What Does a 28-Year-Old Woman Need to Do to Lose Her Virginity?

What Does a 28-Year-Old Woman Need to Do to Lose Her Virginity

Dear Evan,

I’m a couple of years from 30 and still a virgin, but I’m not waiting for marriage. I’ve kept mine because going through high school and college it seemed like hookups were frequent topics of gossip and drama. Coming from small schools, I didn’t want any part of that even if I did want sex.

However, now I’m beyond fed up with my virginity. But, friends say that guys don’t want to be with a virgin, even when it comes to a hookup. That has me wondering what I’m going to have to do to lose it.

Should I go with what my friends say and lie to a guy that I just haven’t had it in a while and need him to be extra gentle? Go with a hookup app and be honest? Am I going to have to plan a trip to one of the countries where women pay to play?

Thanks for any insight!

Dear Jordan,

I’ve answered a number of questions about virginity before – and have discovered that when virgins search the internet to find validation for their abstinence, they often end up yelling at me.

Perhaps the chaste crowd will lighten up after reading your letter. Finally, a virgin who is not looking for validation of her choice, but someone who actually wants to lose her virginity.

You’ve come to the right place!

I may sound like a sex-positive former slut, but I was a virgin until I was 19. It certainly wasn’t for a lack of trying; it was mostly a lack of “game.” I went through my entire freshman year thinking that my best friends lost their virginity before I did, but, as it turns out, they all lied and I was the first.

Finally, a virgin who is not looking for validation of her choice, but someone who actually wants to lose her virginity.

Yeah, we were all pretty studly. But even though I wasn’t 28, I can empathize with your plight.

The problem when you’ve gone this long without having sex is that you’ve inadvertently made sex into this HUGE deal, when, in fact, it’s not that big a deal at all. (Not unless you’re part of the Christian abstinence crowd, that is). Sex is a really common, really fun way to pass a half-hour with someone you’re attracted to, and as long as you can handle the consequences, I highly recommend it.

But that’s the rub, isn’t it? Can you handle the consequences of a no-strings-attached hookup? Since lots of sexually active women can’t, I’m going to assume you should be more judicious in your choices.

So let’s go back to your original letter:

You’re “fed up” with your virginity and are wondering “what you have to do to lose it.”

I’m no math major, but this isn’t a hard problem to solve. Men want to have sex with women. As a subset of the group called women, you should really not lack in opportunity.

Should you lie to a guy (like your friends say) and say you haven’t had it in awhile?

No! Who are these friends, anyway? You’re a nice girl who has held out on sex a little longer than you’d like; that doesn’t mean you should just lie to a stranger and fuck away.

Slow down there, Jordan. You’re not desperate. You’re just horny.

Go with a hookup app and be honest? Plan a trip to one of the countries where women pay to play?

Slow down there, Jordan. You’re not desperate. You’re just horny. But if you’ve gone this long without having sex, you don’t have to waste it on a total stranger (like I did).

How about you do what many high school and college kids do (and what I recommend all of my 30-50something clients do)? Start dating someone. Fool around. Take him around the bases. Say you don’t sleep with anyone who is not your boyfriend. When he becomes your boyfriend, have sex with him. Wonder what the big deal was about. Have more sex. And get on with your life without all the worrying about how to lose your virginity.

Don’t go on a hook up app. Don’t fuck a stranger. Don’t hold out for love and marriage.

Get a boyfriend who treats you well and will call you the next day.

The rest will take care of itself.

Good luck.


  1. It was so good for me to read this! I’m a 36 year old woman who also happens to be a virgin. Like Jordan, I’m not exactly thrilled about that. But that’s the way it’s worked out for me. I was never holding out for marriage to have sex, but I also didn’t want to have sex with someone without commitment (ex., a boyfriend).
    Also like Jordan, I have a really hard time not making my virgin status into a really big deal in my mind. I think it’s because, at age 36, I’m well aware of how unusual this is. I’m embarrassed by it, honestly, and I dread having to explain it to guys. It doesn’t help that I’ve had more than a few guys respond with the “what’s wrong with you” kind of shock and bewilderment that just makes me feel, well, defective. I know I shouldn’t feel that way. But I do.
    On the other hand, I’ve also had the “virginity” conversation with some guys who initially seemed to be really great about it. Then I got encouraged and I thought, yay, this might be it – only to have the guy disappear on me before it even goes one kiss further. It always leaves me wondering what I did wrong or whether there’s some game being played here that I don’t know the rules to.
    Like Jordan, I’ve also had friends suggest that I just go throw my virginity away so that it’s no longer a hang-up for me. But, as Evan wisely pointed out, that can bring consequences far worse than being a virgin. The fact that I’m still a virgin tells you what side of that debate I land on.
    In the meantime I’m just trying to keep a positive attitude and to keep dating… while trying to beat back that nagging whisper in the back of my mind that says that I’m just not desirable to men. And that a man wouldn’t want to sleep with a woman who wouldn’t be able to please him in bed.
    Thanks for the great post, Evan! Best of luck to all of your readers as they navigate the dating world  ????

