“I’m a Below Average 31-Year-Old Virgin”

I’m a 31-year-old female who has never been in a relationship, been on a date, or had sex. Recently, though, I met a guy during a work event, he asked for my number, and he immediately started texting me the moment I got home. We got along just fine and started making plans. I was, of course, over the moon to finally get the attention of a nice man who seemed genuinely interested in me. But then, recently, during a conversation I said jokingly, “You must think I am the craziest,” to which he responded: “I wouldn’t say you are the most ‘anything’ woman I have ever met.” Which I interpreted as “every woman I have met was more than you are in some way.”

Now, I by no means think I am the prettiest — in fact, I have been told by many of those closest to me that I am fairly below average — nor do I think I am the smartest, funniest, or the superlative of any other attribute people look for in a mate. But I sure would like to think the guy I am dating thinks I’m special in some way. Is that too much to ask? So I am left between thinking “let it go, You’re lucky enough that someone has actually asked you out” and “I’d rather be lonely than be with a guy who thinks I am less than every women he’s very known.”

Am I blowing this out of proportion? Please help me understand. — Below Average

Yeah, you’re blowing this out of proportion. You are looking for a reason to let this guy go and end this relationship before it even begins. And I can only imagine that’s because you’re afraid of being vulnerable and getting hurt. And I can’t say I blame you if the people closest to you are the kinds of people who would tell you that you’re below average. I can’t say I blame you for being in a rush to find someone who will assure you that they’re wrong — that you’re special, actually. But I CAN blame you for testing a potential match and running because his response to some dumb rhetorical question wasn’t straight out of a rom-com. He didn’t have the perfect reply to you because he wasn’t following a script written by a screenwriter creating the shy heroine’s goofy-but-sweet love interest who is about to launch her into a whirlwind romance. But that doesn’t mean he thinks you aren’t special.

Don’t run. Give this a chance. See where it takes you. Open your heart. Let yourself risk potential hurt for the thrill of potential love. Quit looking for signs of this guy’s feelings for you and take time getting to know each other. Maybe he hasn’t even decided HOW he feels yet because he’s still learning who you are. Maybe your question threw him because it was an invitation to say something about how he sees you and he isn’t ready to share his perspective yet.

I’m sorry that you’ve been told by people closest to you, either implicitly or explicitly, that you aren’t special. I’m sorry you believe what you’ve been told, so much so that you’d let some off-the-cuff reply to a dumb question override the actions that show that this man has, as you said, “genuine interest” in you. If this guy truly thought you were nothing special, he wouldn’t have asked for your number and he wouldn’t have texted you immediately and made plans with you and invested in getting to know you.

I understand you have no relationship experience and that what you have with this guy so far may not look like the peeks you’ve had into other relationships, either through books or movies or Facebook posts or the things people have shared with you which are never the full picture of reality, but that doesn’t mean this can’t be great and real and wonderful.

Reality isn’t perfect. Love isn’t smooth. Relationships — even the very best ones — don’t have guarantees. And though you may think being lonely is preferable to getting hurt, it’s not. Because when you stay lonely on principle, you rob yourself of some of the great joys and simple pleasures of life: sharing a sunset with someone you care about; watching his chest rise and fall in the quiet of the morning; sharing inside jokes; having coffee made for you just the way you like it. And so many more things. Staying lonely because you’re afraid of being hurt is lame. Don’t be lame. That’s even worse than not being special.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Great advice, Wendy. I actually took his comment in a different way. Most guys are worried that the women they’re interested in are “crazy” in some way. He may have meant you’re a nice normal girl who’s not overly confrontational or dramatic or loud or annoying or any host of negative characteristics he’s encountered in women before. Conversely you’re also not the shyest, the quietest, the least interesting, etc. “The girl next door” quality is what most men want in a long-term partner and it sounds like you’ve got that. I agree with Wendy in that you shouldn’t overthink one little comment and should see where this relationship takes you.

  2. What does below average even mean? And what kind of friends and family even say that? I think you need new friends, LW.

