What It’s Like To Fall in Love With A Lesbian (as a Straight Man)

The heart wants what the heart wants. It is a timeless expression that rings as true today as it did when some British woman probably made it up after the man who was courting her vanished when she got pregnant (cool-yet-tragic backstory I made up there, huh?) but there is much truth to it. We, as human-beings, do not CHOOSE who we get romantic feelings for. We just kind of see or hear them and swoon. Problem is, just because we fall in love with them doesn’t mean they will always (or EVER) fall in love with us back.

As I learned the hard way, this rule is even more set in stone when you are a straight man who falls in love with a lesbian, which sadly, I have actually done more than once. But PLEASE allow me to stress the fact that we are not talking about “fair weather lesbians” here. AKA the sorority sisters who take enough Jager bombs they somehow think making out with one of their sorority sisters for male attention at a bar is legit. It isn’t. That is you assimilating a lifestyle for attention and for the wrong reasons. Fuck those fakes lipstick-lesbians, that shit is just sad because their Dad didn’t give them enough attention as a kid (potentially).

No, I literally mean women who are ONLY in love with other women. You know, lesbians? The REAL L word.

Quick spoiler, it doesn’t work out like that Kevin Smith movie Chasing Amy. When fat guys make movies about loving lesbians, it really doesn’t quite have the same impact loving someone who will NEVER love you back does. As a matter of fact, I think she switches teams at the end of that movie which just shows you HOW SEPARATED from reality the people in Hollywood truly are.

The real endings are far more depressing than the movies, as you all know all too well by now in life.

First of All, Why Lesbians?

Well, I told you in the opening paragraph that we don’t get to choose. Our hearts beat faster and get adrenaline when we see someone we are attracted to or interested in. It is literally chemical and biological. Thing is, when the heart feels that first burst, it’s not like you can grab it and say:

Hey, she’s literally not into you and will never be.

The heart just kinda goes forth into that cold night and wishes itself the best.

But there is another reason I tend to fall in love with lesbians.


I find lesbians incredibly easy to get along with. They don’t carry with them the stiffness and rigidity that can sometimes (necessarily) accompany the modern female. They also tend to like the exact same things I do. I do admittedly listen to alot of “lesbian rock” which I know sounds like a thing I made up but if you know who Ani DiFranco is, you know just what I am saying. And who DOESN’T love Ellen Page? And the cherry on the cake? We both love women. From the way they talk to the way they move to the finite complexity that goes along with them, Lesbian and I vibe on that alone.

Problem is, when a guy has a female friend he hits it off with and is attracted to, the brain doesn’t switch that off because she isn’t attracted to you. It just keeps pushing harder for the person, who in turn, is probably looking at YOU like a really cool friend who makes her comfortable BECAUSE she knows you know she is gay so you wouldn’t cross that line and disrespect her.

But it is super weird because the male brain just keeps yelling “kiss her, kiss her” and the most rational part of your brain is telling you to save yourself and HER the humiliation.

But yes, I tend to fall for Lesbians because they are kind of awesome people, and we do technically have “lock and key” genitals, even if they prefer opening things with scissors.

That was too easy, I’m sorry, this is how I cope with trauma. Laugh through the tears.

My First Lesbian Love (Sounds Like a Bad Fisher-Price Toy)

The first one was surreal because she was bisexual but with far more lesbian leanings, but at the time I had long hair and I swear to God, if you got drunk enough I mighta looked like a girl, especially if she looks while I am going down on her,. All she sees is long, Pantene hair, all dreamy and shit, which gives her the freedom to PRETEND I am a girl, therefore, actually reach an orgasm with a man.

Listen ladies, gay, straight or anything in between, I don’t care who you have to pretend I am or fantasize about as long as I “get you there.” Truth is, I am probably thinking about your sister during it. We all have our issues, but we learn to work with them.

What I also liked about dating her was that she would point out beautiful woman to me, which, at first, was REALLY cool, but later haunted me.


Because EVERY TIME we went out she spotted like three. As a man, I know what that means. That means she had “tiger vision” on and was always on the hunt. You don’t notice THAT many attractive people a day unless you are looking.

That’s when it hit me I can pretend the gay out of her in my own head, but that is who she is, because apparently everything with a vagina is attractive to her, which to me, was a scream for help and one I knew I couldn’t answer for her.

So I sat down with her and asked her if she wanted to date chicks for a bit (no threesome angle, just dug her and wanted her happy) and she fought it for like a month and then bounced and literally, never looked back. I was cool with it. If a woman is gonna leave me for something with a vagina, I can’t even be mad. I would do the same to her eventually. Humans are not the nicest things on Earth (dogs win that title).