  2. It’s tough isn’t it, telling a man you have just met that you are a virgin. Just know that you are desirable to men, even if you are not so experienced as other women. And who says you can’t please him in bed? I am sure that if you are attracted to someone that you will have no problems in that area. Foreplay and sex, being good at it, is something you learn, not an inborn talent.
    I have had all the reactions possible, from them wondering whether i am deeply religious to ‘i don’t know what to say’, right down to thoughtless reactions a la ‘OMG, you are SO damaged’. Gee, thanks. Also, ‘bye.
    I have tried different ways of dropping the bomb and trial and error has shown to me that it is best to just keep the information to yourself for a while. If you slowly go round the bases then they do not need to know. If they ask whether you want to go all the way then you can in all sincerity say that you are just not ready for it, that you want to have sex if/when you are boyfriend and girlfriend. The big confession can wait until you get to know him better. Most dating situations never go that far, and you thereby evade the awkward conversation and their reaction to it altogether.
    If this feels deceptive, just think of Evan’s advice regarding sharing personal information about yourself. He said that he initially did not know about his girlfriend’s debt when they first started dating. She only told him after they had dated for a while. By then, he was so emotionally involved that he channeled his emotions and thought of a constructive way of dealing with it. He doubts whether he would have had the same balanced reaction if she had told him right at the start.
    The same goes for the virginity subject. It’s a very intimate subject, and you have the right to disclose it when you feel he is worthy. If he is involved with you on a more meaningful level, then he will be far more likely to tackle the subject sensitively, rather than giving a knee jerk reaction.

  3. Hi Jordan:
    I am also still a virgin at the grand old age of 35. In my case it has a slightly less benign reason, as i was assaulted when i was a child, which resulted in penetrative sex being next to impossible without a huge amount of pain. It is only in the past few years that psychotherapy and fysiotherapy has slowly made me ready for losing my virginity.
    It is deeply frustrating to know that everyone in your age group has so much more experience in this regard than you do. Fortunately, there is a whole lot of other VERY fun stuff to do in bed, so i don’t feel physically frustrated at all, it’s just that i wish i had experienced the grand finale at least once in my life.
    A year ago i was dating a guy who was racing towards sex without wishing to respect the fact that i wanted to take my sweet time going round the bases. He knew about my challenge regarding this matter, but looking back now i see he just didn’t give a flying fig, he just wanted to have his way asap. He was whining for it so much, that in the end i gave in and let him try. I had five seconds of feeling as if i was being stabbed with a knife before i managed to push him away. His reaction? To roll over and pout. That was when i knew that i wanted to get out of his bedroom and life pronto. It was a setback to my therapy progress which i had started a few months before, and it took me a while to get back on track again.
    You do not have this problem, but I would still caution against landing into bed with a random man. While it would be very tempting to lose it to the first guy that comes along. you have to ask yourself whether you would feel comfortable with that. It doesn’t have to be the most memorable experience ever (chances are that it won’t exactly be mind blowing the first time round), but wouldn’t it be better to experience it with a man you have a degree of intimacy with first? That you know well enough to know that he would be gentle and attentive, making sure it is a pleasurable experience for you? Finding out whether a man is capable of being this way towards you takes time. I hope you give yourself the space to find the right man to have this momentous occasion with.

  4. Emily, the original

    Jordan: I was a late bloomer myself. Pick a guy friend you like and trust. That’s what I did. I wasn’t in any way ga ga over him, and I didn’t want to date him, but he treated me well and we hooked up for about a month. That way, when you do meet someone you really like, you have a bit of experience under your belt and you won’t be so nervous.

  5. Hmmm… but Em
    Are you not the zombie queen? Doesn’t every male friend eventually fall in love with you and become a mindless zombie wanting Emily brain to date, to love and eventually to marry? (^_^)
    …   …   …
    I have heard of a few stories of people doing what you suggest, and almost all of them usually have at least one of the two (usually the test partner) fall real hard.
    I have never done it myself, but I do believe what the majority of people say when they say that friends with benefits rarely work.
    Besides aren’t you the one that always says that there is no such thing as bad sex? So as long as both of these women find someone who loves them, their skill level (or lack thereof) doesn’t matter…right?
    So why suggest the practice?

  6. Emily, the original

    My dearest Adrian,
    Are you not the zombie queen? Doesn’t every male friend eventually fall in love with you
    I’m searching in my initial post for a place in which I imply my male friend wanted to date me. I’m not seeing it.
    My point was … I didn’t think of him romantically, and, for a first time, that was a good thing. Like Evan says in his response to the OP, when you wait a long time to have it, sex becomes a HUGE, WEIGHTED thing. If the OP also has feelings for the guy, sex becomes a even bigger THING. I’m sure her potential partner can feel that pressure. If the situation was reversed and I really liked a man but found out he was a virgin, I wouldn’t want the responsibility. There’d be no way I could live up to his 28 years of fantasy.
    Besides aren’t you the one that always says that there is no such thing as bad sex?
    Yes, but most peoples’ first time isn’t the greatest.

