I’m now the 31-year-old virgin and I still haven’t caught a break.  But I’ve finally landed another date.  Only took me a little over two months.  I’m sure the holidays are partly to blame, but it’s been exceptionally difficult to get a date lately.  I’ve been hitting OkCupid hard over the past few weeks, but conversation after conversation flatlines.  That seems to be my main problem.   I don’t seem to be saying the right things to hold anyone’s interest or taking the conversation in the right directions.  Instead I seem to fall into a boring rut of discussing work/school/family and all that bullshit and then things stagnate.

I’ve gotten more responses and first messages and dates than other virgin guys my age could dream of, but I still have nothing to show for it. It frustrates me to think that there are guys literally half my age getting laid.  How are they doing it?  How are they pulling it off?  They’re just dumb fucking teenagers, what kind of game could they possibly have?  Well… more than I have, apparently.

But I managed to work some magic with Art Girl.  She’s 28 and does art therapy with patients suffering from traumatic brain injuries.  We exchanged a few messages, moved to texting, and then we set a date at a crepe place.  I got there a few minutes before she did and mentally patted myself on the back for my choice of venue.  It was very cozy and comfortable.

When she walked in shortly afterwards I stood up to greet her.  I cringed inwardly a bit as I shook her hand, wondering if I should have given her a hug instead.  But I just moved right on and led her to the counter.  It was our first time there so we took a few minutes deciding what to get.  I told her to get whatever she wanted because it was on me.

“Aw, that’s nice of you,” she said.  I wrinkled my nose at that.  Usually when a girl says you’re “nice,” that’s not a good sign.

We finally placed our order and sat down.  I was curious about what her job entailed, but after a couple of minutes it was clear she wasn’t interested in discussing it in detail.  She confessed that after getting 400 messages asking “What’s art therapy?” the topic was beginning to wear on her.  Understandable, but I joked that she’s drawing so much interest because she’s the only one on the site who isn’t a teacher, nurse, or social worker.  From there we started talking about online dating and comparing our experiences – the sites we’ve tried, the messages we’ve received, the dates we’ve been on… I learned that she’s been on the site for two months and I’m only the third guy she’s gone on a date with.

I also learned that she doesn’t like or want kids either, so we were able to bond over that as well.  By that point we were finished with our crepes and smoothies, so I asked her if she was up for a game of Jenga.  There was an array of board games in the shop and that one was simple and fun enough.  She accepted the challenge and we played three games before she called it a night.  Already?  We’d only been there for an hour.

“Yeah, I gotta get home and check on my dog,” she said.

I laughed.  “That’s usually not a good sign…”

She laughed too.  “I’m sorry, I’m just really attached to my dog and I haven’t been home all day.  I was having dinner with my parents earlier.”  We spent a few minutes talking about her dog and then she stood up to leave.  I followed suit, with a sinking feeling that this evening did not go as well as I thought or hoped.

We walked outside.  Out on the sidewalk I said, “So do you still want to check out the museum this weekend?”  She turned to face me.  I had the sense that if I hadn’t said anything she would have continued on towards her car unabated.

“Potentially,” she said.  Potentially.  Yeah, I’ve heard that before.  “I have to check my book and see what I’m doing, I’m so scatterbrained I can’t remember what’s going on that weekend.”

“Okay,” I said.  Meanwhile that had been my original proposal.  Her schedule didn’t work out this past weekend, but she had told me she was definitely free this coming weekend. So I had suggested the crepe place in the meantime.  And now she was saying she didn’t know?  Looked like this was headed for another dead end.

“You said you were free either day…?” she asked me.  I answered in the affirmative and she said she’d let me know, and I said I’d talk to her soon.  Then we hugged and parted ways.  So maybe there will be a second date, but it doesn’t exactly sound promising.  And she was so hot, too.  It’s been less than 24 hours since our date – any advice as to what I should say when I contact her?  Should I even?


In other news, I reached out to a girl who “fell ill” at the last minute and wanted to take a rain check. Just as I did with the others who pulled the same stunt, I wished her well and told her to let me know when she was up for our date. Two weeks went by and I dropped her a line to see how she was doing and ask about rescheduling.  No response, just as expected.  At least four other girls deleted their profiles in the middle of our conversations.  I was texting another girl but I couldn’t pin her down on a date despite coming up with a plan and a time, so I just gave up.  And there’s one I’m talking to right now and we’re in the midst of setting up a date for this weekend.  So we’ll see.

First dates:  26
Second dates:  3
Third dates:  2
Cancellations:  5
Stood up:  2
First kisses: 1
Sexual experiences:  0.6

45 thoughts on “31

  1. And she was so hot, too. It’s been less than 24 hours since our date – any advice as to what I should say when I contact her? Should I even?

