When to tell, someone you're interested in, you're f2m? From age 12 to about 20, I'm ashamed to say I had quite a few short-term relationships, that I never revealed who I was. They'd either find out through the grapevine, or I'd disappear before they had the chance. I had a 2 year relationship from 21-23 where the girl had known me through family for years beforehand, so it was easy to jump into that. That ended and I met another super cool chick, we "talked" for 2 months before being official, and I made the huge mistake of not telling her, and when I did, I'm grateful she understood and we stayed together, but it ended for different reasons months later.
I've recently been talking to a girl, who after a month, I got the balls to tell, and she's been cool with it. But it's so damn hard for me to just TELL them. How do you go about doing this, how long do you wait, how do you even bring it up? 95% of the girls I talk to are "straight". I don't know if this matters, or not.