Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

The (Almost) 40 Year Old Virgin

So last night I was talking with friends about one of our relatives. He doesn’t read this , doesn’t even know about it, we think. But I’m going to be discreet and not include too many biographical details, just because.

He’s almost 40. And as far as anyone knows, a . In fact, we’re all pretty much 100% certain of it.

Back in his 20s, he used to talk about wanting a . Frequently, in fact.  But he never got one. Has never had one.

And like anything else in life, the longer you let a problem (I realize that sounds VERY judgmental, calling his virginity a problem, but that’s not what I mean) fester the harder it is to eventually deal with it.

You see, this guy is painfully . PAINFULLY . And yet back, 15 years ago he used to force himself to go to “singles” types events in the hopes that something would magically happen. But nothing even did.  Because in addition to being , he’s the kind of person who doesn’t really know how to take the initiative in social situations.  He waits for people to talk to him.  Waits for other people to make decisions. Waits and waits and waits.

Anyway, we were talking about it last night and the fact that we all wished there was something we could DO. To help. But the truth is, what could a friend or relative do (in real life, not in a movie)?  Force him to go to the gym and take better care of himself and then hire a matchmaker? That’s the other thing, in his 20s he could’ve passed for cute but he’s completely stopped taking care of himself in recent years, making a bad situation even worse. I must admit joking about hiring him a hooker (not seriously, more theoretically). But his issue isn’t so much about sex but the social/romantic stuff that goes with dating.

As is so often the case, I have no point.  No advice or moral to this story. I’d love to hear what others think.  Do you know people like him, and if so, do you know anyone who was able to get their social/romantic shit together late(r) in life?  I’d like to think he can and believe it’s never too late, for anyone/anything. Right now, though, his situation just makes me shake my head.

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20 to “The (Almost) 40 Year Old Virgin”

  1. Kelly says:

    My first thought was “I wonder if he has Aspergers?”

  2. trininista says:

    Awww. this is so sad. Has he tried online dating already? seems like the pretty obvious choice for a shy person who has trouble socialising in real life. Great opening platform to get to sell yourself, meet people.
    And what about speed dating? That may be too much if he is very very shy, but he would not have to initiate contact. It’s done for you, right? So sad.

    • Simone Grant says:

      I’m a huge fan for online dating. Huge.

      One thing about it, though. It requires effort and some confidence. He completely lacks the latter and hasn’t made any of the former in years.

      I think it’s sad, too.

  3. Terry says:

    My brother is 60 – shy in his own way. But here’s the thing- sometimes we don’t know what people really do – or they are really like. Some are simply not kissing and telling.

    Oh yes- my brother is single- always been a bachelor – lives in the middle of Alaska (Copper Center). Good looking, smart, dry wit – and caring. We don’t talk about his personal life – he doesn’t bring it up. Not many women up there- and certainly not much intelligent life in that part of Alaska. Other than an occasional bit of cabin fever from the long winters — he doesn’t complain about his life. But- it could be my brother is dating a lot- but I doubt it.

    What to do? Nothing. Think about it- I occasionally ask advice of others, but hate when people interfere with my life.

    Just imagine- he may be enjoying his weekend more than most of us –

    • Simone Grant says:

      I like your version of the story much better. Much, much better. I would love to think that he’s been off having fun all these years, and just not sharing the info with friends and family. LOVE IT!

      And you’re right. Asking advice does not mean you want others to meddle.

  4. Sandyvs says:

    In this situation, which is kind of sad from MY view point (but maybe not his…..) I would say you can’t miss something you never had. Sometimes I almost wish I’d never had that unbelievable mind blowing experience with that certain guy because it kind of ruined it for any others. ‘Sometimes’.
    I, myself, if I was living in close proximity to that relative would start inviting that person to do small little things with me, as well as inviting him/her to join in some of the group things I do. Not all the time, but occasionally when I think it may be something they would enjoy. If they join in fine, if not, fine. It may even enrich my life as well.

    • Simone Grant says:

      I agree, it’s hard to miss what you’ve never had.

      As to your suggestion, we’ve all done that with him – w/o any success. But I guess it might have been seen as “meddling”….

  5. Kelly says:

    Hmm, this is a tough one. This might sound cliche, but I feel like if there was something he enjoyed doing—cooking or tennis or something, that putting more time into an activity might bring him out. Then he’s at least doing something he likes/ is comfortable with, rather than online dating or going to singles parties (which can make the most socially awkward people even more shy). It’s a hard thing to approach, but maybe worth a try.

    • Simone Grant says:

      I think it’s always good for people to spend time doing the things they love, and if that never turns into a date so be it. Which is kind of what’s happened with him. He has pursued hobbies, etc over the years (he’s not a hermit). But because he’s afraid to actually ask a woman out, well…

  6. Black Iris says:

    I don’t have any stories of people working these things out, but I think there are things he could do that might help with his shyness. Toastmasters helps people overcome a fear of public speaking. He could get therapy or some kind of coaching to help him learn to talk to people first. He could look for a single’s scene that fits his real interests more than forcing himself to go to a bar. It might even be something a little outside the norm like the Society for Creative Anachronism. I would focus on the shyness first, not the appearance. There’s someone for everyone and it might be more helpful to remind him of that than to push him to diet or anything. The first thing to do, though, is to find out how he feels about his life and whether or not he is having more of a sex life than you realize. One final thought – if the sex itself has become an issue, there are people who work with sex therapists and have sex with single men who need to work on sexual problems. Much better option than a prostitute.

