Dear Wendy
Dear Wendy

His Take: “Should I Tell The Next Guy I Date That I’m A Virgin?”

“I’m 23 and a virgin. I was raised in a pretty conservative home and I’ve always viewed sex as something I want to share with someone I’m serious with. Well, I haven’t met that person yet and I’m getting anxious to just do it and get it over with already. I decided that the next guy I go out with is going to be the one — as long as I like him, of course. Do you think I should tell him I’m a virgin or will that just scare him off? — Virgin




DENNIS: Well, in that case… hello, my name is Dennis, and my phone number is 555-6969… But seriously, I’d like to suggest a minor change to your plan: instead of deciding that the next guy you date — and like — is going to be the one, how about deciding that if the next guy you date — and like — turns serious enough, then he’ll be the one?

If you’re so set on losing your virginity to the next guy you go out with, don’t you think you might become just a bit too eager and end up regretting your decision? You’ve waited 23 years. Why rush at this point? To answer the question, though: yes, I think you should tell him. But, definitely don’t tell him that the next guy is going to be the one. Because then you’re just opening yourself up to get screwed over (pun intended). Just tell him that you’re ready to lose your virginity… to the right guy. Good luck!

ANDREW: You probably don’t want to tell him on the first date but, when it’s time, it might make for a better and more intimate experience if you do tell him. Whether or not it will “freak him out” there’s really no way of knowing… UNLESS YOU SLEEP WITH ANOTHER VIRGIN! Do it! Grab that nice shy guy you only think of a as a friend and get naked with him! Let’s be honest, your first time will more than likely be a disappointment anyway, so your best shot at uninhibited exciting sex is gonna be with a guy in the same virginal boat as you. It probably won’t be good sex but I bet it’ll be a fun and shame free. That makes for a pretty good first time.

DAVE: First off… congratulations. The only thing I respect more than a 23-year old virgin is a 24-year old virgin. (Granted, it gets creepy once you get into your 30’s). The fact that you have been able to maintain your virtue for so long only punctuates how important it must really be for you to share it with just the right person. You are in a situation now where you need to RAISE the bar, not lower it. Seek out a mate who shares your values — someone who is worthy of you. Think how wonderful it would be if he was a virgin too, and how you could do things at your own pace as you set out on your committed relationship. Plus… no fear of social diseases!

You do not HAVE TO wait until you get married, but at the very least wait until you fall in love with someone that you’d like to marry, and who feels the same about you. In that way, sex doesn’t become that big “be all, end all” in the relationship; it takes its rightful place as just one of the many wonderful shared experiences in a long term relationship.

* If you’d like to ask the guys a question, simply email me at [email protected] with “His Take” in the subject line and I’ll pass your question along to them.

41 comments… add one
  • avatar

    sarolabelle March 3, 2011, 12:09 pm

    My boyfriend and I are both 29 and virgins…and waiting. It’s not that unheard of. Embrace it!

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      Amanda March 4, 2011, 11:12 am

      I am proud (and I don’t even know you)!!
      I wish I would have waited till I was older. I am only 22 but when I lost it at 15 I immeditately regretted it. It wasn’t bad, it wasn’t horrible or embarrassing. I just realized too late that I didn’t do it for anymore reasons than all my girlfriends had already done the deed. Maybe it’s because I was never talked to about sex as a child or tween and was curious as well as being peer-pressured but I did it anyways and wish I could take it back. Even if I would have waited till I was 17 and with the boyfriend I am now engaged to that would have been better I think.

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    RoyalEagle0408 March 3, 2011, 12:20 pm

    As a 25 year old virgin, I get that it’s difficult to know when to tell the guy. I’m pretty upfront about it (especially when alcohol is involved), but I tend to date guys I’m already friends with who know ahead of time that I’m not going to sleep with them.

