gone to bed and he had been at his second job). But, I don’t dread the thought of seeing him again. I’m just sort of…ambivalent about it right now. So I’m going to see him again. Probably this weekend. Both times we’ve made out, I did go home wet, so I think at the very least, it’s worth pursuing that physical attraction, right?! 

The Doctor

Well, here’s another example of the kind of men I get to meet through online dating. The doctor was young, handsome, ambitious, owned his own home (with a pool!), and generally had his shit together. On paper, he was pretty great. In reality, the more I talked to him, the more magic he lost. I’m almost embarrassed with how long I kept talking to him. But I’m going to relay some of our conversations anyways. My life is nothing if not full of potential dating embarrassment.

A: Hi ****
D: Hey! Amy?
A: The one and only
D: My future gf?
A: Correct
D: I see you’re tall as well that’s awesome :)
A: As are you! I like tall men

And our conversation continued on like that for awhile. Flirty, getting to know each other.

D: When can I take you out? Do you want marriage and family?
A: I don’t want them on a first date, but yes I do lol
How is your Friday looking?

D: Spending time with you! And falling in love with you
A: Hahaha It’s true, I’m quite easy to fall in love with

More flirting, questions about family, backgrounds, etc. Then:

D: Ya I haven’t had sex in a year and a half
A: Really?! How come?
D: I don’t do hookups
A: Fair enough
D: I’m hung though
A: Hahahahahaha Thanks for throwing that in there
D: *SENDS DICK PIC* Handle that?
A: Omg, are we at dick pics already?
D: I’ll leave you alone
A: Why? I’m not offended by it, but it was a little early to send it, especially without any warning. An right after you tell me you don’t do hookups
D: Good luck I feel bad now. I’d think it’s best if we stop talking. I need someone who’s open. I’m sorry
A: Lol I sell sex toys as a part time job and write a blog sharing my dating and sexual experiences. I’m open.
D: So you won’t even give me a chance?
A: You just said you didn’t want to keep talking to me…
D: I do if you do if we date you’ll blog about our sex life?
A: Haha Not necessarily, unless it’s to brag
D: Haha ok. How many partners have you had?
A: I’m not going to answer that one. Do you usually establish the gf/bf status before you have sex?
D: Yes. I Don’t do hook ups.

So, to recap, normal conversation, dick pic, he thinks I need to be more “open” to receiving pictures of a stranger’s dick, even though he doesn’t do hookups, then we keep talking. This was in the afternoon on a Monday. We end our conversation and pick it back up in the evening. We enter the conversation after he’s asked me for a naked picture, or at least topless, and I say no. When he says it’s not fair because I’ve already seen him naked, I tell him that wasn’t my choice to see that. He was a little offended by that lol Because he’s allowed to be offended when he sends me a picture of his dick and I don’t fall to my knees thanking the heavens for sending this man into my life!

D: Ps not impressed. I need a woman who’s all over me
A: You expect an awful lot from a first conversation with someone who hasn’t even met you yet. I don’t think I’m being unreasonable not to want to send you nude pictures of myself yet
D: When can I meet you?
A: I’m off tomorrow, I work Wednesday and Thursday nights, and I’m off Friday.
D: Friday works. Skinny dipping?
A: Lol Lets start with drinks or supper and see where the night takes us. That pool does look very inviting though
D: Good lord you’re impossible I’m used to woman being all over me
A: That’s not me. I think you’re really good looking and I like what you’ve told me about yourself, but I’m not going to throw myself at you.
D: K. Good luck Amy
A: Is that a goodbye?
D: Yup
A: Ok, take care.
D: You too. If you want me you have my number
A: I never said I didn’t want you.
D: Hm
A: Just because I don’t behave the way you’re used to doesn’t mean I don’t want you. From what you’ve said so far, I get the feeling I am very different from the women you’re used to. I won’t apologize for being who I am, and I won’t do anything I don’t want to do. If I’m not for you, I’m not for you.
D: I’m just used to woman being all over me
A: Because you’re a handsome doctor?
D: Apparently that doesn’t matter
A: To everyone? Or to me?
D: You
A: Is that all you are? I think you have substance beyond that, but it’s contradictory to tell me you’re not interested in hookups, but then treat me like that’s all you’re interested in. I’m trying to get to know you (since you’re not going to sleep with me anyways u less we’re dating) and you’re pouting because I won’t show you my tits.
Or Is that the kind of woman you’re looking for? One who doesn’t care who you are, as long as you’re a hot Dr?
D: Hmmm :(
A: I am blatantly telling you I’m interested. I don’t know what more you want. I want to go out with you on Friday. Are you in or out?
D: In

I know, you’re probably wondering why I even bothered continuing this conversation. I didn’t include the stuff where he told me about his family and where he’s from and his little jokes. The things that made me like him. Trust me, beyond all the bullshit, he actually had some charm. Plus, after this conversation, he called me to apologize for being a dick and that earned him some points. And he apologized again once we hung up.

