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.
Dear Captain and Crew, I am transgender, FtM, or at least that's what I came out as several years ago. Since then, I have become increasingly isolated due to work, debt, and extremely debilitating mental illness. I'm doing my best to sort those things out (moving to a place where friends are, looking for a … Continue reading #493: I’m tired of being trans.
Dear Captain Awkward, First of all I'd like to say that I'm not even sure if this is a problem or if I'm just making problems up because clearly SOMETHING in my life has to be going wrong (I frequently second guess myself, but that's a separate issue) but here goes anyway. I was born … Continue reading #291: How do I know if I’m trans*?
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?