Sex & the Single Woman: What If Your First Boyfriend Is The One?

Elderly Couple

What would you do if your first boyfriend was The One?

My roommate and I were recently driving home from Chicago when this question drifted into our conversation. We both agreed that it is important to date numerous people before ultimately settling down, but what happens if your first one is the One you are meant to be with for the rest of your life?

I think that over the course of dating, aside from the different experiences you get, you can kind of compare guys. Yes, there was the first boyfriend, the one you wish you never dated, the one who you really liked but you just didn’t see it going anywhere, and the One who made all of the other heartbreaks worth it. If you only date one guy, how will you be able to realize how fantastic the relationship with your perfect guy truly is?

On the flip side, if you meet someone with whom you want to grow old, why waste time looking around for what you have already found? Is it a mistake to only date one man before you marry him?

Like most women, I have dated guys that in retrospect I realize I never could have married. Even if it seemed like there was potential at the time, I now know that I am better off. I think I grew from these experiences (yes, even the bad ones), so even though I didn’t end up marrying any of these guys, I definitely don’t regret them. But I’m still left to wonder, what if things had turned out differently?

What do you think—could you marry your first boyfriend if you thought he was The One?

–Maggie