D: I sincerely want to thank you, for calling me on my asshole attitude. It’s time my wall comes down not every woman is out to hurt or use me. Sex will be amazing I understand though it’s only a part of love. :)
A: Lol you’re welcome. If there’s one thing you can count on with me, it’s to call you on your bullshit and keep you grounded.
And no, I’m not out to hurt or use you or anyone.

We chatted throughout the week, but every day was the same thing. We would have normal conversation, and then he would take it just a little too far. And then get pissed because I didn’t react the way he wanted me to or expected me to. Every day was a day he apologized to me after I told him off. The next day, I woke up with the WORST pain in my neck and shoulders. I must have slept funny and maybe pinched a nerve or something. I went back to bed, and by the time I woke up again around lunch, I had a fever, I was nauseous, and I had the chills. I felt terrible. I chatted with the doctor for a bit when I first woke up and he was nice at the time. Asked if I needed anything, etc. Then, he texts me in the afternoon. I respond back with a hello and how tired I still am, and he calls me. He calls me while he’s jerking off! He asks me to help him and join him. I laugh and say no, and the little fucker hangs up on me! And then texts me.

D: delete me
A: I told you not to treat me like a hookup. I tell you I’m in pain today and not feeling good and your reaction is to call me while you’re jerking off? Yes, I will delete you. You’re not the guy you say you are.
D: Yes I am. I just expect a woman to give me what I want. That’s why you’re single
A: Oh don’t even. We talked about this yesterday and I told you then that I’m not going to be the girl who strokes your ego for you.
D: your loss
A: I’ll take it
D: Wow You keep on blogging about your sex life, weirdo
A: What? You think I should be fighting for you after the shit you just pulled? Again? I’ve been talking to you for less than 24 hours and you’ve told me to lose your number twice already. There are tons of girls on Pof who would love to suck your dick and have phone sex with you today. I’m not one of them. I’m the woman who planned on dressing up for you in Friday and making you laugh and thought maybe, just maybe, you weren’t a Pof douche like so many others. And now you resort to name calling. I was wrong, you are too young for me. Good luck. I hope you find the things you think you need.
D: Lol I just expect woman to be all over me
A: *eyeroll* yeah you mentioned that.
D: Maybe I don’t know how to build a relationship without sex.
A: You’re not going to find a quality woman by treating them the way you’ve been treating me. Is that what you think of me? That I’m just some whore, here to get you off?
D: No. Never thought that, usually woman will do what I ask I’m not used to push back
A: Yeah, well, that’s how you make me feel. Thanks for that. You keep talking about sex, you sent me a Dick pic, and you called me while you were jerking off. Not cool. You couldn’t even wait the 4 goddamn days until our date.
D: bitch please. Go back to your fairy tale life
A: My fairy tale where I don’t see a man’s dick until after I’ve met him? Sounds good to me. Bye.
D: See ya. I can do better anyways I don’t need a woman who tells me no.
D: It’s too bad you didn’t even give me a chance
A: I did. You fucked both of them up.
D: I don’t see how to me you’re passing on an amazing guy
A: You’ve shown me that side of you just part of the time. I liked that side of you. The rest of the time you’ve been a prick and treated me with zero respect. You fall into name calling when you don’t get your way. I can’t be with someone when I’m not sure how they’re going to react to the word “no”.
D: Ok some woman will understand
A: Some woman will be your doormat. Don’t message me again unless you’re sure you want who I am and not because you’re hoping I can be some idea of who a woman should be.
D: Ok. When you’re finished being a bitch you have my number. If I don’t hear from you within 72 hours I’ll delete you, assuming you’re not interested.
A: Why wait? You can do it now. I don’t spend time with men who call a woman “bitch.” Speaking my mind doesn’t make me a bitch and I have not called you any names or been cruel. Being mean to me isn’t going to turn me on or make me want you.
D: You don’t understand you’re supposed to be all over me I’m the best you could get
A: Lol i understand that’s what you think. It must be killing you that I’m willing to let you go, just like that.
D: Nah it’s cool
A: Ok good. Then stop talking to me. I’m obviously not who you want.

Ok, ok. I know. You’re reading this and scratching your head wondering why I’m even bothering telling this guy what a dumbass he is. Did I mention he’s a good-looking doctor with a pool and it’s summer in Saskatchewan right now?