    Wait until you’re sure you’re ready and that if things go south with the guy, you won’t regret it. If you’re so sure that you want to lose it to the next guy you date, it sounds more like you just want to have sex. If I were you I’d re-evaluate why you’re still a virgin, how much being a virgin means to you and how long you’re willing to remain a virgin. I totally understand the anxiety as well, which is why I think you really need to think about what _you_ want. Not what your parents or anyone else wants or expects. If you’re just looking for a meaningful experience for your first time, a close friend might fit the bill. If, however, you’re looking to be a one and done type girl, don’t assume the next guy you date will be the guy that you end up with. And if you’re looking for something in between (a meaningful experience with a guy who has the potential to be someone you spend the rest of your life with), I think you should definitely wait until you’re sure of your feelings.

    In the end, it’s your decision. And no one else’s.

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    • avatar

      maynard March 3, 2011, 12:52 pm

      great advice!

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        RoyalEagle0408 March 3, 2011, 1:16 pm

        Thanks! I have to admit that it’s advice I got from a few close male friends about my situation when I was having a bit of a life crisis about my virginity.

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    ReginaRey March 3, 2011, 12:23 pm

    If you’ve always viewed sex as something serious that you want to share with someone who you really care for, then do that! If that is the standard you have upheld your whole life, I think you may regret giving it away to the next guy who walks into your life. I think Dave is especially right – you don’t need to be lowering the bar because you’re anxious to “get it over with.” Please don’t throw it away on the next guy you sort-of-like just because you don’t want to be 23 and a virgin…I think given what you’ve written, it will be much more special and fulfilling if you wait for someone you truly care for.

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    • avatar

      Spark March 4, 2011, 7:31 am

      I totally agree. If you’ve always thought of sex as special and the territory of a serious relationship, I think you are going to be in for a HUGE emotional shock when you give it away. That’s not how you’re wired. It’s something you’ve placed a premium on for your whole life–don’t throw it away or make it cheap on a whim.

      I lost my virginity at 20 to my first serious boyfriend. I’d always valued sex, and I thought I was ready to have the intimacy with someone. As it turned out, even though I loved him and truly wanted to be intimate, and waited for the right time (after seven months of dating), and thought I was ready, it was STILL an emotional shock that left me a little anxious and uncomfortable with what I’d done. And I had NO DOUBTS that I was 1000% ready. To me, it doesn’t sound like you even THINK you’re somewhat ready.

      Just don’t do it. Wait for a special guy, fall in love or get where you in your heart know you need to get, and let things happen naturally. There may always be a tiny bit of anxiety, but it there won’t be the fallout that would happen if you did it with a stranger just cause.

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  • avatar

    TheGirl March 3, 2011, 1:06 pm

    I have to agree with the guys here – don’t just do it with the next creepster you see. You will regret it! You’ve waited this long, you should make sure it is at least a memorable and positive experience, and the only way to do that is to be with someone that you care about, who knows you are a virgin (you don’t want them trying to bring in any kinky stuff your first time or rushing things) and who you know will respect you. I like the finding another virgin idea, but I think it might be difficult to do. Most guys that are still virgins at 23 do not advertise it and often lie about it.

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  • avatar

    Margblogger March 3, 2011, 1:18 pm

    How refreshing to hear the men give this advice. Sometimes I lose faith in men and their responses to situations like this, but you guys gave some wonderful advice!

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      RoyalEagle0408 March 3, 2011, 1:21 pm

      These are special guys. 🙂

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      • Chicago-Dude

        Rahmtown_Dan March 3, 2011, 1:28 pm

        Agreed. The lot is fercockt!

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        _jsw_ March 3, 2011, 1:32 pm

        Actually, if I’m counting correctly, I believe they’re threecockt.

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        Dennis Hong March 3, 2011, 2:13 pm

        Special? Or thpecial?

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        bubbacatz March 4, 2011, 8:54 am

        I think they are just normal guys – they really do exist.

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    Lindsay March 3, 2011, 1:26 pm

    My first thought was also: If you’ve waited this long, why rush it? There’s no guarantee you won’t regret who it’s with or that it won’t be a disappointment, but you still have the opportunity to make your first time into something special.