    Don’t. You’ve put your cards on the table – you set a date and told her when you will be free. Now it’s down to her to confirm. If she’s interested, she will come back to you.

    I’m sometimes wonder whether you are letting your suspicion show just a little too much. If a girl is in two minds about seeing you, being challenged on what she said earlier is not going to make her come down on the side of seeing you again. You might be coming across as controlling.

    I know why you are suspicious, and I understand – I would be too. We’ve all been stood up by flakes and messed around, we’ve all had a woman have a mysterious illness on the day of the date or have a family emergency, but you can’t let it show. You can’t make each girl feel guilty about the last one who messed you around.

    That’s just my view anyway.

    • I don’t know if I’d call it suspicious… more like accepting reality and understanding that she probably isn’t interested. I didn’t challenge her on anything she said, I just left it at “okay, let me know.”

      I guess it is down to her to confirm. Which means I should probably go ahead and make other plans for the weekend.

  2. The problem is that you can’t force it with these girls. Put yourself in their shoes. They are inundated with male attention. You are one of dozens, maybe even hundreds of guys messaging them or asking them out online, at school, and at work. Their default is to reject you, because they have to. Sending a follow up text makes you out to be just like every other needy, whiny guy she’s encountered and had to avoid. Believe me, if a woman wants you she will let you know. She will text, call, and basically stalk you. If there is any doubt or ambiguity, then she isn’t all that interested and you need to walk away.

    I think the only way you are going to succeed is to cultivate a large number of female friendships and acquaintances and stop trying. Eventually some girl will see you as a viable option as long as you keep yourself together and reasonably employed.

    Single men generally have far fewer sexual partners and way longer dry spells than women, so accept it. It’s not as much of a problem as you think it is. I’m sure most women aren’t stupid and are aware they have a lot more “experience” than the guys they eventually settle down with. So you’re not alone. A bit extreme I’ll agree, but hardly all that unique.

    • Really? I’ve never heard of a girl stalking a guy she’s interested in, unless she was 16 or something. I don’t think they really do that at this age. They generally expect men to be the pursuers. Maybe some women can jump in on this here?

      When it comes to Art Girl, I’m agreeing with CUCH and just sitting back and waiting to hear from her. But I don’t know about your broader advice to stop trying and essentially just wait for something to happen. If you’ve gotten to my age and haven’t met someone through work/school/circle of friends, you don’t really have much choice but to make the effort and put yourself out there.

      I agree – it does feel a bit forced at times, and that’s a consequence of my unforunate circumstance. Most people lose their virginities in their teens/early 20s and kick off what’s generally thought of as a “normal” sex and dating life. Here I am at 31 trying to achieve the same end because it didn’t happen organically and naturally like it did with the majority of people my age. Now it’s like something akin to a planned government project instead.

      Women have a lot more experience than the guys they settle down with…? I’ve never heard that before. I thought it was the other way around, no?

      • A woman will stalk a man at any age and in any era if she really wants him. If they are only on the fence and would possibly date them if the stars aligned then they probably wouldn’t show much interest and the guy would have to take more initiative.

        • Still not buying it. Like I said, I have yet to hear of any woman “stalking” a man she’s interested in. Because if that’s true, then why do I hear nothing but women complaining about waiting on tenterhooks for a guy to call or text?

      • It’s true my experience is only anecdotal and unique to me, but since I tend to believe in the law of universality, it must be the same for many since in most areas of life I’m pretty average.

        My 1st was at 25 and I was her 1st. I lost contact with her after we broke up, but I heard she slept around post break up. Not really an option for me. I have no idea how many guys she slept with, but I’m pretty sure it was more than 5 and probably waay higher than that.

        Out of respect for my wife I won’t say how many guys she slept with before we met….and remember this was before the days of online dating….but I was shocked. And she thought she was bit of a prude.

        The 3rd. Maybe a dozen. She never wanted to say, so I think it must have been many more.

        It seems odd because there is a pretty evenly split gender ratio, but I suppose there are some guys out there having all the fun. Plus women can more easily date outside their age range so their pool is bigger. It’s just a guess on my part on why it works. Also the difference isn’t all that great if you think about it. A few one night stands, a few fwb arrangements, maybe a slutty phase after a bad break up, and few longer relationships and it adds up by the time a girl is 30 if she’s still single. So it’s not as if women are banging new guys all the time, but just once and a while.

        As for women stalking you, absolutely. Pretty much every relationship I’ve been in, or my close friends have been in have been initiated by the girl. My first girlfriend hunted me down. My current wife did the same. She did everything she could to manipulate us into being together….we worked at the same company and she was friends with the HR lady. When my marriage fell off the rails there was another woman waiting. Endless texting and manipulation on her part brought us together. She wanted me and made it happen.

