How should I tell this guy about my "v" card when I'm in my late 20s?

Okay, so I met this guy online. He's separated and I'm single. We are exchanging emails and all is well but he doesn't know I still have my "V" card. I'm in my late 20s and about to turn 30 soon and most men that I've told have run for the hills when I tell them my "secret". It's to the point that I just want to get it over with but I don't want to be a bad lay either and explain myself. It sucks because he's like my dream guy: successful, attractive, classy, romantic, sensual...and we're already talking about hooking up and I don't want to blow it with my lack of experience like I did so many other times. I need the best advise ever PLEASE!


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Most Helpful Guy

  • If he's really classy, he'll understand that something like virginity is arbitrary.

    If he's really sensual, he'll appreciate that he's the first and only to have touched you this way.

    If he's really romantic, he'll enjoy introducing you to sexuality.

    Any respectable guy would be okay with this. You just gotta talk about it. I think that's what more people need to do, anyway. How many of them just go at it without talking about it first? It's important conversation to have.

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    • TRUE! VERY VERY TRUE!

What Guys Said 10

  • Try the Better Sex video series, and maybe think about preparing? Try to give yourself orgasms, and maybe play with a sex toy or three. Find out how you already like to be touched, and build on that. Women who have multiple orgasms usually can do it because they've given themselves orgasms plenty of times. Learn how to have a clitoral orgasm now, and then later you can experience the vaginal kind.

    As far as the whole hymen issue goes, I don't know if you could take matters into your own hands, but that first time is painful and quite honestly, not extremely fun for a guy - we're basically inflicting pain on you because we're horny. Never feels quite right. I'm not suggesting you break it yourself. But there's always horseback riding.

    On a positive note, after that first time, it gets waaaay better. And if he sticks around that means he gets to teach you everything. Tell him if he's willing to share that first experience with you, he then gets to play Professor Lovetoy for someone who doesn't expect a commitment. You and I know that it's a relationship already, but that's one of the main reasons guys run. They feel obligated to stick around. I got lucky and I already wanted to stick around when I met my virgin girl, and it sounds like he probably does too. It was wonderful after I had to hurt her that first time. I've never really been with someone else so willing to try anything and everything with me. boo hoo, wah...

    The point of the above is, if he's willing to go for it then he's in for a prolonged reward period. I'd think of maybe checking out Dr Joyce Brothers as well, she's pretty savvy and has probably advised other women on this.

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  • There's no reason why he should assume you'll be a "bad lay". If he is a good lover himself he will be patient with you and make sure there is plenty of communication. I'm surprised you've had so many men "run for the hills" over this, I don't see what it is they are running from. I suppose it's possible they want a quickie with no strings attached and figure that you've held onto your virginity this long because you want to marry your first partner. But if you disclosing your virginity weeds out this kind of guy it's probably for the best anyway,

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    • Thanks for the advise but I didn't understand the last part. "But if you disclosing your virginity weeds out this kind of guy it's probably for the best anyway,"...do you mean it's good I waited for someone like this or he'll probably be like the other guys?

    • I don't know the man but it sounds like he's fairly mature and has been in a committed relationship (albeit a failed one) so I doubt he's only looking for casual sex with no strings.

  • It's such a shame that some guys give women crap for being virgins. THERE IS NOTHING WRONG WITH YOU BEING A VIRGIN! If he was a real man, he wouldn't care about it. Furthermore he should be excited that it will be your first time, he can take care of you and make it very memorable for you. Now on telling him, you must and you can't be afraid of the outcome. You said he was your dream man. Isn't your dream man someone you're completely comfortable opening up to and being completely honest with? If he gives you a hard time about it and "runs for the hills" as you said, he is not worth your time and you deserve better. It's a nerve racking situation to be in, I understand but you need to be willing to be open and vulnerable with this man. It's difficult and feels uncomfortable but you need to realize that being a virgin doesn't matter nor does it dictate who you are. OpenClose said it best, he has a great answer.

