Reader question #50: I’m a 27-year-old virgin and I’m mostly okay with that but sometimes I feel like a loser.

Luke Skywalker
We’re all pretty sure he’s a virgin, but does it ever come up?

Here is  a reader question and corresponding guest-post from Commander Logic on the subject of losing your virginity after most people around you have lost theirs, but really it’s like a manual on dating and respecting the shit out of yourself, aka, universally applicable.

Dear Captain Awkward:

There are a lot of awkward conversations going to be going on in my future. Hopefully, at least.

Here’s the story:

I’m a 27 female post-graduate student at a German university (I’m German.).  I’ve never had a boyfriend (I may never have) and all the guys who were ever interested in me (not many) were sadly not my type. There was one I really liked, too, but he was as shy as me where feelings and touching were concerned and in the end another girl (who was a lot more outgoing) dated him and I was not interested anymore. Another guy I met on the internet actually kissed me on our second (and last) date – right in the middle of the lively market place of my little university town. He never called again – me neither.

Other than that I had some three crushes. One of those I actually tried to talk to (I had a crush on him for two years). We flirted a lot in class – he actually sat next to me on purpose (I think) and touched my hand “by accident” a lot. I really liked that. But when I tried talking to him I totally felt stupid and couldn’t really impress him, I guess.

Last year there was a Japanese guy I totally found hot and we had many nice dates with talking and walking. But when he confessed that he liked me a lot, I totally panicked. I wasn’t happy at all!! I went home, cried and was totally disturbed. I wrote our university counseling because now I was absolutely sure that I was a whacko and not right in my mind. Since then I’ve been there for a few times and it really helps me, but basically there is nothing much wrong with me. (Thank god.) The Japanese guy turned out to have more problems than me and we try to stay friends but sometimes that is really hard, too, because he wants me to adopt every opinion he has about certain things I feel very strongly about.

Anyways, my problem stays the same: I seem to have certain fears concerning relationships and run away fast, when there is a guy in sight who might actually be interested in me. I’m certainly not an anti-sexual type. I know my needs and have a normal amount (I guess) of sex with myself, where I fantasize about doing it with a man. I dream about a relationship with cuddling and lots of kissing. I love romantic movies (but I fear they have given me a very unrealistic stance on the whole concept). And lately as more and more friends are starting families with children I came to realize that I really, really want to have babies sometime soon (but not too soon and not without an actual father to those children).

But I also more and more realize that I’m way too late. I left out the whole teenager drama years because I was mobbed at school and would rather have died than let anyone know that I actually liked the guy who started bad rumors about me. I was always good at school but sadly also always slightly overweight, which gave good opportunity for children to harass me. My self-confidence was never very high for that matter. (I actually felt really great with myself for the first time when I attended a one month exchange program at Virginia. At that high school I wasn’t really the fat little pig anymore and guys actually talked to me and were nice to me.) My parents actually wanted me to change my school but I didn’t want to lose against “those people” and I finished with the fourth highest grade.


Princess Leia from A New Hope
May or may not be a virgin. Has awesome hair, a gun, and Han Solo, so who cares?

At university I thought that everything would change. Well, it did in a way. Especially after studying one year in Tokyo, Japan, I’ve become far more self-confident and actually a lot “girlier” as I started to wear decent make-up and am constantly looking for a good style for me. But I realized that I’m not the party-type and I really don’t think it necessary to get drunk to have fun. My friends seldom had boyfriends either, so there was seldom any male company to our come togethers. By the way, I may be 27 years old, but I’m not very tall (1.58 m) and look a lot younger (I’m constantly asked for my identity card when buying DVDs which are rated 16 (German scale) or alcohol (which you can’t buy when you’re younger than 18 in Germany).

Well, after telling you all of this I want to ask you what I can do. Especially since I started to fear that a man in my future might laugh at me for never having had sex before. I’m really starting to get afraid, which adds to my clumsiness when talking to potential boyfriend material. A friend of mine told me to not tell that I never had sex before. But he would know, wouldn’t he? How is such an awkward conversation to be mastered?

Reading this I feel like crying for being such a loser in the whole love business. I would love to hear from you.

Hello Fellow Virgin-by-Circumstance!

Commander Logic here, and let me lay down my bona fides here:

At 27 I, too, was a virgin.  I was good-looking, if a little overweight, and at 31 am still both those things (Ed. note:  Commander Logic is TEH HOTNESS).  I had skipped the whole dating thing in high school and half of college.  By the time I was ready to date in college, everyone seemed either hooked up permanently, or had relegated me to Kid Sister status.  I went on two dates with one guy, and had month-long “relationships” with two others, none of this leading to sex or even close.

