Improv classes, dating apps and navigating kinks

Photo credit: Rachel Robinson
Rachel Robinson

Dear Dan: I’m a 30-year-old woman, and about a year ago I started taking improv classes to help combat my social anxiety. I met a lot of awesome people in my class, but I took a particular shine to this one guy. He was a gentle soul, very sweet and really funny. We quickly became friends. Eventually I developed feelings for him and asked him out. He appreciated the offer but told me that he was gay. I was shocked and disappointed, but I wanted to keep our friendship so I tried to get over my feelings. But not only haven’t these feelings gone away, I’m actually falling in love with him. He recently confessed to me that he’s still semi-closeted and dealing with a bad breakup so I really don’t want to add to his problems. This is such a mess. I found this wonderful guy who I care about and yet nothing will ever happen because I was born the wrong gender. What can I do?!?

—Introvert Makes Pass, Regrets Overture Very Seriously


Dear IMPROVS: Nothing.

You can’t make that gay guy fall in love with you, IMPROVS, anymore than I could make Hasan Minhaj fall in love with me. Getting over him is your only option, and that’s gonna take some time and most likely some space, too. (I’d recommend seeing less of your crush after this class ends.) But give yourself some credit for doing something proactive about your social anxiety, for taking a risk and for asking your classmate out. You didn’t take that improv class to find love, right? You took it to combat your social anxiety — and it sounds like you won a few battles, IMPROVS, if not the war. The takeaway here isn’t, “It didn’t work with him so why should I bother ever trying again with someone else?”, but, “I did it — I made a connection, I asked someone out — and I’m going do it again and hopefully it’ll work out next time.”

Dear Dan: I’m an early 30s hetero-flexible man in an open marriage with a bi woman, though both of us have been too chicken to actually go through on acting on the “open” part. Neither of us are hung up on jealousy, so that’s not a factor here. I recently confessed to my wife that I have had a long-standing desire to sleep with a trans woman. Yes, I know that it’s immature to not have disclosed all my kink cards prior to marriage, but I have my reasons, and thankfully, my wonderful wife let me off the hook and was very supportive. I expressed to her that I have considered seeing a professional trans escort rather than trying for a “hook up” situation. Her reaction was highly negative, as she has the impression that anyone in the sex trade industry is — by definition — a victim. Where do I go from here? I am uncomfortable with the idea of putting myself out there to meet a trans woman in my city (especially since I’m not looking for a relationship), but I don’t want to violate my wife’s trust and see an escort.

—Don’t Know What To Do


Dear DKWTD: Put yourself on a dating and/or hookup app, say that you’re partnered and only looking for something casual, and add that you welcome responses from trans women. Some trans women are rightly annoyed by all the cis men out there who only wanna hook up, DKWTD, and never date or be seen in public with them. But trans folks are just like other folks — some are taken, some are looking, some are taken and looking. If you get grief from a trans woman who’s annoyed that you aren’t open to dating women like her, DKWTD, let her vent — her frustrations are perfectly legitimate — while you wait for a response from a trans woman looking to buy what you’re selling.

P.S. The trans escorts I know — women who freely chose their jobs — will be surprised to learn that they’re victims, at least according to your highly opinionated and woefully misinformed wife. 

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