The Almost-30-Year-Old Virgin

Please watch your mouth with today's letter. Don't get your comment poofed away.

Hi Meredith,

I grew up in a pretty conservative home and went to a religious college where sex wasn't unheard of, but there was no stigma for those who were not doing it. I kind of drifted away from the faith in college, but still didn't really date much. There were a couple girls, and I made my first grilled cheese sandwiches then, but never went all the way.

Since I left college I've had one long term girlfriend, but not anyone I really saw a future with. I've been waiting until I was married but always thought I would be married by this point. Now I am staring my 30th birthday in the face and feeling a bit like a movie should be made about me starring Steve Carell.

I'm not an Abercrombie model by any means, but I've had plenty of opportunities. My question for you is whether or not I should just take one. I'm not religious anymore, and it doesn't look like I'm going to get married any time soon. There's really no good reason not to have sex except that I've waited this long and I figure I might as well see it through.

Obviously that has been good enough for me so far, but I'm getting to the point where I am worried that not only am I going to a 30-year-old virgin, but a 50 or 70-year-old one. That was never part of the plan.

So what do you think?

– The Almost-30-Year-Old Virgin, Boston

It's never going to feel just right, TA3YOV. If you wait until you're married, it'll be weird. You'll wonder if you should have tried it with others. And if you try it with people you don't wind up marrying, you'll wonder if you should have waited.

My advice is to try it with someone you like enough -- someone with just a little bit of potential. Because my concern is that you're not connecting with the women you date because you're not really allowing yourself to be vulnerable with them. We talk a lot about emotional intimacy on Love Letters, but physical intimacy is another way we get to know people. It's certainly another way we get to know ourselves.

So yeah, try it. Not with just anybody, but somebody nice. Somebody you want to get to know better. And expect that you'll second guess the whole thing -- because you will no matter what. But also expect to learn something about who you are, what you want, and what it's like to do something scary with someone else.

Readers? Should he just wait at this point? Is there a reason he's holding out besides his religious past? Thoughts on physical intimacy helping with emotional intimacy? Stay G-rated.

– Meredith