I mean, I wanted to have sex!  I did!  But I had two things working against me:

1. I was very serious about being completely honest about being a virgin.
2. I wanted to be emotionally involved with the first guy I had sex with.

Both are laudable, right?  Not totally crazy things to want?  And yet, I would tell a guy I’m dating, “Hey, I’m a virgin!” and he would immediately employ the fade out.  I didn’t know it at the time, but after talking to many, many male friends and exes about this issue, I’ve determined that – contrary to social expectation – most men are TERRIFIED of virgins.  Inside their heads it sounds like some part of this: “What if I screw up?  What if I hurt her and she never wants to have sex with anyone again?  I’ll RUIN HER LIFE WITH MY PENIS! What if I can’t make her orgasm? SHE’LL NEVER ORGASM! Oh man, and I bet afterward she’ll be completely in love with me and she’ll INSIST we get married and have kids and AUUUUUUGGGGHHHHHHHHH!”  And all of this is on top of whatever sexual anxieties they usually have.  So in retrospect, I get that my program of complete honesty and forthrightness was scaring the crap out of my would-be suitors.  But I can guarantee you that none of your would-be boyfriends will be laughing AT you if you tell them.  Nervous laughter, perhaps, but nothing malicious.

Steve Carrell from the 40 Year Old Virgin

My friends had a few suggestions that I am sure you are familiar with:

Don’t tell him you’re a virgin!

But I’m scared! What if I do something wrong?  And isn’t that lying by omission?  He should know!

Just pick up some guy at the bar and take him home and BANG HIM. Get it over with!  How about that guy?
No.  Just… ew.

Do you have any single guy friends? See if they’d help you out!
Ehhhhhh, no.  Because then things would be… WEIRD.

None of these are bad solutions, by the way.  But they were all wrong for me, and I don’t think virginity was actually the problem.  The problem was that I was not out in the dating scene primarily to have sex.  I wanted love.  Cuddling.  Jokes.  Warm nights on the couch watching movies while it rained outside.  And sex, sure, but that other stuff way more!  So here’s the part where we get down to your (and my) actual problem: How to date in order to find love instead of in order to get laid.

From the tone of your letter, I suspect that you’re looking for love, and you view your virginity as a big road block in your way.  To that I say, nonsense!  First of all, congratulations, you come equipped with an Asshole Detector most people our age do not possess.  If you do end up telling a suitor, “Hey, can we take it slow?  I’m kind of new to the whole sex thing,” and he responds negatively (or creepily positively) then you know that he is an asshole who does not deserve you.  AND THEN YOU MOVE ON.

The answer to our problem isn’t sex, it’s dating.  A lot.  Get an online dating profile, and if you like someone, go meet them for coffee or at a bookshop (buy each other a book, great first date!) or at an ice cream shop or whatever for 30 minutes.  If that goes badly, you say goodbye forever and move on.  If that goes well, go on a bigger date.  If that goes well, keep dating.  Kiss your dates.  Make out with them.  Hold their hands.  Dump them after three dates.  Dump them after a year.  Let them feel you up in movie theaters.  Massage their thighs in movie theaters.  And if you like them That Way, and they seem good at the kissing and feeling up, tell them you’re not very experienced at sex, but would like to try it with them.  The point of dating is not sex.  The point of dating is not even love.  The point of dating is to get to know a person well enough that love and/or sex are possible.

Because virginity doesn’t define you.  You are not a 27-year-old-virgin.  You are 27-year-old-YOU.  You, who has been to Japan!  You, who can take care of her own sexual needs!  You, who kissed a guy in a marketplace that you never called!  You, who breaks hearts!  You who has had your heart bruised!  You who wants love and maybe babies but not right now and definitely a wonderful life with someone!

And you can find love.  It is manifestly not too late.  It is not too late now, and it will not be too late ten, twenty, or fifty years from now.

I finally lost my virginity when I was 27.  It was to a man I did not tell about my virginity straight out, though I alluded that I was not very experienced. It was… not great.  It hurt.  And sex kept hurting.  But I had no frame of reference, so I figured I was just doing it wrong, but couldn’t explain to him what the problem was.  He broke up with me.  I told him he was my first, hoping that it would make him…. guilty perhaps?  It was juvenile of me, but I was hurt and sad.  And I went on my way.  He did not deserve me.