        On top of all those, there have been others that made their interest blatantly known, but I was not in a position to take up with them. My point is that I did “chase” a few girls when I was younger with embarrassing results. I was lucky in that I had female co-workers where we started out as friends first so there was no pressure to make a strong impression on a first date.

      • Stalk- hopefully not in person like following you, etc, but she’s definitely going to Google your name and search for you on all social media. Women are strange creatures, I speak as one, and even the littlest thing can halt our interest in someone new. Hence the reason I try not to “stalk” someone until they give me reason, lol. (I get to know them and something’s not right so to social media I go. Not proud of it…which is why I’m actively not using Facebook this year, and limiting other social media I’m on to once a day for a very small time allowance.)

        • Stalking means different things to men and women. For women its creepy and maybe dangerous. For guys it’s mostly flattering. All depends on perspective. I’ll use the example of my wife. We worked together and she admitted much later she did everything she could to put herself near me. We lived in staff housing…different houses….and she even had the guy in charge of housing put me in her house. I was completely oblivious. I thought it was good luck she was always around.

          • I still feel like that’s unique rather than the norm for women to do that. Maybe someone can share a similar story. But if that is typical… then that’s really discouraging. I’ve only ever had that kind of attention once in my life – when I was 17. And we know how that story ended.

        • “Even the littlest thing can halt our interest in someone new.” This touches on something which really annoys me, which is that often there seems to be little if any room for error with women. Within five minutes of meeting you they’re fast-forwarding the relationship in their heads and they’ve already accepted or rejected you by the time the appetizers have arrived. At least that’s how it seems to me. Like they don’t even give you a chance. I’ve been more than willing to overlook things and ask for first or second dates, yet some folks will tell me that I’m being way too picky and I should try lowering my standards. ::scratches head::

          It’s actually damn near impossible to stalk me. I’m self-employed and work alone. I have no Twitter or Instagram. I don’t use my real last name on Facebook and it’s private anyway. Even if you knew my real last name, nothing comes up in a Google search. Whether that’s a good thing or bad thing to women, I have no idea, but I like to think it makes me mysterious and alluring.

          • A lot of stems from not wanting to make a mistake by getting involved with the wrong person, or that’s my guess anyway. I’m not saying it’s right by any means.
            I’ve given guys a chance, one in particular. We had a good vibe going via text, and then when we hung out, I knew it was going nowhere. I mean, I had a blast playing pool with him, and we hung out a few other times. Just any romantic interest just wasn’t there for me. And then he turned around and flat out lied that I came onto him for sex, which was the other way around, and I had said no.
            And I don’t know what the point of that was…
            Ah okay, well then it’s nothing they’re looking up. Maybe that’s their concern. Haha jk

          • you’re smarter than me with social media. also i feel the way you do about those women who fast forward the whole relationship in their head. the way they accept or reject unsuspecting dudes is head spinning.

            • I’m a fucking wizard when it comes to first messages. It’s everything that comes after that I’m still working on. But if you ever want to message a girl on a dating site and get a response, I can probably help.

  3. I don’t think you should quit, but you need to be realistic. Perhaps develop a cold detachment about it all so you don’t feel burned all the time. I can only guess why you haven’t caught fire with one of these girls. I assume it’s because they have so many options their default position is “no, not interested”. Whatever the reason is it doesn’t matter: the common thread is they aren’t really a viable option for you and there has been no evidence you are the guy able to break down their walls.

    It may take some time, but at some point some girl will take interest in you and you will know it right away. She’ll call, text back, and make 2nd date happen.

    • I didn’t say anything about quitting? I’m certainly continuing to forge ahead. I’m still bummed when things don’t work out, but I don’t get pissed off about things like I did in the past. Maybe their default is to say “not interested” but I think it has more to do with honing my conversation skills. I thought this most recent date flowed better than most of the others.

  4. Ok, you know my style of coaching. Maybe, just maybe, it might help to add a little attitude to what you say and how you say it. Not mean, just a little playful boldness. If what you’re currently doing isn’t working, might help to change your approach. In person and on online dating messaging.

  5. Also, instead of the usual dating interview questions, family/work/whatever, might help to think of something different “tell me about a great vacation you’ve taken, Jill.” “Why?” “Because I’m curious to see what you enjoy. I’ll go next, I promise”

  6. Also, the nice comment. First of all, I’d say the lesson is don’t say that you’ll pay for her, because it’s implied. She may pull out her purse at the end, just pull the bill first and coolly say “I got it.”

  7. Sorry it didn’t work out with Art Girl. Maybe next time wait a day or two before suggesting to go out again. At the end of the date, you can just say something along the lines of… “this was nice, hopefully we can do it again sometime.” Both guys and girls like the chase a bit at the very beginning. 😉 Hope the date this weekend goes well!

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