  3. i agree with Wendy’s comments and would also add that although it feels awesome to be wanted, it is perfectly fine to NOT get involved with the first man who shows interest as well. Think of this as a situation that could lead anywhere. Most likely, like ANY flirtation…with supermodels, with average folks, it might not end in a lifelong loving partnership but very well might lead to an interesting and positive experience and if he seems nice, is most likely worth the risk. His view of you is not the definitive say on your value as a partner.

  4. Looks are not that important. They really aren’t. However, you have internalized a lot of bullshit about yourself. You’re not special. You’re not smart. You’re not attractive. You have internalized this stuff and it has become your identity, how you see yourself and portray yourself. Your letter is full of fear and self-hatred. You shouldn’t be surprised that if that is how you present yourself to the world, lots of people will accept that view. Confidence is the sexiest. Believe in yourself, that you have something unique to offer. I’m not the best-looking guy. I’m smart, but I don’t agree with most people on many things. But i have something to offer – no one is quite like me. Believe in yourself and allow yourself to be vulnerable and you might get hurt. Or you might find love. Or friendship. Or you might not. But if you are not willing to risk being hurt, you definitely won’t find love.

  5. I’m going to copy-paste my answer here in hopes the LW sees it:
    My boyfriend calls these ‘minefield questions’ and refuses to answer them, because…what good can ever come of them?:) Really, what are you trying to achieve by asking someone if they think you’re ‘the craziest’?
    He probably wasn’t thinking *anything* along those lines – and then you asked for validation out of the blue and he probably thought ‘wow- where is this coming from?’. So he tried to be nice and deflect with a friendly, generic version of ‘no, of course not’, which you didn’t take, because YOU fear that you’re crazy, or inadequate, or ‘below average’ – fears that he could never quell no matter what he did.
    On that front, I get where you’re coming from, because I’ve been there. But guess what, I didn’t want to STAY there. So I got into therapy. Did a lot of soul searching. Had some spiritual training. Read lots of books.
    My point is: please work on being a little less hard on yourself! Please look into ways to get you out of your negative mindset – (free) counselling, self help books, mantras, working out, spirituality; whatever you need. Your life happens NOW, and the time to experience and enjoy it is NOW. Anything that stands between you and being capable of doing that, seems huge but is *really* just a mental conviction/negative programming (like ‘I’m below average’. Seriously, my heart hurts to read that). And guess what…you can undo and overcome those. I promise! But, like Wendy said, you have to be willing to open your heart and be vulnerable, rather than sit there alone and thinking you know the (negative) outcome already.
    Oh, yeah, and what Diablo said. Confidence is the sexiest:).

  6. Laura Hope says:

    I was never the prettiest or the smartest but I always (usually) got the guy. Know why? Because when I was with someone, I gave them my full attention. Ever notice that when someone really gives you their attention, it kind of lights you up? And I’m not talking about fawning all over someone. I’m talking about really hearing them without losing yourself.

  7. I love your advice, Wendy! The last paragraph was awesome and so true.

    LW, Unfortunately you interpreted that in the most negative way possible. When I read it, I thought it was actually a good thing. Men in their thirties are probably looking for normal, as opposed to “the most.” You don’t want to have to compete to be the most anything. You just have to be yourself and if he likes who you are, give the relationship time to grow.

  8. Positive thinking is your friend. It takes a while to train your mind but just ignore negative things. Don’t ask loaded questions. Frame yourself in a positive light and pretty soon it will just come naturally.

  9. Avatar photo sobriquet says:

    I dunno, I’ve found that people don’t really WANT the prettiest/smartest/most anything mate because it creates an imbalance. People want someone who is a lot like them. Even if you are the most basic, normal person on the planet, when you are in a relationship with the right person, I guarantee you will end up feeling special (but, you know, give it a few dates, at least!).

  10. Ditch your lame friends who basically sound like assholes!

  11. Another Jen says:

    Completely agree with Wendy.

    Why would he be talking to you if he thought you were the craziest? By casting yourself in a bad light, you’re tacitly criticizing his judgement and decision to spend time with you. Not to mention, constantly reassuring someone of their worth isn’t fun…”you’re not crazy, you’re not unattractive, you’re not boring.”

