#978: “If you were a ten-year-old boy who just told your mom you’re gay, what would you want her to say?”

Hey Cap, Hopefully this is any easy one for you (and maybe your community?) If you were a ten year old boy who just came out to your mom, what would you want her to do or say? What could the mom do to support him? He came to me crying and handed me a … Continue reading #978: “If you were a ten-year-old boy who just told your mom you’re gay, what would you want her to say?”

#844: “Bracing myself for when conservative relatives find out about my gender transition.”

Dear Captain Awkward, I'm 37 and DMAB but identify as agender tending towards feminine. I have long been socially "out" to my friends, and I medically transitioned years ago although I've maintained a male presentation. But that's finally changing - as of now I am finally transitioning publicly and in my family and professional life. … Continue reading #844: “Bracing myself for when conservative relatives find out about my gender transition.”

#812: “Coming out as transgender at the holidays.”

Ahoy, Captain, So, the holidays are coming, and there are some issues which I am pretty well obligated to deal with, but have not yet (being a weenie, largely), here's a list of facts: - I am transgender - I have started hormone therapy (testosterone), my voice has dropped noticeably, I should probably shave, and … Continue reading #812: “Coming out as transgender at the holidays.”

#548: I met a cool person to flirt with and I’m scared of what to do next.

Dear Captain Awkward, So I met a girl last night, one I've run into occasionally when the orbits of our respective circles come into gravitational alignment. We spent the time chatting together and exchanged numbers afterwards. I have zero experience with romantic relationships, but what little knowledge I've accumulated from rom-coms and trashy novels leads … Continue reading #548: I met a cool person to flirt with and I’m scared of what to do next.

#528 Reaching out (and coming out) to exes after a long time away.

Ahoy Cap’n, This isn’t a particularly dramatic question, but I’m stumped. I’m a dude who would like to say he’s in his mid-twenties, but probably can’t anymore. For a long time, I would have said I was straight. I was attracted to women, dated them and had relationships with them.  Then, a couple of years … Continue reading #528 Reaching out (and coming out) to exes after a long time away.

Guest Post! “If I come out to my family, will they stop making offensive jokes already?”

Question:  How is coming out to your family like admitting that you've never seen The Evil Dead in a room full of nerds/filmmakers/filmmaking nerds? Answer:  Those two things are in no way similar. Which is why I called in reinforcements for this question. Please welcome Julie and Jessica, the filmmaking duo known as King is … Continue reading Guest Post! “If I come out to my family, will they stop making offensive jokes already?”

Question #38: Guest Post! How do I tell my conservative dad that my fiance is about to become my fiancee?

Dear Captain Awkward: I'm not in an awkward situation yet, but I probably will be soon, and I want to be prepared for the awkward. My current fiance is probably going to be starting to transition into being my fiancee pretty soon. This is not a problem for me. However, I think it will be … Continue reading Question #38: Guest Post! How do I tell my conservative dad that my fiance is about to become my fiancee?