Miss Information: Advice for a 25-year-old virgin

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Dear Miss Information,

I’ve been seeing my friend-with-benefits for over three years. In that time, I’ve been on one date with someone else, and my FWB hasn’t dated anyone at all. This is not by contract we’ve both agreed we’re welcome to see other people.

I’m starting to crush on my FWB big time, and I know that he’s crushing on me too. The problem is the age difference. He’s twenty-six and I’m forty. He’s also very good looking and personable. No matter how he feels about me now, I know it’s a matter of time before he finds someone else, and I don’t want to interfere with his happiness when that happens. But I also don’t want it to break my heart.  I’ve been thinking that maybe I should start dating in order to prepare myself for this eventuality and keep from focusing on my FWB as "The One." But I think that despite our stated agreement to keep the relationship open, my FWB will probably be hurt by my doing so.

Should I just stay with him, and stock up on cheap wine and Häagen-Dazs to prepare for the inevitable? Or should I protect myself by dating others, possibly leading to an earlier demise for the relationship? — Confused Cougar

Dear Confused Cougar,

Forty is not that ancient and twenty-six is not that infantile. Just as there are lovelorn women who prefer Anchor Steam and olives to Franzia and rum raisin, there are youngish men who are capable of mature, committed partnerships. It’s not about sex or fetishes or biding your time until something better comes along. It’s also not a hunt for a sugar mommy to lavish you with economy-sized boxes of cereal and tube socks. These are regular guys who fall for someone a little older. That’s not a tenth of what it’ll take to get you on Jerry Springer. It will, however, give birth to zillions of newspaper trend pieces, a Jennifer Aniston flick, a Courteney Cox series, and a throwaway reality show.

While we wait for "The Manther" to get the green light from ABC and Columbia, let me ask you: how many of these concerns are valid and how many come from this bullshit soufflé of internalized media messages, low self-esteem, and personal prejudices that you’ve whipped up for yourself? Just because someone tells you to feel like an oddity doesn’t mean you have to. Think about it:

Fact #1: Whether it’s intentional or not, you’ve been exclusive for three years.

Fact #2: You’re feeling something for him and you think he’s feeling something similar.

Fact #3: "Good looking and personable" people look for the same in others.

So why are you the charity case? Why not him, who came of age when Ricky Martin, Britney Spears, and Sugar Ray were topping the charts instead of Prince, Madonna, and Stevie Wonder? You’ve got the experience, street cred, and the good looks to attract the young’uns, not to mention what I’m assuming is a much healthier bank account. Will he be doing as well at your age? Who knows.

If you like him, put it out there. If he’s not into it, you can go back to the previous arrangement or find someone new and get rid of this dark cloud. You don’t have to send him a dozen orchids or prepare a big speech. Make a joke about "renegotiating your contract" or ask a rhetorical question ("Why do you think after all this time we haven’t ‘gone there’ as boyfriend and girlfriend?") to get the conversation going. And a little liquid courage couldn’t hurt.

Dear Miss Information,

I’m a twenty-five-year-old straight male and regrettably still a virgin. I just never really seemed to hit my stride with girls in college, and next thing I knew I was out in the working world with no idea how to meet anyone.  I’ve started to get it together recently though, and I met an amazing girl.  We’ve really hit it off and it seems extremely likely that clothes will be coming off in the near future.

My question is this: when the time comes, should I tell her I’m a virgin or stick with the fake-it-till-you-make-it plan? On the one hand, it would be kind of a nice pressure release to tell the truth, but on the other, I keep picturing her thinking, "He’s still a virgin!? I wonder what’s wrong with him?" For my part, after many hours of reading advice columns and articles, I’ve culled together a plan that I believe to be a fairly solid stab at what sex should be like: a steady build up of rubbing/kissing/licking various body parts leading into some (I can only imagine glorious) oral action. I’m not sure exactly when to transition to actual intercourse, but when we get there I’ll just try to keep an even thrusting tempo and hold out as long as I can. I think I can pull it off.

I would of course prefer not to have to follow a strict plan and just have her tell me what to do, but then I would have to admit that I have exactly zero first-hand knowledge of what turns a woman on. I’d welcome any advice you might be able to proffer. — Inexperienced, But Eager To Please

Dear Inexperienced,

Virginity is not a sexually transmitted disease, nor is it a secret wife or a girlfriend. There are benefits to disclosure, both for the person you’re sleeping with and for yourself, but it’s not a moral obligation. If I’m reading your letter correctly, this virginity is an unfortunate product of circumstances, not some deeply held personal creed or prerequisite to finding a spouse. In either of those instances, there’s more of an impetus to be up-front. However, it’s totally acceptable to play your V-card closer to your chest if having a new experience and popping your cherry are the primary goals. In short, do what makes you comfortable. You may opt not to tell her, then have it come up mid-coitus. You may tell her right afterwards or a month later during a TV commercial.

Which leads me to another point I want to impress upon you, Inexperienced: sex is unpredictable. It’s great that you’re studying up. The internet, books, and magazines can be a great way to learn, and so is talking to people you trust. But I don’t know about all this, "I’m going to do this, then that, then this, then more of that…" Are you engaging in a natural, organic act or blocking out stage directions for a Broadway show? I think your second instinct, i.e. can it with the fancy plans and follow her lead, is going to work out much better for you. And while everything you mentioned sounds lovely, keep in mind she’s also going to want to pleasure you as well. Half the fun is the power dynamic and knowing you can get the other person off.

As far as the transition to intercourse, I wish I could tell you that balloons will fall from the ceiling, a disco ball will appear, and a guy in a sequined tuxedo will yell, "And awaaaaaaaaaaaaaaaaay we go!" The reality is more like: "You ready?" "Yeah," followed by the donning of a condom. If that feels too direct, something like, "I’m really turned on," or, "I can’t wait to be inside you," usually gets the message across, as does, "Should I put this on?" while holding up a condom.

Readers, any additional advice for Inexperienced? What didn’t you know then that you’re happy you know now?

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