  7. Emily, the original

    Besides aren’t you the one that always says that there is no such thing as bad sex?
    Sorry. I didn’t read what you wrote closely enough. No, I’m the one who’s always saying there IS most definitely bad sex … and mediocre sex and perfunctory sex. I’m the one who says SUPER HOT SEX is rare … unless with the right partner and the right level of sexual compatibility.

  8. Hi Kaci and Malika,
    I guess I am having a hard time understanding: “Why do you feel the need to tell a man who is your “boyfriend” that you are a virgin anyway?”
    Being a virgin is not something to be ashamed of and it is not something that will (in my opinion) affect the relationship in a negative way anyway.
    So do you mind helping me understand why do you feel the need to tell a new guy? Or a become serious boyfriend that you are a virgin?
    …   …   …
    Kaci the few people I have seen and heard of who left a person because they found out that they were a virgin were usually people who felt pressured to make the first time memorable or special; but mostly it was just people who knew that they were not that into you and did not want to be a scumbag and take your virginity for simply a notch on their belt.
    Oh and there are also the people who leave you because of fear! They are afraid that once you start having sex you will want to see who and what else is out there instead of sticking with only them.
    Basically from what I have observed from watching both sides as a third party fly on the wall, at least 2 out of the 3 reasons a person leaves you is because of their own insecurity; it has nothing to do with you, your skill level, or what you won’t know how to do in bed.

  9. It’s better to be a virgin than to do something just because “you don’t want to seem weird.”Would you choose just anyone for a friend? I had a friend once who at the age of 29 slept with some random guy “just because it needed to be done” her words. Well she’s still single at 35. Define what you want. If you want to just have fun, do it. However, if you want to find something more meaningful, why cheapen yourself? Sure you might feel less weird than everyone else but why waste yourself on someone who doesn’t deserve it? You might think “I’ll never have sex” and “if I wait too long, it will never happen.” Maybe. But isn’t it worse to have bad experiences? Why risk getting an STD or having a bad experience for just anyone? Let’s say the guy who is right for you, comes along but because you’ve had bad experiences, you’re closed off or have baggage. Forget the baggage. Wait for the guy who is worth it. There’s always a risk that he’ll never come but… maybe he will. It’s a lot easier to be a virgin if you’re religious. Than you can explain it more… I’m not saying wait for ever if you’re not religious, but maybe wait until you know that you’ve found someone worthy  rather than just accumulate a lot of bad experiences (only because you think it’s better to be that way than to be different)?

  10. I was a 34 year old virgin. Growing up I was abstinent for religious reasons mostly but as I got older it became something I wasn’t going to do for the sake of doing either. I didn’t take an active role in my dating life until I was 30 (up to that point I just figured I would eventually meet someone, somewhere…sounds stupid now lol).
    I just started meeting people and dating using a lot of Evan’s advice and decided early on that if the relationship became serious that I would be open about my virginity but it wasn’t something that needed to be revealed on the first or even third date. I was looking for a committed monogamous relationship before I ever considered sex.
    So that automatically disqualified those guys looking for a good time (most of them were very nice guys but we were just looking for different things in a relationship…we went on a few dates, kissed, but once they realized we weren’t going much further we parted ways amicably)
    I seriously dated 1 guy for 5 months and we fooled around but never “went all the way.”
    I think Evan is right in that as an older virgin we build it up to a big deal. I was ready with this guy but he is actually the one who never pulled the trigger so to speak. I’m not sure if he was nervous about me being a virgin and built it up in his head too or if I just wasn’t giving the right signs….oh well.
    Then 4 years ago I met who is now my husband. All of the awkwardness I felt with the other men I dated, the insecurity regarding being a virgin, not being sure how to proceed wasn’t an issue with him. It just felt right and Evan is right when he says it’s not that big a deal and it’s a fun way to spend some time.
    My advice to you is don’t just have sex to have sex. Date people and have sex when you are in a committed relationship because whether or not you stay with that first guy you want it to be with someone who you care about.

  11. I lost mine at 16 to a long term boyfriend and it was actually a great memory and experience.  But my best friend is a virgin and she is 38.  No religous reason she was just very particular about dating and sort of expects men to chase.  She went to an all girls high school and college.   One thing I see is that while not even realizing it, many people that are virgins are just not so great when it comes to dating or dealing with the opposite sex.  This only applies of course if you want to lose your virginity not if you are waiting for marriage.  In this day and age it’s extremely difficult if not impossible in your late 20s forward to find man that will commit prior to sex yet alone marriage.  And men see virgins are women who will instantly fall in love.   I feel bad for my friend because she’s pushing 40 and has missed out on tons of years of sex.   Sure I’ve had some bad times, but I don’t regret it a bit.

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