In Transit: the life and love flubs of an awkward single trans man

Jay is one of my favorite people, for lots of reasons: he is absolutely hilarious and naturally kind, he gives great hugs, spontaneously does polar bear plunges, can joke in puns for an absurdly long time, shares in my joy/misery of ridiculous single-life dating stories, and we both blog. Importantly, he takes pictures of himself while reading Roxane Gay, which I am also wont to do. It's a win-win friendship.In his own words: "Jay is thirty, single, awkward, and a transgender man. This is not where he saw himself at thirty, so he’s set off to get himself back on track, with hilarious results. You’ll cringe, you’ll laugh, you’ll cringe again, and you’ll relate to his accidental adventures. Jay’s life is In Transit."Jay and I decided a few formal interview questions, from one blogger to another, would  be our best way to introduce his blog to the FM community. Otherwise we'd ramble and engage in absurdity likely not appropriate for the internet community. So, without further ado, here's more from Jay and In Transit.FM: What brought you to write this book, and to release some of the chapters early?Jay: I’ve always enjoyed writing and on several occasions friends have said “you should write a book” after hearing some unfortunate dating tale of mine. I laughed off their idea at first. Then, as I thought about it I realized that my stories might resonate with people and it was an opportunity to achieve two goals; make people laugh and lift up one trans experience in a humanizing way that forces the audience to see me, a transperson as a person. I think humor is a powerful tool that can unite and bond people over complicated and nuanced topics. In my journey of writing this book, the feedback I got from authors I reached out to was to build an audience. They recommended a blog—which I was resistant to because a blog made it real and held me accountable to actually follow thru with this far-fetched idea!FM: One of the things I love about your blog, and corresponding chapter excerpt releases, is that it feels like it started in the middle of a conversation. The flow is the same way I always feeling when chatting with you, and I adore it. A lot of people tell me their plans about wanting to write more online but being worried to do so, worried to "put themselves out there"? How did you decide where to begin and how has the experience been for you so far?Jay: There’s a quote “If we wait until we are ready, we will never begin.” Or something—I’m paraphrasing. I held off for a long time. I wrote privately, journaling and occasionally sharing with close friends, because I, too, was afraid to put myself out there. I decided to just go for it, comforted by the fact that I could pull the plug at any time. This experience has been full of surprises and has been more thought-provoking and has caused more self-reflection than I ever imagined. When I posted the first few entries, I was nervous that no one would respond to it. I’ve been relieved to see people responding—and positively.FM: In "The Art of Breaking Up," you reference how in online dating, women don't owe men anything. As an online dater, I've struggled with wanting to be kind and feeling like there's a constant barrage of expectations that I don't want to respond to. How do you balance putting yourself out there and trying to show interest versus figuring out whether someone is not answering because they don't owe you anything?Jay: I think dating is challenging, period. It’s vulnerable for both parties and rejection hurts, even if you’re the most optimistic and confident person in the world. And online dating is even worse. I think people have this expectation that every message should be provided a response—and I disagree with that expectation. I’m no expert on dating and I’m pretty terrible at deciphering dating codes or signals. I basically need a neon sign with sound effects for me to realize someone is interested in me. I balance the energy online dating takes by limiting my time on dating sites. And I always acknowledge that I’m choosing to send a message to someone without knowing their interest/space/etc. and they are not choosing to hear from me. They get to choose how they respond—and a non-response is in fact a response.FM: Your post about deal-breakers is amazing. Are you working on a list of must-haves? What's your best strategy for deciding how short/long those lists should be?Jay: I think I’ve been trying to figure out what my must- haves are in a partner. As we grow I think that list changes—and I’ve also met certain people who changed what I thought for a must-have just because of who they were and the connection we had. So yes, I’m working on such a list, but it seems harder to write than the list of must-nots. My strategy for how long lists should be, is based on when it starts to feel like I’m getting too much in the weeds or if it takes more than 3-5 minutes to read.FM: What's the hardest part about being trans and dating? What's the best part?Jay: The added layer of vulnerability is the hardest part. And the fear that comes with that vulnerability. I think the best part is that I had a unique opportunity to really get to know myself and fall in love with myself during my transition which has given me a great perspective about what I’m looking for and who I am.FM: How is the current political climate affecting your dating experience? Jay: This is a very interesting question—and one I’ve been trying to figure out how to write a blog post for. There’s that old rule about not bringing up politics, religion or exes on a first date (which is probably rooted in trying to be polite and blah blah blah) I’ve never been one to follow that rule. I believe in the opposite. I want to hear about a dates politics and religious beliefs. Because if our opinions contrast greatly—then why waste each other’s time. In both my online profiles (Tinder and OkCupid) I state “If you voted for Trump or if you are racist or homophobic, don’t write me/swipe me, etc.” I think especially during these political times, knowing where and for what someone stands politically is important.As far as the political climate? As a transman existing in this world I have found my anxiety is higher than it was a year ago. Although I have a privilege of “passing” I also am a pretty public about being trans which makes me worry when people approach me and say “I saw you on the news.” I don’t know if the next sentence will be positive or negative. I worry about meeting someone I met online more than I used to. I worry about using the restroom (I write about this in Bathroom Debacle.) I worry about my friends who are trans. I worry. The political climate has changed my dating experience in that I am more cautious and anxious than I was previously. People are a lot more vocal about their transphobia now. Which allows me to identify them easier, but doesn’t make me feel safer.FM: When I'm writing stories about being a midwife that overlap with patient care, one of my struggles is how to write from my experience and not talk too much about people who haven't necessarily consented to having their story told. It's a hard balance. In healthcare land, it's a bit different than dating land, but it seems like already in your writing you're finding a good balance there. How are you negotiating that space of writing about your life and others' lives in such a public way?Jay: That’s a challenging space to negotiate. I try to use my own narrative—so that it is clear that the story is mine and through my eyes. I’ve also reached out to some exes to ask permission to share our story—even going as far as asking some of them to write their own pieces about me (I thought it was fair)FM: What's next for your blog and book? How can people find out more?Jay: Next for the book is finding a literary agent for it (anyone? Bueller? Ha.) As for the blog, I continue to post every Wednesday and it can be found atwww.intransitmemoir.com or on Facebook at https://www.facebook.com/intransitmemoir/.