Then I found love.

Okay, FIRST I went on a lot more first dates, fewer second dates, and maybe two third dates, but this guy.  This man loved me.  He waited for me to be ready to have sex with him.  He was gentle and kind. He didn’t care if I’d had one other partner or one hundred, which I know because he said that.  He loved ME.  When he looked at me, he didn’t see hot-chick-I-want-to-bang or even near-virgin-who-is-pure, he saw Commander Logic (Who is super hot, and also makes hilarious jokes, and loves Doctor Who, and has great taste in beer, etc). (Ed. note:  All of these things are true.)

I married that man last year.  We have a condo and two cats and so much love that it sickens people who walk by. For the record, sex is awesome and does not hurt.

That might happen to you.  But what happens to you will probably be a lot different!  Maybe you’ll date exactly one guy and you’ll fall in love and then have seventeen babies with him.  Maybe you’ll lose your virginity to a super sexy 53-year-old tour guide from Spain and then leave him and become a Berlin accountant’s mistress.  Maybe you’ll date sexlessly for 17 years, but have a BLAST doing it and then sell your memoirs for a million euros.  Maybe the 22-year-old delivery boy will develop a mad crush on you and you’ll have a torrid love affair and then leave him for his older, hotter brother.  Maybe you’ll teach or take a night class and befriend a student who is sweet and sincere and wins your heart, and you get a flat together, never marry, but never need to.

There is no one way to live your life or fall in love, so it is impossible to lose at love or life.

You are not defined by your virginity.

You are wonderful and complex.

And seriously, when you are online dating, meet up after no more than three email exchanges.  Penpals will never have sex.

Commander Logic OUT.

25 thoughts on “Reader question #50: I’m a 27-year-old virgin and I’m mostly okay with that but sometimes I feel like a loser.

  1. I like this answer so much! There’s a lot to think about here, but I think the LW should be aware that a lot of people out there who have the whole “having a lot of sex” thing figured out, still don’t have the dating for love thing figured out any more than she does. If what you want is a loving, lasting relationship, one night stands won’t necessarily* get you there anymore than celibacy will!

    *Disclaimer: my current bf started out as a one-night stand, so sometimes those definitely work out also… not trying to put ’em down.

  2. In my experience, virgin sex is bad sex: the first time you fuck, it’s going to be terrible. You might not come, he might not come, you might not fit together for no apparent reason, you might not lube up, you might accidentally bite his cock and on and on. It’s okay, it happens to everyone. Go in expecting a learning experience, not a transcedental melding of souls. (That happens later. 🙂 )




      I almost don’t feel so bad now…

      1. I have had sex with six virgins (nerd fetish ftw) and 100% of the time the sex has been awful. Even in the guys who turned out to be superb in bed later!

        I think it’s the nervousness, the inexperience and the expectations that make it so terrible…

        1. I feel like there is a “sex with six virgins” tongue twister to be had here.

          I think that bad first-time sex with someone you really like (and intend to sleep with again to take advantage of the learning curve) isn’t really all that bad.

      2. I think most people would say “My first time was really weird.” Good sex takes a lot of trust, practice, good will, humor, etc.

  3. Dear Commander Logic,
    (and Capt. Awkward Team)

    Thank you so much for answering my self-pitying mail.
    You are so right – I’m me. The way I am.

    And I made some choices in my life that lead to this. Yes, I’m searching for THE feeling called LOVE and am growing anxious where it is hiding.
    Plus German guys (and Japanese, too) really can’t talk to women in general. I talked to an Italian exchange student last week, and she was complaining that no guy here ever speaks up to a girl he likes and asked me why’s that. Well, how I wish I knew.

    I guess as a girl I have to take matters to my hand from now one. Dating you say- dating it’ll be.

    Another fun fact: 1 1/2 ago I met a guy via Internet and we met. We are still meeting as friends and we are talking about a lot of stuff including sex. He actually told me the time we met that he didn’t wanted a relationship just now, but we could be friends with benefits. Boy, was I mad. Normally he would have been sent to “Never see you again”land by me, but then I thought a male friend for a change would come in handy and we’re having lots of fun. But just not in bed. I told him that and he is okay with that.

    Thanks again for answering me!! *hugs to you*
    And all the best to you.

    Greeting from Germany.

    1. V by C, you sound pretty awesome. Apparently you’re smart, and tri-lingual (at least), and when it comes to stuff that makes you unhappy you meet that stuff head on (not settling for the wrong boys and asking VERY smart people for VERY good advice).

