After Transitioning, Valentine's Day Has Become More Confusing Than Ever

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"OK, man, look — it’s right there at the top. The bit with all the folds." My co-worker Frankie* and I are huddled over my phone in the men’s bathroom in our office. I’ve pulled up a still from a porn video and I’ve zoomed in as far as I can — I’m trying to show him where the clitoris is. After transitioning, Valentine's Day has become more confusing than ever for me. This isn’t the strangest thing a cis guy friend has asked me around this holiday — but it feels like it’s one of the most urgent.

Usually the questions I get from my friends around Valentine’s Day are pretty simple. People ask, "What does she want?" — as a gift, during sex, for dinner. It always makes me laugh that these boyfriends think I know their girlfriends (many of whom I’ve never met) so well just because we have a chromosome in common. Every so often though, a guy like Frankie will take me out to lunch and blurt out over barbecue, "So, wait, where exactly is the…" and he’ll whisper the word "clitoris" into his Diet Coke like his mother is one table over.

"You see? It’s there. It’s not inside," I say, trying to clarify it for him.

"Yeah. Yeah! Right. Outside. Sure," says Frankie, nodding anxiously.

He’s a good guy, barely 22, and I want him to feel comfortable asking other men difficult questions like this. So much of being good at anything is about confidence, so I’m trying to give him a little boost.

"Look, man, she’s a person just like you. So, just think about if you’d like something before you try to do it to her — and ask. Always ask," I advise.

Frankie nods again and thanks me, and then scurries back to the office. I meet his girlfriend a week or so later. She gets lunch with us and when he goes to the bathroom she leans over and says, "Thank you. Thank you so much," and squeezes the top of my knee.

I’ve been a man for seven years this year, and Valentine's Day always creeps up on me. Somehow, when I was a lesbian and in a relationship with another woman, none of the corporate gender crap around the holiday seemed to apply to us. My girlfriend and I made a big deal about it some years, and some years we didn’t, and no one seemed to care.

When I became a man, a lot of people wondered if my girlfriend would break up with me, but labels were never important to her, and we stuck it out. It took her some time to get used to me having facial hair, but nothing substantive between us shifted. On the outside, though, we went from being a visibly queer couple to what looked like a "straight" one, and that came with a whole host of challenges I wasn’t ready for, including being a boyfriend on Valentine's Day.

I’m standing in our bedroom, holding out a gift I bought for my girlfriend for Valentine's Day, hoping that I didn’t screw the whole day up. "I… I don’t know what happened, hon," I explain. "There was champagne. And then the sales guy started showing me things and…look, if you hate it, I can take it back." I’m holding out a small Tiffany bag and my girlfriend is staring at me.

She unwraps the gift, a heart necklace — a Tiffany classic, the sales guy told me — and smiles wistfully. "Oh, hon," she says. "You got bamboozled by a jewelry salesman!" She kisses my cheek and puts the necklace on.

I know she’s humoring me, and later we’ll joke about all of this, but I still feel good watching her clasp the sterling silver heart around her neck. I wonder later maybe if this is some weird possessive impulse I’m developing, like toxic heterosexuality creeping in at the seams of our relationship, but when we talk about it later she laughs at me kindly. "It’s just funny because a family member got me the same necklace for my Bat Mitzvah!" she says, and I can’t help but look a little downcast. "No, no! Honey, you did the thing! You got the jewelry for the girlfriend! You tried really hard and that’s what really counts!" I agree that in future, I’ll consult one of my sisters or my gay best friend before I buy my girlfriend jewelry that she hasn’t seen or shown me herself.

It can be tricky, this Valentine's Day stuff. So much advertising is aimed at men: Buy her this perfume! These flowers! This necklace! If you don’t, how will she know you love her? If you don’t, how will she know that you can provide for her? If you don’t, how will she know you are even a man? Buy her these things or you are nothing!

Of course, there’s a lot of advertising out there aimed at women, too — all of it much more sinister. Lose weight for Valentine's Day! Look younger! Don’t be alone! Men are told to buy things and women are told again and again, to be good things to buy. To me, it all looks like a trap for everyone involved.

Still, I like the idea that one day a year, we tell each other we love each other. Being in a long-term relationship is hard even when it’s with your best friend, so it’s nice to have a built-in excuse to spend time with each other if you need one. If it were up to me, Valentine’s Day would be an excuse to get all of your friends together and tell them you love them, to call your parents and siblings and tell them you love them, too — I’m even all for getting your dog a little extra treat, too. A little more love in this polarizing world goes a long way.

Last year, my buddy Andy asked me what to do for Valentine’s Day. "I haven’t really been a good boyfriend in the past you know, and I really want to blow her away," he told me. "Like, I think she’s it and I want her to feel like she took a chance and it paid off." Disarmed by his earnestness, I didn’t brush him off with a joke. Without sounding too much like a relationship counselor I told him that at the root of any good relationship is communication, and that asking doesn’t take the romance out of anything. I wanted to tell him that women aren’t mysterious creatures; they aren’t sphinxes spitting riddles that one must solve to gain their affection.

"Just ask her," I suggested. "Just be up front. You can riff on a theme you know? Or make notes on what she likes, even if it’s something small. She’ll see that you notice her and want to care for her, and I think that always goes a long way."

Andy nodded, his brow furrowed. He thanked me, but I could tell he was still stuck, and I felt bad for not giving him something more concrete.

"Pizza," I said, sighing. "Pizza and oral sex. She shouldn’t touch your d*ck. If at any point she’s touching your d*ck, you’ve done it wrong."

The next day, Andy shook my hand, pulling me in to say in a low voice, "Best Valentine's Day ever."

*Name has been changed.