I'm out, fully out

As Process pointed out, once you miss the chance to out yourself early in a relationship (platonic or romantic) with someone, it becomes more and more difficult to come out again. So with that in mind, I recently outed myself to M. We were talking about experiences having friends that we've had sexual chemistry with. I may lie by ommision, I won't lie by commision. So in my response, I acknowledged that the person I was talking about was a woman.

It was nice and we talked a bit about it. Later in the week we were out walking and I ended up mentioning the ADD (which I normally don't share with people who are or are potential work peers) and he asked me if I take meds for it, which I acknowledged I do. It's hard for me to be out to someone w/o ADD as an adult with it. Most of my friends have it; we do attract each other. But for those who don't, there is a serious lack of understanding. When I acknowledge that I take medication for it, I still feel some transient shame.

We keep spending large chunks of time together. I'm a little nervous because it is beginning to get the flavor of a potential relationship and I'm finding my feelings changing from brotherly/friendship to friendship/potential partner.

This isn't good for a couple different reasons. Reason #1: he's acknowledged having a pattern of sleeping with his female friends and having that mess up their friendship and of having a lot of unprotected sex in the past. To remedy this, he's cut back on his drinking a lot, started therapy (for reasons broader than this), and explicitly told me about this because he doesn't want to mess up our friendship.

Reason #2: He's two months post a breakup from a year long relationship. That one stands by itself.

Reason #3: He says that he has a habit of supporting a close friend or significant other emotionally for a long time and not getting his needs met and then he disappears suddenly and hurts them.

So he is not a good dating partner right now. But when there is that connection, I am so hesitant to let it go. There are so few guys who I really like and who are emotionally open. I am still averse to dating women right now (baggage) and now that I am becoming interested in him, I hate to lose it. All my friends are in relationships right now and it is really hard to be the only one that is not. Plus, we'd have really cute red headed children.