    I lost my virginity at 22. I sort of had the same mind-set. Not that I’d definitely do it with the next guy, but I figured that the next guy I started dating I’d probably do it with, and I did. It’s not a regret, but I’m not particularly pleased with who it was with, and it wasn’t special at all. Granted, had I waited until I was seriously in love, I would still be a virgin (I’m 24), so I get where you’re coming from. But losing your virginity isn’t something that suddenly makes life better or makes you feel more adult. It’s not worth doing something special with someone who isn’t special.

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      MissDre March 3, 2011, 1:33 pm

      I lost my virginity to a friend, cuz I was feeling insecure about the only person I knew who was still a virgin. I don’t look back and regret it, but if I could go back and change it I would. It didn’t mean anything, it wasn’t special at all and it was definitely disappointing. I wish I had waited at least until I was in a committed relationship… at least if I had, maybe I would have taken sex more seriously and I could have saved myself a lot of heartache.

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        MissDre March 3, 2011, 1:33 pm

        about being*

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  • Chicago-Dude

    Rahmtown_Dan March 3, 2011, 1:30 pm

    I’m with the fellas on this one, though I disagree a 30-yr old yenta is “creepy”.
    40s… yea but even that, Dan-don’t-judge.

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  • parton_doll

    parton_doll March 3, 2011, 1:35 pm

    Not that you have to, but there really is no issue with waiting until you are married either. Again I am NOT saying that you have to, but it is okay if you decide to do that in the end. I waited until I got married at 25. Since the first time was awkward, I personally am glad it was with my husband. But of course, please do what’s best for you. I think the guys above gave great advice. I just wanted to jump in with the waiting point of view in case you want to revisit it 🙂

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  • avatar

    joy March 3, 2011, 1:40 pm

    When I met my husband, he was 35 and still a virgin. No he did not live at home with his parents nor was he weird or whatever. I actually was surprised when he told me he was a virgin. I asked him why, and he said he hadn’t met the right person until he met me. He did tell me before we ever had sex. It wasn’t weird though I know he had reservations about how he would do. He did just fine, and I have to say we have 2 beautiful boys now! No, I wasn’t a virgin and lost mine pretty much the first year of college. Did I regret it? Somewhat. But I did love my boyfriend at the time and he did become my fiance for awhile but it didn’t work out. I definitely think you should not rush into something like losing your virginity until you are ready. At that time I’m sure you will feel confident enough to tell that special person who will, no doubt, make you feel special.

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    _jsw_ March 3, 2011, 1:41 pm

    My advice is this: don’t have sex until you feel you’re ready for it and until you’re with someone you with whom want to have sex, then have sex. It’s that simple.

    No one aside from you yourself is going to judge you on how you lost your virginity except for those who will always judge you unless it’s on your wedding night.

    No other guy is going to care how close and special to you the first guy was because, honestly, we really don’t want to know about him. Likewise, we don’t care to know if he was some one night stand. We just… don’t want to know.

    Nothing you do will guarantee the first time and first person will go as you planned/expect, and in fact it likely won’t, one way or another. Losing your virginity probably won’t be utterly amazing and similarly probably won’t be utterly disappointing (although the latter is more likely). Odds are it might be a bit uncomfortable – as much because of your nervousness as anything – but that it will improve rapidly as you keep at it, and some people enjoy it right from the start.

    The important thing to remember is that virginity, and losing it, is as significant as you make it out to be, no more and no less. You won’t be a different person the next day regardless of whether or not you had sex the day before. You’ll just lose a label.

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    • avatar

      Dennis Hong March 3, 2011, 2:15 pm

      Ahem. Why are you giving your advice here? Was your advice featured on this one? Was it? Was it? Do you see your pretty little mug up there? Do ya? Do ya, punk?

