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Yesterday we answered a thirty-something virgin’s plea for help. Today, we tell her and this woman and virgins everywhere whether they should tell the first guy they’re going to have intercourse with that they’re still carrying their V-cards:

Dear Em & Lo,

Do I have to tell a guy I’m hoping to do it with that I’m a virgin?

–Sandra Dee

Dear S.D.,

Yes and No.

Here are the conditions that require a “Yes” answer to the above question (more than one may apply, but only one is neccessary for a “Yes”):

• If you’re hoping to have a relationship with this guy. You want to try to build a good relationship with this person? Then you should be open and honest about your situation — that’s what good relationships are built on, openness and honesty! And if he feels the same way about you, he’ll want to know.
• If you want to make sure you’re having sex with a man who would not consider virginity a deal breaker. Telling him is a way to weed out anyone who doesn’t want to take the time to make it special, can’t handle the pressure, is afraid you’ll fall too hard for him, etc. But don’t worry, not every guy feels this way, so you won’t be a virgin forever — there are plenty of men out there who will be over the moon to discover you’ve never done it before… because you’ll have no one to compare him to!
• If you want the experience to be as good as it can be. You’re going to have a lot of sex in the years to come, both good and crappy, but you’re only going to lose your virginity once. So why not try to make it special? We can’t guarantee that the earth is going to move for you the first time — in fact, for women, the first time is rarely orgasmic, and it’s often downright crappy. But that doesn’t mean that you shouldn’t even try to make it a bit special. If a guy knows it’s your first time, then he’ll be able to help you celebrate the occasion by going very slowly, paying extra special attention to the niceties like soft lighting and good music (so that you won’t have to remember for the rest of your life that you did it the first time with NPR’s “Fresh Air” playing playing in the background), and basically just being uber-attentive to your responses. (In an ideal world, your first time with any new partner should be like this, but damn it, we don’t live in that kind of world!)
• If he flat-out asks you. We can, under the right circumstances, condone a little reticence on the topic of your virginity, but outright lying in bed is for losers who don’t like orgasms.

Here are the conditions that might warrant a “No” answer (all of them should probably apply before deciding not to tell him):

• If you don’t care whether you see this guy again. If you see this as a one-night-stand kind of thing, with not a lot of emotion invested in it, then we guess you could just not mention it.
• If you just want to get it over with as fast as possible. If you don’t want to build it up too much, if you want to take some of the pressure off, if you want to be in the moment and not complicate things, then you might not bring it up.
• If you’re afraid the news of your virginity will scare him away. We’re not going to lie: Some guys won’t want to take your V-card. That’s a lot of pressure on a guy — for example, if he’s just thinking of this as a casual fling, then he may not want to be your first, as he might worry that you’ll get too attached. Probably not the most sensitive type of person to lose your virginity to, but maybe that doesn’t matter to you at this point.

If it’s not glaringly obvious, we strongly favor the “Yes” answer to this question. We think you owe it to yourself  — and to the guy — to fess up. Regret is possible with either approach, but we think your odds of big regret are greater by not telling him.

Whether you decide to tell or not, before you do it, do yourself a favor and read a good book about sex. Like, oh, perhaps our book Sex: How to Do Everything, to pick one totally at random. Seriously, though, a book like this will teach you the way around your own body, it will help you discover the various routes to your happy place, and it will give you a few ideas of what to ask for when you do find the right man. Because you should never expect any man to have all the answers when it comes to your orgasm.

Have fun storming the castle!

Em & Lo

MORE LIKE THIS FROM EMandLO.com:

• Dear Em & Lo, I’m a Thirty-Something Virgin – Help!
• Dear Em & Lo, How Far Should I Go to Keep a Guy?
• Confession: Losing Your Virginity Ain’t No Big Thang
• The Virgin Diaries