Dater XY: My Best Friend Is A Woman

My best friend is a woman. My best friend in college was a woman. In fact, a majority of my closest friends since college have been women. And this presents a problem in my dating life.

There isn’t one single reason why I have more female friends than male ones and if you looked at my weekly activities, it would seem strange that I don’t have more male friends. Every weekend I enjoy traditionally masculine, rip-my-chest-hair-out activities, like hockey and football. Yet it’s my female friends who I tend to call when I want to go out.

For starters, I do have a somewhat functional brain that is capable of functioning independently of my penis (albeit the little guy does occasionally develop a Napoleon complex). This has led to several of my close female friends starting out as love interests. Others I met while on my college’s ski team. Additionally, there is the fact that most of the closest male friends I had in college were the earliest to get married and have kids.

I hate the way too many men talk about women, from questions like whether I “fucked her” after the first date or whether or not I’ve seen the Jennifer Lawrence nude photos. Women (and gay men) also seem to be more fun. Not that men can’t be fun, but if you really just want to engage in shenanigans, women seem to be the most up for it without fear of how cool they will look. All of these things led me to forming close relationships with various women I’ve encountered over the years.

I fully understand why a close female friend might be an issue for some of my love interests. If you’re looking for a partner, you’re looking for a best friend — albeit a friend you find sexually appealing and want to fuck the shit out of, but a best friend nonetheless.

So, as the question always goes, “If your best friend is a woman than why aren’t you dating her?”

“I’m not attracted to Sassy Pants,” I’d reply.

“Sassy Pants is incredibly attractive and you’re best friends! How could you not want to be with her?” They ask.

The answer is simple, but yet never fails to confuse anyone. See, I’m capable of thinking with more than just my penis. I’m capable of having deep and meaningful relationships with women I find attractive. The simple fact that Sassy Pants is good-looking doesn’t mean I have to try to get in her pants or feel romantic feelings for her. It’s easy to be friends with someone of the opposite sex for me and I think it is for most individuals if they are able to get beyond the limiting societal expectations of male/female relationships.

Recently, I had a first date with a woman, Red, who didn’t seem to believe this. We met for pizza and things seemed to be going well; we generally liked the same things, had a lot of common interests and things looked to be heading for second date territory. Until that is, halfway through the date Red asked me if I had a best friend. I had no idea how she felt about opposite-sex friendships at this point, but I answered honestly. I told her about Sassy Pants and the usual questions commenced.

Red couldn’t wrap her head around me being friends with a woman, asking the usual questions of why I wasn’t dating Sassy Pants instead. It didn’t take long for both of us to recognize that there wasn’t going to be a second date because of my best friend. I can’t say that I was disappointed with the outcome, though: whoever I date is going will need to accept that my best friend is a woman and we’re not going to let dating complications affect our friendship. What is disappointing, however, is the collective amount of times I’ve had otherwise potential relationships cut short, or not even start, because the other party wasn’t comfortable with my closest friend. Just within the past week, there was the date with Red as well as two women I messaged online that all stopped when they learned of Sassy Pants.

If someone I’m seeing isn’t comfortable with my friendship with Sassy Pants, so be it. Nor do I expect anyone I’m seeing to be 100 percent comfortable with it from the get go. I understand the apprehension and I’m willing to work with it, like including the woman I’m dating in activities and conversations with Sassy Pants so she can see we are just good friends. I want to be as open and honest about the relationship as possible — both because it’s the right thing to do and to prove I have nothing to hide.

[Image of male and female friends via Shutterstock]