      Ummm… no, I don’t think so. *waves fingers*

      :-p

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        _jsw_ March 3, 2011, 2:25 pm

        I understand that you feel intimidated by my advice, Dennis, and I truly hope that you can learn to accept that the fact that just because my advice is worded differently doesn’t make yours wrong. I mean, lots of other things could make it wrong, but just not solely because you used different words in a different order. Or, you know, just because started off by hitting on her. 😀

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        _jsw_ March 3, 2011, 2:29 pm

        I hope people realize I’m kidding. Dennis (and the others!) gives excellent advice, and the fact that he starts it off with a phone number is not to be seen as a negative. I know for a fact that he buys a new burner phone for each advice piece he writes and that he uses a labeler to note the writer’s name and issue on each phone. That way, when they call that specific number (and they do, for whatever reason, always call him), he’s able to refresh his memory on who they are. He is also a very craft-y person and has tailored one of those behind-the-bathroom-closet-door organizer thingies into his jackets to hold all the phones.

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        Dennis Hong March 3, 2011, 2:35 pm

        Well, sure. But I only do that because I don’t know how to tap someone’s phone.

        Don’t think I’ve forgotten about that one!!! 😉

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    • avatar

      Margblogger March 3, 2011, 2:17 pm

      Excellent advice, as always.

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    ArtsyGirly March 3, 2011, 2:17 pm

    LW – I totally agree with most of the commentators above. Don’t push yourself into sex before you are ready just because you want to loose your virginity. My one point of dissension is with people who are telling you to sleep with another virgin. If you end up dating and having strong feelings for someone who is a virgin so be it, but the same goes for someone who has a sexual past.

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      Red_Lady March 3, 2011, 11:59 pm

      That was the one thing I wasn’t too keen on either. I was also a 23 y/o virgin, and lost it to someone who wasn’t a virgin, which actually made me feel good ‘cuz he knew what he was doing. But LW, it really doesn’t matter if he’s a virgin or not – as long as you feel comfortable with him (and know he’s disease-free!). Congratulations on having standards so far – I hope you find someone worth having sex with for the first time soon.

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        Golden_Key March 4, 2011, 8:59 am

        “it really doesn’t matter if he’s a virgin or not – as long as you feel comfortable with him (and know he’s disease-free!)”
        THIS.
        I was a 22 year old virgin until recently, and I think this is great advice. My first time happened to be with another virgin, but that didn’t necessarily make it better or worse. It was much more important that I was comfortable and trusted him. For me, trust was the biggest prerequisite–it made me relax a lot more, and considering my own first time was quite painful, it was good to feel cared for and safe. Plus, to be honest, sex is awkward and kind of funny. It’s nice for a first time to be with someone who you can laugh with if something goes “wrong” or even just different than expected.
        So LW, make sure that you are not just ready to have sex, but that you are ready to have sex with a specific person. He doesn’t have to be the love of your life, or even someone you’re in a relationship with, as long as you trust him, are safe, and feel very comfortable with him. Good luck!

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    LennyBee March 3, 2011, 2:17 pm

    I was in the same boat as the LW at 23, and thought I wanted the same thing – to just get it over with. But, that decision comes with anxiety as well, and in the end, I just avoided dating until I found the right man 3 years later. Turned out, the “right man” shared my values, and was also a virgin. We waitetd a year into our relaionship to have sex, and although it was awkward, and frankly, a little painful, there was no anxiety, no stress, and no regrets.

    So, my advice is to relax, and wait for the right person. Odds are the right person will share your values. Also, first-time sex is not as easy as sex the n-th time. It will likely go much more smoothly if you tell your partner you’re a virgin beforehand. Besides, do you really want to lose your virginity to a guy who’d be scared off by that fact? If he’s scared off beforehand, wouldn’t he be scared off if he figured it out afterwards?

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  • fast eddie

    fast eddie March 3, 2011, 3:25 pm

    Losing your virginity is something you can only do once and there’s no way to predict if it will be a positive experience. Obviously your intelligent and have thought it through. Do yourself a favor and make it as special as possible and not have any regret afterward.