D: Sorry :(
D: Amy?
A: What?
D: I have feelings for you
A: Then why do you behave the way you do?
D: Because I’m horny I’m sorry fuck ive laid in bed, Crying
A: Horny is a really bad excuse. What are you sorry for? Do you understand why I’m upset?
D: Yes. I disrespected you
A: How? I need you to say it
D: By demeaning you, I think you’d love phone sex though
A: It’s not about me loving it or not. It’s timing. If we were to start dating, would I have to worry about you freaking out every time I said no to something? We shouldn’t have had this many apologies before we’ve even met
D: I agree. Honestly I’m not as bad I as seem I’m very insecure and you, were someone I felt comfortable with. I’m sorry I feel like shit
D: I have so much to give I’m tired of being lonely. The way I treated you is so out of character for me I don’t know where that came from I’m ashamed
A: My forgiveness is endless, but you’re really fucking testing it.
D: So eventually when we have sex I have to be damn good, and provide you with an unforgettable first date
A: No, I don’t need you to try and impress me with a bunch of crazy stuff. Just be yourself, and show me you care by being a good guy and thinking before you speak/text. Because seriously, resorting to name calling? I do not want that relationship and I won’t enter into one like that, or stay in one like that. I think better of myself. And I will happily support you and build you up, but it will be on my terms.
A: It’s really hard for me to tell you how awesome you when you’re already doing it yourself
D: No I was an asshole I was less than awesome
A: I agree

Then he shared with me some stories about his past, his losses, things he’s been through. Tugged at my little heart strings.

A: Sharing these things is going to make me want you, not calling me when you’re masturbating and then hanging up on me. I want you to know that I can let everything that’s happened go, if you never treat me that way again. Ever.

And once again, everything was good. Until it wasn’t. He once again got upset when I wouldn’t have phone sex with him. And then messaged me the next day like nothing happened.

D: How’s work
A: Whatever game you’re playing, I’m not interested. I don’t want to do this with you every day where you don’t get your way and stomp off like a petulant child and then come back like nothing happened. Don’t message me again.
D: Your loss. Could of had me
A: It’s “could’ve”, and I’m well aware what I could have had. I don’t want it.
D: Why not I’m stud, educated.
A: Don’t forget selfish and insecure
D: Insecure sure, right woman will work on that with me
A: *sigh* then go find her and leave me alone. You could probably start with a 1-900 number since that’s such a big requirement for you.
D: So you’re saying you wouldn’t work on my insecurities with me?
A: No, I won’t. When did we start talking? Monday? Tell me anything nice you’ve said to me, tell me one conversation we’ve had that wasn’t all about you and your needs. Tell me why I should want to do anything with you when you tell me to fuck off in a daily basis because I’m not the right woman for you. Tell me all of that.
I am a laid-back, go with the flow, forgiving, optimistic person and you are driving me crazy.
D: So be mine
A: That’s all I get? No.
D: You’ll come back they always do
A: No. You’re the one who keeps messaging me.
D: Maybe because I want you
A: Then fucking act like it.
D: Wow
D: Can I have another chance?
A: Why do you even want one?
D: Because we have chemistry let’s go out and see what happens
A: What’s going to happen if I do or say something you don’t like?
D: Haha. We’ll deal with it.
A: If I agree to go out with you, I need to know you’re going to be a gentleman. I am not going to talk about sex with you until we get to the point of having it.
A: But, if you’re still available tomorrow, that’s only one day you have to wait. One day. Can you do it?
D: Not sure. Have date tomorrow. Because you weren’t interested.
A: Lol Ok, then I guess you’ll have to wait longer. Maybe she’ll be the love of your life. And then we’ll never meet and this won’t matter anyways
D: True. Well she seems genuinely interested. And doesn’t snap about sex
A: Did she have phone sex with you?
D: Haha yup. She started it
A: Of course. I bet you loved that. I hope it works out for you.
D: Thank you. I do feel bad, we didn’t even have a good chat
A: No, we didn’t. I wonder why that was…
D: But as Brooke says “You’re smart and dreamy. Any woman’s crazy for not being all over you.”
A: She sounds lovely. Seriously, good luck.
D: If it doesn’t work tomorrow want me to let you know?
A: I won’t be available for a date until next week
D: Why
A: Because I’m not going to wait around for you to figure out if things are going to work out with another girl. I’m going to make plans. And then I’m gone out of town the rest of the weekend.
D: Ah. Ok. You didn’t want me anyways
A: Right. That’s why I keep talking to you and agreeing to give you more chances. Because this whole roller coaster is super fun for me.
D: It sucks I’ll cancel my date tomorrow

So, the doctor tells me he’s going to cancel his date with this other girl and take me out. Frankly, I didn’t believe him and made backup plans. He’s a rollercoaster of emotion. Plus, it’s not cool to cancel on a date to take someone else out. It’s a good thing I did make other plans, because guess who suddenly stopped texting me back around 4pm on Friday afternoon when we had a date at 6? Yeah. Prick. Oh well. After the first couple of days of getting to know this guy, I was already worn down and looking ahead to what kind of story this would make. He did not text me again to apologize or anything like that, but he did message me the next week saying “hi”. I did not respond.

The end to that week was a perfect depiction of my love life. I talk to this little prick all week, and he ends up standing me up, I’m at an event and a man I like shows up with his new girlfriend, and the guy I’ve been trying to coordinate my schedule with so we can have sex messaged me to hook up and I had started my period. Oh, I got fucked all right. It just wasn’t any fun.

I have somewhat better news with a man I’ve gone a couple dates with. I’ll tell you about him soon.