    I’d recommend you lay off the self-depreciation. Try to pick out a few cool things about yourself and recognize them: you seem like a thoughtful and introspective person…you probably have a lot of interesting, well-considered ideas about the world. Interesting is good. People like talking to interesting people. You attracted a nice person’s interest at a work mixer…you must be friendly and approachable. People like friendly, approachable people.

    Also, try not to get caught up worrying about how pretty you are or aren’t. You don’t have to look like (or look better than) other people to have worth. Your smile is all your own, your laugh is all your own, your body and the way you move through the world is all your own, your style is all your own…it’s not a contest. Everyone has value. Everyone has beauty.

    Hope you give yourself and this guy a chance. Hope you figure out how to like yourself and have a little fun. Hope you find some friends that lift you up.

  12. bittergaymark says:

    Don’t go out with the guy. Find a therapist. Your reaction to his vague statement to your utterly moronic question reveals that you are — sadly, in mo position to date anybody. Period.

    1. Wendy (not Wendy) says:

      I think she can do both. As long as there’s birth control.

      Though, totally unfounded in this case, I do know men–women too, now that I think about it–who have a genius for finding that unloved, low self-esteem, average-looking woman who is thrilled to get some attention and easily manipulated into doing whatever they want (giving him blow jobs without any reciprocation, making him 365 sandwiches, getting murdered, etc). And I really hope that’s not what’s going on here.

  13. I just think, in addition to what I said on the forum thread, which was don’t set up guys to fail, don’t say you’re crazy to a guy you just met, and don’t judge him for his response to that dumb statement… You really need to let go of this “below average” thing. Like yesterday. That’s a construct that’s *in your head* and does not exist in reality. You need to be confident in the qualities that make you special and in what you can bring to a relationship. Stop with this “I compare unfavorably to everyone else” crap. I feel like maybe it’s kind of a convenient excuse at this point. You keep telling yourself that story to explain why you haven’t had more success in dating, but maybe it’s really how you relate to guys that’s the issue. Not being the prettiest or the smartest never held anyone back from finding a good relationship.

  14. Wow… and I thought that I was insecure!
    Cheezus Crust woman! It was a COMPLIMENT! He meant that you are not normal… because you are weird, awesome, pretty, smart, probably a dozen other things that other women, who did not make his cut, are.

  15. excuse me. Typo:
    *who didnt make his cut, arent.

  16. I am not sure how I got here, but the amount of people enjoying your misery and thinking you have to accept whatever comes your way just because you’re 31 baffle me. Do not listen to anybody who replied before me. Please.

    This person is using a Pick Up Artist tactic otherwise known as negging in order to make you feel insecure and do whatever he wants. And then he will likely dump you. You don’t want your first relationship to be this. You don’t want to be manipulated into having sex with the first willing stranger who came your way just to prove yourself that it’s possible and to fit into whatever is the others’ concept of normality.

    Also, virginity is a nonsensical concept in 2015. Most of us don’t have hymens by the end of puberty, sex dreams can count as sex, so can masturbation.

    I don’t think you need therapy, either. At least not for the reason that one of the posters just suggested.

    1. Avatar photo Dear Wendy says:

      Um, no, having a sex dream doesn’t count as losing your virginity.

      1. bittergaymark says:

        Wait, hold up. Let’s not be hasty! Surely this doesn’t mean that after winning no less than three Oscars last night in a wonderful dream — that I am somehow NOT an Oscar winner in real life?

      2. Anonymous says:

        I wouldn’t be surprised if “friend” is the LW.

      3. Does this mean that I didn’t *actually* make out with Hugh Jackman? (Even in my dream I told him we couldn’t go further because I didn’t want to cheat on my husband).

      4. Oh I’m screwed for sure…
        Also, some people owe me some real apologies!

    2. “You must think I am the craziest,” to which he responded: “I wouldn’t say you are the most ‘anything’ woman I have ever met.”

      I stand by my statement in the forums. Most people are a bit egocentric. I think the letter writer is awfully self-focused to take this line of text before ANY date and assume it’s an insult. I think you (friend) are pretty egotistical to dismiss every point of view that is different from your own bold assertion that this must be negging. My guess is that the guy was bragging about his level of experience. But this is VERY much a guess based on one line of text banter before any actual date.