    • Simone Grant says:

      The prostitute was not a legit idea, as I mentioned, it was a joke amongst concerned family/friends.

      Those are all thoughtful ideas. I would, however, disagree with you on one big point. You say there is someone for everyone. I disagree. I don’t believe there is a someone for everyone. Some people go there whole lives without falling in love. Others fall in love many times. Some will stay single forever. Others will marry multiple times.

      I am concerned about this man because he’s a decent guy and if he wishes to date and meet women then I want him to be fulfilled. And maybe, once he gets started, he’ll meet someone special. Maybe not.

      Someone for everyone is a frequently unhelpful way of looking dating and mating.

      • Black Iris says:

        I don’t believe that there is a someone for everyone as in “you have a soul mate out there.” I was thinking more that if you want a relationship, you can find a decent person who has enough in common with you and wants to be with you. In this case, I was thinking about your comment that he’d let himself go physically. I don’t think that would make it impossible to find someone to love.

        As far as marrying multiple times goes, I think that actually sometimes comes from the thinking that there is one person destined for you. Then when things get tough, you might assume you found the wrong person.

  7. Matt says:

    You mention that he actively wanted a girlfriend in his 20’s to the point that he talked openly about it and went to singles events. I’m curious: does he still mention that he wants a girlfriend? Does he show any signs that he’s not happy with his current situation?

    It seems like someone could only get to the point in life that you’re describing if (1) they genuinely didn’t care about their “problem” (I find this unlikely, because almost all humans are wired for companionship) or (2) they had met so much failure that they have started to believe they can *never* get a girlfriend, no matter what they do.

    There’s lots of information and more than a few talented people out there who can help people with those kinds of issues, if the person wants help; it seems like his real “problem” is not admitting to himself he wants to have companionship. Like they say: you can lead a horse to trough, but you can’t make him drink.

    Do you know how he feels about his situation?

    • Simone Grant says:

      Have I asked him recently, no. I know that he experienced rejection in the past and respond well to it.

      As I’m sure you know, not everyone who needs help seeks it out. Many people (maybe most) just ignore their problems and hope that things will magically get better.

  8. Ben says:

    I turned 40 this year and got the “40 years old virgin” dvd as my best friend’s gift. It was a joke that he “had to do” even though it was obvious. A few people I know know about my status since I am not (and they are not) troubled by it.

    How I got here is part shyness, part fear of rejection, part waiting for a time when I would be economically stable, part not wanting to have my little soldier take control of my brain, part not wanting to wear a seduction mask, part wanting to do my part to change the world, part feeling it’s too late, part looking for myself.

    There are lots of reasons, each playing it’s role. I plan on writing a book about how I got here. I hope it will make others understand why some people are like me, but it will also be a philosophical look at society in general.

    As for your friend’s shyness, I can only say that there’s a high probability that neither you nor your friends can easily help him with it. He has to make choices. And until he decides to do something and accept that he may puke like me on a date and may have to take calming pills you probably will have to wait to help him.

  9. anitha says:

    Hi Ben, I am your female counterpart. I feel your “pain” (pardon me for calling it that). This status isn’t such a stigma in some societies as it is in others. I, for one, am a hopeless romantic and feel that the physical and emotional commitment ought to go together. Know anyone who’s interested in starting a dating club for people like us, also perhaps believe in marriage and commitment and then carrying out the act?

    • Ben says:

      Hello Anitha,
      it’s funny that you should mention a dating club because I’ve made a little research while thinking about my book and thought that after finishing the book I would start a 25+ virgin dating web site since I haven’t found any on the net. But instead of waiting to finish the book I will start working on it today and hope to have it at least functional (if not finished) in one or two months.

      The site will be more than a V dating site, it will also be a support group. So we will be able to discuss with people like us in forums about “the art of dating”, places to date and meet people, do’s and don’ts, I will ask a few non-Vs to answer our questions about tips on dating and how to prepare for when comes the moment to “do it”, and lots more. It will be a site for people like us to build our self-confidence and self-image and gain some dating experience with a recommended (but not obligatory) monthly “friendly” date where we will date with about anyone on the site without looking for a relationship, just to become more comfortable going out with the opposite sex. It will be a place where we will be able to help and support each other and hopefully find love.

      If you would like to help me work on the site (not necessarily in making the site itsef) but how it should work and what it should contain, you can contact me here:

  10. Katie says:

    Yes I know one. He lives in Brighton. Mid 30s never has kissed a girl or had a girlfriend. I think men who don’t take care of themselves or who are clueless will never get that girl. Also it seems a lot of older men here in Britain still are with their parents, I mean as a girl I don’t think I would have a relationship with a guy who shared his kitchen or bathroom with his parents.

    I wish your relative the best luck. But how do we know society and family lets say didn’t push him into that role – to look for a girlfriend?

    Maybe he isn’t interested in girls? but thats just my opinion.

  11. Interesting post! I have a friend who I worry will end up in this situation! We are in our mid-twenties, and the girl has never been on a date before. I’ve dragged her out to go clubbing, bars, etc. but she has never hooked up with a guy or even been on a date. But she wants a boyfriend and I feel like she is depressed because she does not date :(