Dear Andre,

I’m a 50-year-old gay man falling for a transgender man for the first time. The feelings seem to be reciprocated, but lately I’ve found myself hesitating to take things further than flirtation. Not because I have any personal qualms about being with someone trans, mind you, but honestly, I don’t have any trans friends and am just generally worried that I’m going to say something “stupid,” or be a terrible lover, or something else that will screw this up before it even starts. Help!

Marc F.

Dear Marc,

Breathe. You’re doing a good job.

Transgender folks are among the most vulnerable populations in our society. While physical assault and fatal violence disproportionately impact transgender women of color, all transgender individuals are subject to an onslaught of daily micro and macroaggressions. These can be as “mild” as being misgendered, dead-named, or facing other kinds of psychological and emotional bullying, and as “severe” as homelessness, employment discrimination, or a complete lack of access to healthcare services. Or, you know, having your federal government leak a memo seeking to define “transgender” out of existence. No biggie.

Unfortunately, trans people can’t even count on the rest of the LGBTQ community to have their backs. Many times, cisgender partners of trans individuals place their own gender identity and presentation expectations on their partners, and/or internalize a partner’s transition to mean something about their own identity. Other times cis folks fail to recognize the privileges they inherently carry that their transgender partners do not and can belittle their partners very valid concerns, particularly around safety and “passing privilege.” Additionally, trans people are often heavily fetishized in our culture, and even the queerest of cis people can sexually objectify their trans partners. The act of “chasing” is, indeed, rooted in a cultural assumption that the only reason someone would want to be with a trans person is because of a sexual fetish.

If interested in a trans person, you should first do your homework on the systemic oppression that trans folks face (beyond writing to me, that is!). Develop an informed understanding of how intersecting trauma can permeate the various levels of a trans person’s life, including romantic and sexual relationships, and get comfortable acknowledging your own privilege. Consume media that is written or produced by trans people, Listen and believe trans voices, and get involved in local initiatives that benefit the trans community. Don’t be a lazy ally!

With all this being said, trans people are human beings before they are anything else. Before you approach your love interest as transgender, try approaching him as a person. Ask him what kind of cuisine he favors, and then invite him to dinner with you! It’s really that easy. If the date goes well, follow up with another one soon thereafter. Don’t put the cart before the horse and allow your anxieties about potential future sexual fumbles or long-term relationship inadequacies distract you from enjoying yourself and determining whether you and this man are even romantically compatible in the first place!

If after a few dates’ things seem to be going well, go ahead and open up to him about your concerns. Reinforce how fond you are of him, let him know that you’ve never dated someone trans before, reassure him that it is who he is as a person – not his “trans-ness” – that you are attracted to, and recognize that you’re still a work in progress who is asking for his patience. It’s not only “okay” to admit when we lack knowledge about a certain identity, demographic, or experience; it’s endearing. It shows that you are comfortable accessing your vulnerability and confident confessing ignorance around a sensitive topic.

Finally, you need to accept that your love interest may opt out of dating you based on your inexperience, and that’s okay. Sometimes marginalized people don’t have the emotional spoons to be someone’s “first” no matter how wonderful a person you may be.

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Author Profile

Andre Shakti
Andre Shakti
Andre Shakti is a queer journalist, educator, performer, activist, and professional slut living in the DMV. She is devoted to normalizing alternative desires, de-stigmatizing sex workers and their clients, andnot taking herself too seriously. Andre wrestles mediocre white men into submission and writes about the resistance for Rewire, Thrillist, MEL, Vice, Cosmopolitan, Autostraddle, and more. She frequently lectures,coaches and advises on the intersecting issues of sexual health, politics and pleasure, race, trauma, gender diversity, sex worker rights, non-monogamy, and queerness. When not working, Andre can typically be found marathoning "Law & Order: SVU" under a chaotic pile of partners and pitbulls, and yes, she knows how problematic that show is. In addition to her work with Baltimore OUTloud, Andre is the reigning polyamory pundit at her biweekly non-monogamy advice column "I Am Poly(amorous) & So Can You!", which you can visit - and submit questions to! - via She encourages you to connect with her on Facebook via "Andre Shakti" and follow her NSFW exploits on Twitter via @andreshakti!