      Stay awesome, and everything’s going to work out, no doubt about it.

    2. First, you sound like you’re doing AWESOME. Especially with your friend who requested benefits, which you declined. Bravo for knowing exactly what you wanted and not giving way!

      Plus German guys (and Japanese, too) really can’t talk to women in general.

      Also, American guys. Basically, Guys, the kind of guys you and I wanted to date? TERRIBLE at picking up women. This is why the internet dating site is your friend: all the power of rejection is yours without having to face rejection in person.

      But I also recommend a TON of non-committal dating because it makes the process of finding The Love less daunting. It’s like (pardon the extremely girly comparison) trying on pants. Pants shopping is HARD. But when you try on pants, and they don’t work out, it’s not because your butt is too big/small/round/flat or because the pants are AWFUL. You and those pants are just not right for each other. And that’s okay. There are pants out there for you and a butt out there for those pants.

      So next time you’re faced with a cute dude you’d like to have coffee with, remember that the worst he can say is no. And if he says no, then he was the wrong pants for you, and you move on to the next pair cute guy.

      Repeat: “Hey, I’m going to go [place] at [time]. Would you like to join me?”

    3. It was a great question, V by C, and the feedback via email and the Twitter is “OMG, me too, I thought I was the only one.” You’re obviously cool, just, you’ve been focused on your studies (rightly) and higher education is a very small and odd dating pool. Hopefully you can make this a summer of awesome dating?

  4. Oh, man, so much good advice! There really needs to be more advice out there for people in this situation. I know this, because I was really worried about losing my virginity at 23 (still not that old, I know, but old enough that mentioning it could have been awkward). But I can’t write good advice like this, because I really did just want sex and not a relationship, and eventually I went out and got exactly that — and then after six months of messing around with various different guys, I decided that now that I knew a bit more about sex, the sex wasn’t as urgent and maybe a relationship would be nice, too. Which worked our beautifully for me, but I get that losing your virginity to a random guy you met at a party isn’t for everyone.

    So, yeah, I’m really pleased to read some good advice for older virgins who are more interested in relationships than I was. It’s absolutely possible to get past the ‘virgin’ thing and enjoy your sexuality (and/or companionship) with another person in your own way.

  5. I think this is fantastic advice. I am quickly approaching 26 and have never had vaginal sex. I’ve had a couple sexual partners, who, when told that I was still a virgin, ranged from over-excited to very respectful. While not all my partners were necessarily good choices, I learned a lot about sex and men, and learned that I have the right to say “no” if I’m uncomfortable, regardless of the situation. I don’t know when I will finally have sex, but I don’t worry about it. I’ve gained enough experience to know what I like, through encounters with partners and with myself. I think, V by C, if you know yourself, and what you’re looking for, you’ll be in a much better spot when you find it. That’s what I’m hoping for.

  6. Commander Logic is highly decorated with medals commemorating her badassery, and bravery in awesomeness. (salutes)

  7. This is fantazmic. Thank you Commander Logic! 😀 This is also just what I needed to hear (well technically read…but, you get the point! haha) I’m seventeen and have been a little down in the dumps because I look around and every friend I have is in a relationship and ‘gettin sum’. I realize now that it was just the teenage hormones going to my head. I have a whole lotta life ahead of me and it should be fun not awkward and desperate. 🙂 I do like a guy but I don’t know if I want a relationship or sex right now and that’s okay right? Is it okay that I don’t want to change my life just to feel normal in comparison to my friends? I just keep having this irrational fear that I’ll be alone forever because I’m alone right now and flighty right now. Bizarre. Again, I blame the hormones, but maybe I shouldn’t? eeeeeee

    1. Don’t change your life to feel normal in comparison to your friends. Have sex IF and ONLY if having sex with that person at that time will make YOU happy and feels right to you (and your partner).

    2. You’re so amazingly welcome!

      Yes, it is okay to be single at any age. It is also okay to be single, be cool with being single, but also sometimes feel sad about being single. It is totally normal to simultaneously WANT something and also NOT WANT it. Confusing? FOR SURE. But also normal and okay and you will be okay.

      You will not be alone forever if you don’t date someone in the next week, month, or year. Heck, even if you DO date someone in the next year, pfft. You may never see them again after you graduate high school or college or whatever you plan to do next.

      Focus on you for now, and only do stuff you are 100% HOORAY about doing. ❤

Comments are closed.