    One of my young friends and his GF didn’t go all the way until he put an engagement ring on her finger after being a couple for 6 years. According to him they did everything else for a couple of years and they aren’t telling how the big event went (they’re married now) but I’m willing to bet it was special for both of them.

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  • avatar

    Painted_lady March 3, 2011, 3:43 pm

    My $.02 for what it’s worth: I grew up thinking I was going to wait until marriage, and as I got older, I realized that wasn’t what I wanted anymore. Naturally, I didn’t want it to just be some random dude, and yet, I got so worked up about whether or not I was going to sleep with, you know, every guy that crossed my path, that for those couple of years in college where I was actively trying to lose my v-card, all my relationships were so stressful and fraught and therefore ineffective at losing it.
    When it did happen (at 23, oddly enough), it ended up being the most natural thing in the world, and yet completely ironic. An ex I still cared for came into town, and we got really drunk and…you know how it goes. It was simultaneously completely sleazy and hilarious and yet sort of sweet and wonderful. It wasn’t someone I thought I was going to marry. It wasn’t someone I was in a relationship with. It wasn’t even really someone I loved. It was a relief, though. And it was still significant. I actually wish I hadn’t blown it up so huge previously, because it became a massive focal point that ended up crippling what could have been some really great relationships.

    And also, while it was a significant experience for me, it wasn’t the most significant one I’ve ever had. And it doesn’t discount any of the ones that followed. My boyfriend now told me once he wishes I’d been his first, but I’m glad he wasn’t mine – I’d much prefer it if he’s my last.

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      Painted_lady March 3, 2011, 10:50 pm

      So sorry, I got so wrapped up in my own story, I forgot my advice: do this on your terms. The experience is significant enough that it will be whatever you make of it. I was lucky enough that my first time was with someone who knew I was a virgin, but I had a couple of close calls with guys who were cool enough that when I broke the news – after a few weeks to a month of dating – they were both understanding that I was skittish and at the same time not freaked out by that kind of pressure. One was actually a friend with (fringe) benefits, and he was absolutely a doll about the fact that I panicked twice at the last possible moment. While the stereotype is that guys are all sex fiends who just want into your pants, my small sampling speaks incredibly well for men in general. So, you know, trust your instincts, but also don’t overthink it. While it is incredibly meaningful in the moment, it doesn’t have to define who you are sexually for the rest of your life. I hope there’s an update soon!

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  • avatar

    Anna March 3, 2011, 5:39 pm

    So my sister is a 37 year old virgin…always thought it was sad but never considered that it might be creepy. I lost it at 19…couldn’t wait anymore.

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    thyme March 3, 2011, 7:07 pm

    I have a friend who did exactly what the LW is planning. She lost her virginity at 24 when she decided she just wanted to lose it to the next guy she dated, “as long as he’s not an ass.” Well, we she told Mediocre Next Guy that she was ready, he waxed poetic about how honored he felt that she chose him to be her first after waiting so long, and she, being the romantic that she is, replied, “I am just ready to lose my v-card, and you’re not an ass.” She did sleep with him, and she found it very painful and remarkably unimpressive. They broke up shortly thereafter.

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  • avatar

    PinkPanther March 3, 2011, 7:28 pm

    I was 21 the first time I had sex and hadn’t even been thinking about it at that point. I started dating a guy who was so wonderful that I couldn’t imagine it not being him. He knew that I was a virgin and after I had decided I was ready, he waited yet another month until I had been through my first month on the pill. One night we we had been drinking, and it could have happened then, but I told him that I didn’t want either of us to be drunk the first time. When things finally did happen, he was so great about it being my first time. I think it was about as good as a first time could be. I advocate waiting until you have found someone who is special to you and telling him that you are a virgin. I think the first time would have been quite a bit different if he hadn’t known (I was not the first for him). We’ve been together almost five years now and I’m so glad that I waited until I was with him.

