Should My Sexually Inexperienced Boyfriend Sow More Wild Oats Before We Marry?

My boyfriend and I are in our late twenties, live together, and have a very healthy, equal relationship. We speak comfortably and openly about our problems and insecurities, but there is one we just can’t seem to solve: I have had a significantly larger number of sexual partners than he has. I spent my early and mid- twenties however I wanted: I bought a home by myself, I went to concerts alone, I backpacked through the mountains with pals on weekends. And I had casual sexual relationships with men and women whose company I enjoyed. To be clear, I was always responsible, mature, and sober. I did not lower my standards to get laid, or market myself as a “bimbo” for attention. I just really liked people, good conversation, and sex. I had great experiences that helped me determine what compromises I could make and what behavior I would not stand for, and I eventually realized that men and women can have equal partnerships and respect each other.

My boyfriend is the opposite. He is a serial monogamist who can count the number of women he’s kissed on one hand. We were friends for years before getting together, and even when I tried to wingman him at bars, he was never interested in casual hook-ups.

Now, he might sometimes tease me that I’ve been with more girls than he has, but we both agree that numbers don’t matter and that the past is the past. The problem is that both of us have these little bits of doubt. He worries that I’m too hypersexual to be satisfied with just him, when really, I never would have committed if I felt he stifled me in any way. If anything, I am glad that I have dated and experienced such a variety of partners. I am 100% confident that I want to be with him, unlike some of my friends, both male and female, who married before they discovered exactly what they wanted out of life or a partner and now have Grass is Greener Syndrome.

So while my boyfriend worries that I want some exotic fling, for the first time in my life, I am happily hunkered down at home with someone I have real feelings for. On a similar note, however, I do worry that he hasn’t experienced enough variety to be so certain about me. Don’t most men want to sleep around? We have been talking about marriage and it will break my heart if five or ten years down the road he decides he needs more than just me. I have even suggested that he go on a trip with friends and have a free pass to at least MEET other women. His past relationships were with sexually conservative and religious girls and I am by far the kinkiest, so I worry he doesn’t know what else is out there. Even when we were just friends he would tell me he was too shy to hit on strangers. Is he settling for me because I was bold enough to make the first move?

I have heard many times from men that they could never marry a girl who had a higher number of sexual partners. Do I need to encourage him to take some time to be a little promiscuous before he marries me?

Vittoria

Dear Vittoria,

His insecurity is that you will not be satisfied with just him.

Your insecurity is that you will not be satisfied with just him.

Try taking “yes” for an answer and enjoy your life with this shy, devoted guy.

If you assure him that you’re satisfied with just him, both of your insecurities go away.

Your boyfriend doesn’t want more sexual experience. He’s satisfied with what he has right now, a kinky, hypersexual woman who wants to marry him. Who could blame the guy?

Try taking “yes” for an answer and enjoy your life with this shy, devoted guy.

Love,

Evan

P.S. If you need more than that, check out this email from a man whose girlfriend wants to get more sexual experience before she settles down. I don’t predict a happy ending for them.