      I don’t hear people telling the letter writer there is something wrong or embarrassing about being a Virgin. It’s the letter writer seems frustrated and unhappy about the situation. I think its invalidating to tell this woman her perception of her own sexuality or lack there of is a nonsensical concept. Maybe that’s true for you. But living with no human contact but my own would be a very lonely and frustrating experience for me.

      The woman could go to a therapist to help her change some negative thinking that might be holding her back. I don’t think anybody is ever going to say that is bad advice to a letter writer asking for help on any given topic.

      When I think back on what has given me confidence and self-esteem, it has usually come from experience. I’m no dating expert but the more I went out, the more I learned what I wanted and what I didn’t want in a partner. I got better at learning when my gut was right and when there was another issue at play. I learned even if I failed at something or someone rejected me I could live with it. The times my self esteem has been the lowest were usually times when I had stopped putting myself out there because I had let fear of not being enough stop me from taking any risks. It takes courage to put yourself out there and that is something worth being proud of.

      Letter writer, instead of worrying about if this is the “one” take the pressure off yourself. I still think you should dip your tones in the dating pool at least for a lunch if for nothing more than confidence-building. But that’s only if you like the guy and think you might have fun. And maybe he will be a douche. Thats the chance we take when we get to know someone new. Remember, this is a learning experience. Unless he’s deranged, even a faux pas will be better than never knowing. If you absolutely must, I suppose you could tease him about the comment and see how he responds.

      Of course if you are comfortable where you are and happy with your life, don’t worry about it. There are many women and men and other with limited or no romance in their lives that find their meaning and fulfillment in other ways. And its not like this is the last chance to ever go on a date. So if you aren’t ready, then go ahead and disregard. But do try to make steps towards developing confidence that you are a person worth being with.

    3. I read the letter a few times and I still can’t figure out why you think this guy is a pick-up artist. Isn’t introducing yourself to people and exchanging numbers something normal people do when they date? How else do you communicate?
      Also what Wendy said sex in dreams does not in any way count as losing your virginity. Just no.

    4. Avatar photo Cleopatra Jones says:

      Most of us don’t have hymens by the end of puberty
      Maybe I’m old and don’t know anything about the new fangled hymens of the younger generation but I’m sure this is an outright lie. Hymens stay intact if there’s no vaginal penetration, so if you don’t have intercourse until your 40’s, then you are still a virgin as it relates to having an intact hymen.

  17. dinoceros says:

    Who knows what he meant by that? If he enjoys spending time with you, then I think that’s more telling than anything.

    Though if you have loved ones who tell you that you’re below average, and you just go along with it, the lack of confidence that indicates is likely more unappealing than your actual looks or anything else. I have a friend who didn’t have a boyfriend until 31, but she never trashed herself. She knew she was awesome anyway, and now has a guy who appreciates her for that. If she ran around telling people she was below average and let her friends insult her, then I doubt he would think she was as fun and strong as he does.

  18. Avatar photo SavannahAnna says:

    “Craziest”? That is the form of being the “most” crazy person. He said you’re NOT. You jump straight to assuming that if you’re not this very negative thing to him, then you can’t possibly be anything positive either. That’s just not there in what he said to you. Give yourself, and him, a little more credit, please!

  19. Below average - yeah right! says:

    I am the original poster of this question, sorry I couldn’t figure out how to edit the original post so I am posting this as a comment.

    Thank you Wendy and all whom have replied for the tough love. I have read them over and over again and it struck me that for the longest time I have been a prisoner of the ghosts of my past. Of people that although are no longer in my life, I somehow continue to let what they have said or done define and decide my self worth and I am tired of it. Reading the comments, I sat down and made a list of everything I loved about my self and my life and realized there was plenty. I have landed my dream job, currently have a group of amazing friends, I am in the best shape of my life and generally just kicking ass at life. So starting today I have decided that rather than thinking “but why me” when approached by a guy, I will think “hell yeah me”. My self worth is mine to decide and I am done leaving it in the hands of others. Oh and about that guy, he’s taking me out this weekend 😉

    Thanks all.

    I am worth it.

    1. Awesome! Have fun on your date!!

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