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  • avatar

    Jennifer March 4, 2011, 9:12 am

    I was 23 when I lost my virginity and it was not with anyone special. In my case, I was not overly religious and had not “saved” myself consciously. I had remained a virgin because I wanted to at least lose it with a BF and, admitedly, was scared it would hurt. I never really dated anyone or had an official BF. So when I was 23 and still a virgin, panic was setting in. Almost all my closest friends had lost it or were engaged and waiting. It started becoming a burden. A symbol of my unattractiveness, in my twisted head. I didn’t set out to lose my virginity the way that I did and afterwards I was very emotionally conflicted. I was sad about who, where, and how it happened. But elated about having shed that burden. Looking back I don’t regret losing my virginity. It could have been better or worse. What I regret is putting so much value on it and being afraid of whether or not it would hurt. So much anxiety and self-flagellation over sex for no reason. Everyone is different. But I will admit it would have made the emotional part of losing my virginity easier, if it had been with someone I loved. Either way I’m glad to be rid of it.

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  • avatar

    demoiselle March 4, 2011, 9:40 am

    I understand how the letter writer feels. It isn’t that uncommon to still be a virgin in your early twenties, though. I was 23. I have another friend who was 27. I’d recommend waiting until you find someone you really like and trust, and whom you know well enough to judge whether he is someone who is caring. Do tell him–and not just the moment before intercourse. I warned my boyfriend very early on (because I had never done more than kiss), and it gave him time to figure out whether he could handle being my first. It also gave him time to think up something special, and to–frankly–ask advice about how to do it right so it wasn’t painful or unpleasant. He’d had a very bad first time, and was invested in making sure mine was better. It was, in fact, a very good experience. And perhaps that is the best thing that came out of that relationship!

    I see some posters are recommending finding a virgin on purpose. Although if the guy you like is a virgin, I wouldn’t write him off, first time sex is an awkward and sometimes nerve wracking experience. It helps to be with someone who has some experience. I was someone’s first, too. In both cases, I was glad that one partner had had sex before.

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    anna728 March 6, 2011, 8:57 pm

    I could never really relate to all the stuff about wanting the first time to be special. I lost it at 15, really drunk, to a friend of mine. Not an especially close friend, but he was cute, although kind of a man whore. It was not planned, and it was not with anyone I loved or was even dating, but I never regretted it (almost 6 years later). I don’t think losing your virginity is very romantic, unless clumsy and awkward is romantic to you. Obviously someone who does have those feelings about virginity should act accordingly, but for others just doing it can get rid of the pressure of worrying about things like in the letter.

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  • avatar

    MeghanSara March 7, 2011, 6:14 pm

    WAIT! Don’t do it. I didn’t lose my virginity till I was 22 and THAT was after a year and a half of a serious, committed relationship. If you want to wait for someone special, for the love of all that is fluffy, wait for someone special. As much as you want to “get this over with” now, someday down the line, you may “regret the way you lost your v-card”.

    I know there’s a stigma against waiting too long to have sex (Thanks, DAVE, for insinuating that 30-year-old virgins are “SAD”), but the only person who should decide what’s normal is YOU. I wish I had waited longer, myself, having had sex for all the wrong reasons – my “serious boyfriend” at the time convinced me that if I really loved him, I would do it; that being exclusive to one another meant we should be having sex, that he had already waited long enough. It was very painful and traumatic and scarred me for quite some time and led me to not respect myself, become promiscuous and make a lot of bad decisions.

    I wish you’d think this through.

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  • avatar

    Kristina March 10, 2011, 9:51 am

    I lost my virginity at 25. It just happened as the next natural thing to do and I had not been interested in losing it or in saving it. It just happened. But I’m glad I waited. I was ready for the emotional, physical, and financial ramifications of sleeping with someone. It was with a man who was super sweet and made my first time as wonderful as physically possible. I trusted him and loved him 100%, and have never regretted or doubted my decision for a second. It’s worth waiting for, trust me. Have more respect for your body and heart. Give them the best treatment.

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