My Girlfriend Wants to Get More Sexual “Experience” Before Getting Engaged. What Should I Do?

I’ve been dating this girl for two and a half years now – not just dating, but living with, I think that makes it all the more serious.   We were good friends for a year before all this, which is why we were comfortable with starting dating and living together at the same time…   The problem, I think, is that while I was her first, I had prior sexual experience with former girlfriends.   Maybe it’s my fault, for wanting to broaden her mind, but now she’s assured me she’s going to have sex with another man, no one in particular, but just because she wants to have a certain level of experience before she commits.  

Last summer, we had a “break”, some time apart, and I know she’s been with another guy, though just oral sex.   Even though this devastated me, I agreed to get back together – she says she’s glad to have had time to figure things out, and in a sense, so am I.   But now I’ve become more insecure about all this, and certainly this jealousy is putting a strain on our relationship.   My problem is, she’s sure she’s going to sleep with another man, and that she doesn’t want to commit until she’s had “adequate” experience with sex and men; on the other hand at the moment we really are in love, and really enjoy being together – we can both imagine a long-term future together. Am I just avoiding future heart-break by not finishing it with her right now?   Are we too young to marry (we’re both in early early twenties)?

I feel silly writing to an “internet dating expert” (don’t take this personally!) but I don’t know who else to turn to.  

Love is complicated.

Thanks,

Chris

Love is complicated, Chris, and I’m sad to report that it just gets more complicated. The more you know, the more baggage, the more responsibilities, the more you realize you don’t know.

The more you know, the more baggage, the more responsibilities, the more you realize you don’t know.

So just be glad that you have many years to get burdened with the weight of life experience. In the meantime, to answer your questions in reverse order:

Yes, you’re silly for writing to an “internet dating expert”. As you know, everyone who dates online is a loser who couldn’t succeed with the opposite sex in real life. And when you account for the fact that I’m a 35-year-old single guy who has never had a relationship over a year – well, let’s just say you should be very embarrassed for even talking to me. I’m sure my clients, girlfriend, and mom all feel the same way.

Next: Yes, you are too young to marry. Sure, there are exceptions to every rule — my girlfriend just introduced me to her friend who got pregnant and married before she was 20 and they’re still together at 38. But this is beyond exceptional. Today’s generation — and even my generation — Gen X — can’t compare ourselves to our parents. The world has changed too much and everything seems to have been delayed ten years. I am of the full belief that 30 is the new 20, 40 the new 30, 50 the new 40, and so on. It takes longer to choose and establish a career; we have infinitely more dating choices; and gender roles and needs have morphed considerably. So while it would be nice and nostalgic to return to a time where 22 year olds had kids and grew up with them, like my parents did, it’s highly unusual. People simply change too much in their 20’s and 30’s….

If you don’t believe me, ask anyone who is five years older than you what they knew at age 27 vs. 22. Then try the same trick with 32 year olds. And 37 year olds. It is SHOCKING how little I knew five years ago when I first started this business. I had never been in love. I had never had my heart broken. I had never contemplated a future with anyone. But what I had done, Chris, is sleep with plenty of people. Which is a surprisingly important thing when you’re contemplating not sleeping with anyone else ever again. Your girlfriend has not had this experience.

For years, young kids got married so that they COULD sleep with each other. They’d get pregnant and since divorce was frowned upon, live a long, unhappy, responsible life with their large families.

Now that we’ve been able to separate sex and marriage, things are different. Women are more highly educated and are expected to develop their own careers. And while there’s still plenty of evidence of a sexual double standard, women are no longer under the illusion that their virginity should be saved for one man after holy matrimony. This is a double edged sword if you’re a guy. Because you should want someone experienced, you should want someone who knows what she likes and doesn’t, and you should want someone who doesn’t wonder what else is out there. Unfortunately, since you’re in such a serious relationship at such a young age, it would be impossible for your girlfriend to have that wisdom.

Because you should want someone experienced, you should want someone who knows what she likes and doesn’t, and you should want someone who doesn’t wonder what else is out there.

So you’ve got a real dilemma on your hands, my young friend. Because I would never tell you to dump a woman you loved to spare yourself the heartbreak. And yet I’d be irresponsible if I said that I thought you were going to have a happy ending.

If she’s determined to sleep with other men, you pretty much have two choices:

Break up with her and hope she comes back after some experimenting

Or allow her to fool around without telling you the details, and hope she hates it.

I think the first one will be hard to do, and the second one will be harder. But no matter what happens, remember, there are a lot of women out there — and you may just find that your girlfriend has done you a great favor by breaking up with you.