I’ll couch this post in several warnings/qualifiers:
In this post, I’m going to discuss my experiences and observations regarding dating men and women. I’m going to limit it to cisgender (a person whose self-identity conforms with the gender that corresponds to their biological sex) partners. Experiences with my transgender partner are unique and outside the general scope of this post. (I’ve spoken with my ex and he’s given me permission to write about our relationship more in depth at some point. Stay tuned for that!)

Furthermore, since I only have experience with dating one woman (and marrying her and subsequently divorcing) my experience may be a bit limited in that. Though I have the experiences of friends to corroborate my stories and feelings.  

So really what I’m saying is I’m just gonna tell you about how I feel. Which is what I always do here so why would now be any different?

Get ready for a ping-pong match of compare and contrast stream-of-consciousness wordvomit on this general subject. I make no guarantees where this will end up!

So…dudes. I love them. I suppose you could have called me “boy crazy” for many years. There is something endearing about their “otherness,” their often bumbling cluelessness.  

This charicature was commissioned by my dad when I was 8

Despite my rampant feminism, I still appreciate the feeling of being protected, and, every once in a while, pampered. I enjoy taking that feminine role in the partnership (most of the time.) 

In contrast, being with a woman is so comfortable because of our sameness. I understand more deeply how her brain and emotions work, and the stereotypical “I’m fine doesn’t always mean I’m fine” mind games that they somehow insist on playing. Though I often acknowledged in my relationship that I was the “dumb boy,” and still didn’t understand why she was upset and wasn’t all better after taking a nap. I mean, I felt fine.  

Being with a partner who was a butch woman, I still felt those gender roles…in some ways almost stronger than when I dated men. She was raised to be a “southern gentleman”–in fact, she told me that in her first OkCupid message to me. She made sure she always walked on the outside of the sidewalk to shield me from splashing puddles and traffic. She was offended if I was able to open pickle jars when she couldn’t. She was threatened by my stereotypically “masculine” qualities because that was her role in our relationship.  
For the most part, I’ve always dated fairly romantic guys. I’ve received my share of love poems in various levels of skill and expression. Often times, I felt like the clueless one, even in these heteronormative relationships. Sure, I can have a bit of a sensitive streak, but I’ve always been a realist.  

My wife was definitely a romantic. But the problem was that it meant that I needed to learn how to reciprocate with the romantic gestures. I’ve always thought being given flowers was a stupid waste (they were going to die anyway, and were a huge burden on the environment,) but I learned that she enjoyed getting them. So this is what guys felt like. Having to remember to do things for chicks that they don’t care at all about. I began to sympathize for all those generations of boyfriends and husbands.  

When I actually bought her flowers she cried and then Instagrammed it

So then I wondered what it would be like if I had dated a more feminine woman. I can appreciate a pretty femme, but they’re not “my type.” They were my ex’s type, and I was the most androgynous girl she had ever dated by far.  

There was one time in Union Station in Chicago that I bought some breakfast at a little shop, and the black cashier complimented my shaved head and referred to me as a “stud,” which is generally a term used to describe butch black women. I was kind of flattered and amused, and I told my wife. She was actually a little bit upset about the fact that I could be viewed in such a masculine way, and I think that it threatened her own butch-ness. And called attention to the fact that her wife was not the femme with the flowing hair and lipstick that she had imagined she would end up with.  

But what if I was with another androgynous woman (definitely my type) or a femme (yeah, probably not?) I wonder how those “traditional gender roles” would shake out. In my same-sex marriage, I felt them just as strongly, if not stronger, than when I was dating men. Is that just the way we are programmed to pair up? Is that why straight people ask “who is the man and who is the woman?” to gay couples?   

We took turns, quite honestly. My wife had to learn that it was okay to cry in front of me. She had been with many partners before who hated it when she was “soft.”  

I assembled the IKEA furniture and she color-matched her underwear to her shirt and ties. 

While she always dressed in a more masculine way, I shifted from my hoodies and chucks to dresses as the seasons changed. But she always cared more about her appearance than me, obsessed about her hair. I could get ready in 10 minutes flat. It was her I always waited on. 

Though at our wedding, I wore a dress.  She wore a suit.  We both wore Chucks.  