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  • Don't worry about bringing it up right away. If I was the guy in that scenario, the girl bringing it up & turning it into a big deal is what would make things awkward & weird. Just go with the flow... you can hook up without jumping immediately into sex. If you feel like the situation is getting hot & heavy really quickly you could just let him know in a general way that you're really into him & don't want to rush things in a way that could mess things up. You don't need to make an announcement about having your V card... that can eventually be discussed if/when the relationship develops further.

    In other words, don't overthink it. That will most likely make you stiff & uncomfortable with the overall hook up...and for a guy, that's the worst. Because then it feels like a girl is not 100% into us since she's not comfortable for whatever reason...or worse, that she has some sort of major issues/hang ups. Just go with the flow as much as you can.

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  • you certainly should tell him before sex. On your end, all you have to do to please him is enjoy it yourself. Not as easy as it sounds, actually - especially the first time - but still: make the effort to enjoy it and he certainly will.

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  • Your question is still relevant? Do not despair!

    Those guys who run for the hills when you tell them your secret donĀ“t deserve you!

    Honestly ... as a man I am interested in a virgin of 29 years much more than a 29 year old woman who had 10 lovers. I think it's good that you're one of the few who are really waiting for the right one, no matter how long it takes.

    A 29 year old virgin is really rare, the man who comes together with you should be lucky, he has a very valuable treasure.

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  • being a virgin doesn't bother me in the least. in fact, it's quite sexy that you'd think I'm special enough to lose it to. -- in fact, make sure he is the one you'd like to lose it to!

    when going for it, just take a second, say that you're a virgin and ask him to be gentle -- or have a chat beforehand. what's the worst that can happen? if he freaks out, he wasn't worth giving it to!

    anyone that loves you will be considerate and thoughtful!

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  • your a virgin in your late 20s wow... but if you thinking about hooking up you shouldnt

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    • Why is that so crazy?

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    • Well for starters, nothing happened yet to lead to relationship...we've just started talking and haven't even met each other yet. For all I know, this could be over tomorrow. I'm just talking about what to do if the situation of sex was to occur and wanted advise on that.

    • you waiting for the right guy or something

  • Ho ho ho good luck :)

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  • I really really hope you don't get this guy because the 1st thing you mentioned about him was being successful over the rest. Which means your #1 preference is the guy's money. Either way I can't expect anything less from a girl.

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What Girls Said 4

  • If I were you, I would get to know him. And then when you're together at home, maybe on the sofa relaxing or something like that, tell me.

    Just say to him you've never met someone you've really wanted to give it to, or that you want to wait till you're married, whatever your reason is, just tell him.

    I've seen some people on this website who still haven't kissed anyone so I wouldn't be too upset. And hey, he might even find it cute.

    If it's meant to be, it will be, and it sounds like you're pretty into this man. Sex isn't everything, I doubt he's expecting you to be a p*rnstar in bed.

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  • Not sure if this is the 'best advice ever' but maybe you shouldn't tell him at all. He doesn't need to know and you can easily play off all ahem, evidence, as something else.

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  • If you want something long term with this guy, you should tell him. Don't overwhelm him with it by making a big deal out of it. But you're going to feel a bit stressed about having sex for the first time ... let him know so he can understand your emotions and behaviors. Sex can be kind of unpleasant physically the first dozen times or so -- a guy is going to pick up on your body language that you're not as into it as he is. He may think it is something he is doing wrong.

    A guy who actually cares about you is going to want to feel like you trust him. Good guys DO want to feel like good men, but we have to make it easy on them by a) being responsible for our own emotions/behaviors 2) being honest and not trying to manipulate them into getting our desired outcome 3) giving them a chance to be good.

    Chances are, the guys who "ran for the hills" were after quick sex. That happens. But a guy who wants a real relationship will be patient.

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  • Just say you haven't been with anyone before in that way? I don't think you have to say anything else unless he asks. Just because you haven't done it before doesn't mean you'll be bad at it. Since you're a girl I would think you have a lot more emotions to help you along with it really. :P

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