Are You Not Entertained?

If you're not having fun on dates, what's the point?

I tend to reject the notion that dating is difficult, and I say that as a 33-year-old tomboyish transsexual woman, hardly a mainstream option for much of the population. It’s okay, it makes me feel less bad about having such high standards myself.

For me, date quality tends to fall pretty consistently into three categories. If the chemistry is there, the date is a blast right from the start, and you worry about shit like life compatibility further down the road, or maybe in hour 19 of the date if it’s with a lesbian. These are the dates I live for. One of the greatest feelings in my post-transition life is when a date is firing on all cylinders and you get the sometimes much-needed reminder of how fun it is to throw yourself out there in this chaotic world.  

The second is the “nice time” affair, where you don’t necessarily feel the sparks, but you enjoyed the activity and the company. Nothing wrong with a nice time. For people like me who enjoy the act of dating, nice times are a decent outcome.

The third super sinister category is rather excruciating, the awkward trainwreck that begs the question: why is this happening? Romance of one of life’s great extracurricular activities. It’s completely optional, no matter what the Broadway musical Company might tell you (maybe don’t see that show live if you’re a terminally single 33 year old woman).

You may have been on one of these before. You had a pleasant conversation, either on the dating apps, or the analog world, before agreeing to go out. The sparks may or may not have been completely there, but you’re still excited for the chance that you might meet someone special, because you’re a confident soul and the world looks kindly on those with confidence and an open heart.

You get to the date, and shit just feels off. I tend to avoid scheduling dates on Mondays for this reason. Vibes are an imperfect way to gauge anything, but an empty restaurant full of people stressed that the work week has only just begun is not super conducive to a pleasant date atmosphere. Nobody feels sexy on a Monday, which is why most Broadway shows take that day off.

Plenty of us can have bad dates on any day of the week, not just Monday. The ones that drive me nuts are when the other person is completely disengaged, straight from the get go. Efforts to start conversation go nowhere, and the whole thing feels like a job interview rather  than something that is ostensibly supposed to be fun.

Sometimes, you’re in the middle of a terrible date with cringe conversation, and all you can think about is asking them if they realized that they did not in fact have to be there.

One of the most persistent compliments I receive is for my smile. As someone who lived with awful gender dysphoria for a quarter of a century, smiling did not come easy, or natural for me. I had to learn how to smile, not just smile like I meant it.

A smile can go a long way toward setting the stage for a good date. I can’t control if my date wants our dinner to be a long trans-101 session, with every ridiculous question under the sun (no, the penis does not grow back, yes I’ve been asked that question on a date). I can’t control if they’re awkward as shit.

What I can control is my smile. A lot of people get nervous on dates. I do not. I look at dates in basically the same way I approach social media. Life’s short, make a splash, be yourself. Be weird. Take up space. My profiles are all engineered to reflect my personality, so there shouldn’t be any surprises when people go out with the eccentric transsexual.

I am fully aware that a large chunk of the population has written me off as a viable romantic option before we’ve even met. That doesn’t stop plenty of them from going out with me for a night. I could be angry at the way the world teaches too many people to auto-dismiss trans folks as serious dating options, but I don’t want to be mad. I want to have fun.

A couple of years ago, I did a Pride Month interview with Rotten Tomatoes that ended up being mostly a barrage of ITM greatest hits from my podcast, as I warned the interviewer that I wasn’t much of a film critic anymore. The pandemic hit the day after I finished all my trans surgeries. I came alive as the world came crashing down around me. If I have to build sand castles in the rubble of the apocalypse to have fun, I’ll make some damn good ones.

In that interview, I turned to the subject that serves as the title of this post. Being trans means that I have to engage the world with a fairly shitty hand of cards. There’s only so much I can do to deconstruct people’s preconceived notions of my community. I don’t want to spend my life pushing that boulder up a hill.

Life is filled with optional activities. When you’re doing anything that exists outside of the realm of your basic survival, it is always important to ask yourself this one question:

Are you not entertained?

I don’t go into dates assuming I’m going to meet the one. I don’t even go into them thinking I’m going to have a second date.

I do go in thinking I’m going to have a good time. I commit to that notion, because without it, what’s the fucking point?

One time in college, I took some mushrooms with some buddies. Naturally, as college sophomores are prone to do, there were some philosophical discussions. I was later mocked for my somewhat simplistic view of life as “if it’s fun, do it,” but I think there’s probably worse lodestars to follow.

Last year, I was in a non-monogamous relationship for a few months. My girlfriend at the time asked me if navigating those was challenging. I told her that it was more tedious than anything, with many people in open relationships having a tendency to spend entire dates talking more about the theory of non-monogamy than enjoying the date itself. My words “Shut up and play the damn game,” resonated with her, and served as a big theme of our time together. I did a podcast episode on this subject the day after our first date, which she confessed to listening to multiple times (generally a bad idea to re-listen to any ITM pods that aren’t Thomas the Tank Engine themed).

I find myself constantly asking myself the question, Are you not entertained, not because I like Gladiator (not my favorite Ridley Scott or Russell Crowe film), but because it’s the most important question you can ask with regard to your extra-curriculars.

Good things come to people who engage the world with intention. You aren’t always rewarded when your throw yourself out there with an open heart. But even after a shit date, you can still head home with the knowledge that you showed up, and played the damn game.

Note: We’ll have two bonus posts this week, a film review that fitting for our dating conversation, and another addressing the current situation with Facebook. Much love, fam.