Been seeing this girl for years on/off since school. We hook up whenever she is in my city. I started to want to take things further and be exclusive, so I brought it up to her and she agreed. This was about two weeks ago.

She was always really ‘laddish’, but not in a brash, try-hard way. She was more laid-back than other women I’ve been with. She never wore dresses or make-up, always in jeans and with short hair. Kind of dominant in bed, but that’s what I like, and she REALLY likes anal. At work she’d wear a tie sometimes. I just thought he had a kooky style.

She told me last week that she thinks she is transgender, ie she thinks she’s really a gay man. (S)he said (s)he wanted to be honest with me as we’re dating now, not just fuck buddies. (S)he’s talking things through with a therapist.

The thing is, I’m not sure I mind too much. (S)he is funny, laid-back, and we have a great time together, shared hobbies etc, so I’m willing to give it a shot. The thing is, if (s)he goes through with changing, I’ll be in (what looks like) a gay relationship.

That’s not how I identify. I’ve always seen myself as a fully masculine, red-blooded guy, and I’m feeling really strange about exploring this potential new identity. Anyone have any experience of this? Could it work out? Am I gay? Should I just move on and find someone who fits the usual profile, or have a stab at being with my best friend?