My Second Lesbian Love (or) How I learned to Stop Worrying and Love the Lez

^Not a realistic portrayal by any means.

My second lesbian love was unique because she was a lesbian who claimed she “fell for me” which was unheard of (for a lesbian, jeez people, I am not a monster). We became good friends over a few years and she knew I was drawn to her and ignored it, then one day, SHE acted on it.

I could tell everything about me was pretty foreign to her (gender wise) but the sparks between us were palpable and I didn’t find myself threatened by her sexuality (though I should have, but let me explain that so it makes more sense).

The long term problem with someone with a certain sexual affinity abandoning that affinity is that it is ALWAYS only a vacation, only they don’t know that until they DO know it. We (straight men), on the other hand, think everything is fine. But now that I am older I am actually embarrassed to say I didn’t see it or the simple fact that I was willingly living in a blissful sense of denial.

That was not who she was.

She tried it, liked me, we had fun, I could get her off (I blame the long hair again, which has since been shorn to a mohawk) but at the end of the day, she felt like her love life was playing in a cover band when she knew she had the talent to play in her own, original band (that fit her better).

I hope that musical analogy made sense because I feel like it kicks ass, but this is also coming from a man who falls in love with women who love only women so I might not be the best baseline for judgement.

Again, though, at the end of the day I kinda felt like I was stifling her and that she would grow to resent me over time, so I sat down and had the convo and don’t you know, just like the other one, as soon as I opened the figurative door she split like a hungry dog and never came back.

And again, that was expected and that is okay.

We should be allowed to be who we truly are.

But, my dumbass goes and does it ONE MORE TIME because I like to be burnt over and over again just to remind myself of my own dependency on self-sabotage (maybe if I ONLY love lesbians I can keep from having a REAL relationship! Damn, someone call Freud, this is probably all about my f*cking Mom).

STRIKE THREE! My Third and Final Love From Lesbos

Yes, I know use of Lesbos there is wrong, but that is half the fun of being a writer. When you write these self-deprecating and overly honest pieces, one can use humor to negate the seriousness and heaviness of said topic, as well as the vulnerability you feel when sharing it with a world of faceless strangers..

The final lesbian (great name for a punk band, BTW, help yourselves) was the weirdest case of all because we had worked together, and she was full-bore with a woman when I met her. But it was there again. Those damn tiny fireworks. I used marijuana as a bridge to hang out. ‘Hey, you wanna smoke sometimes’ rarely fails in these modern times and is a lot better than the slimy pick up lines people used in the 90’s (“are your wings tired cuz you look like you just fell from heaven”, any woman who would put out for trash like that has to hate herself on a deeply unsettling level).

So we hung out and smoked.

And we hung out and smoked again.

And again.

The nights we hung out went from one hour to six.

And the convos went from the couch to the bed (granted, no increase in intimacy at that point, but still worth noting that we were physically warming up to each other) and one night I just kinda ate too many shrooms and she had too and I told her what was up.

I was like: I know you can never love me in the way I can love you, and I respect that, but I need you to know you are all I think about. Ever.

We sat there for a minute and sort of got lost in each other’s eyes (shrooms, remember) and I realized what was happening (I think we were gonna have sex, and she would have adored it DURING but would woken up hating her own guts and maybe mine and I couldn’t have that. That isn’t fair to her, so I walked her outside to walk her home (old-school gentleman style) and maybe it was the shrooms and our energy and the full moon that the shrooms made look like had a heartbeat, but at one point rationality broke and we kissed under that milky moon and it was amazing. Minutes felt like days, but in the best way possible.

Thing is, I felt that it would be both my first AND last kiss with her in one, so it had all the passion of a lifetime of love in one, three minute kiss under a pale bellied moon.

And afterwards, just like the others, she was all….

Alas, life goes on and I wish all of them true love, if such a thing actually exists.

My only suggestion to other men who seem to fall for lesbians.

They are awesome, your love is futile, accept it now and move on. Trying to change someone is not real love, anyway.

Love is the acceptance of someone, regardless of anything, and if we TRULY accepted them, we would accept that they are happier and truer to themselves when they get to love those who life intended them to love.

But hey, it never hurts to dream. I still have a thing for Joan Jett. The heart wants what the heart wants, afterall. We get very little say in the matter.

Featured image by Edwin Lee — Flickr.