Women are wild cards. Unpredictable. Inscrutable at times. I wonder if I feel this way because I think my brain is wired a bit more “masculine,” logical and methodical. But then I catch myself acting in similar ways. Ah, femininity, you fickle creature.
And let me tell you the single worst thing about “lesbian” relationships: two periods. (Once again, cisgender relationships. Not all women have periods.) And we never synced up (our cycles were both stubborn) so there were two weeks a month in which we needed emergency chocolate and copious apologies for having All The Feels. But we deeply understood this time, and could be there for each other in a way that male partners never could. 

But dudes can be pissy assholes any time of the month. I had a friend who once told me “I’m pretty sure that guys have a PMS cycle too, but it’s every 24 hours.” I don’t know if it’s quite that extreme, but mood swings are not exclusive to women.  
I’ve dated some pretty progressive men who accepted and appreciated my empowerment and dominance. The Guy I Thought I Was Going To Marry even agreed he would take my last name, because my sister and I were the last with our surname.  

With The Guy I Thought I Was Going To Marry

One of the most awesome things about being married to a woman was No Unplanned Pregnancies Ever. It was a convenient excuse that shut up the “when are you going to have kids?” question. Two ladies having a kid was expensive any way you looked at it, so that was a great way to keep nosy people from inquiring.  

Quite honestly, the possibility of babies is the single worst thing about dating guys again. But with my shiny new copper IUD, I won’t have to worry about that for another 10 years. 

The last time I held a baby was in 2012 and this feeling of terror regarding them has only intesified since then

The first time I kissed a woman, I was shocked at the difference. It’s so much…softer. That’s really the best way to describe it. More intuitive. That sameness again, self mirroring partner.  

But there’s something great about the rawness of kissing a man. Something primitive and slightly dangerous. There’s a different kind of trust that I employ, and it’s exciting.  
I never felt as safe walking with my wife as I did with a boyfriend. And it’s not just because we were visibly gay. Even without that aspect, I have always felt more protected by men. A part of me hates that I feel that way, the “weaker sex,” but a part of me loves the feeling of being treasured and shielded.
And then there’s the issue of LadyGaydar. Namely, I have none. Yes, I may have been married to a woman, but I still couldn’t pick out queer ladies and tell if they’re flirting with me or just being nice. Like, it’s really difficult. Like…I can’t do it. Even if a woman is totally androgynous looking, clothing wise and hair wise, I don’t want to assume anything. When I first shaved my head I was straight-identified. I’m pretty sure that, short of a woman coming up and kissing me or straight-up telling me they’re queer, I wouldn’t know.  

I’m pretty sure this is the gayest I’ve ever looked. I think it’s the plaid.

Dudes are much more transparent that way. I admire their forwardness and no bullshit approach. I love knowing exactly where I stand and not cloaking meaning in riddles and codes. I’m not lying when I say that, on more than one occasion, I have asked a guy who I’ve been kind of flirting with “So, do you wanna make out?” (The answer has never been no. #baller) 

Cut through the ridiculous dance of questioning intentions. That’s what I’m about. 
But I still have this inherent mistrust of guys. (I wrote about it at length here.) That same raw danger that I find so intoxicatingly sexy is also what I fear most.  

I always wonder what their end-goal is, and if they’re being honest with me.  

At the same time, I used to be quite the “maneater.” I was a pro at divorcing myself emotionally from a situation, sometimes causally juggling three guys at the same time. Usually. 
I hold potential ladies to a higher standard than I do men. I don’t know why. Maybe it’s because I have had less experience with them, or maybe it’s because I have had a history of so many casual relationships with men they have become less precious to me. At any rate, because queer women are already less plentiful than men and I’m way pickier about them, the odds are likely that I will be dating a lot more men. 

But who knows. As I told a friend earlier this week, “my sexuality is fluid and it ebbs and flows like the tide,” (she wants that on a t-shirt.) I’m interested in people. Men, women, and everyone in between or outside those silly boxes. I’m open for it all.  

Even if men are dangerous assholes and women are crazy bitches.  

They’re also pretty cool. 

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One thought on “On Comparing and Contrasting Dating Men and Women, or Men are Assholes and Women Are Crazy

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