Whom should I tell first?

I am trying to figure out whom I should tell first. I don’t think there is a right answer, but I think each person has upsides and down sides. Eventually I will tell them all, but the first is special. I’ve chosen people that I know will be open to it, and I suspect that this probably will not surprise any of them.

Cast of characters:

My twin brother: we have a pretty closes relationship, but we have never really included one another in our dating lives or personal problems. We are only recently becoming more open about talking about this stuff.

Friend #1: My bromance. If he were gay (which is he most assuredly not) I would totally date him, since I am madly in love with him. We are really close friends, and I know he would be totally chill with it. Downside: he is not the most emotionally expressive person and he has told me that he doesn’t really experience a wide range of emotion. I am also afraid that he might find it weird all the times we were affectionate or joked about spooning (or sometimes a bit more risqué than that).

Friend #2: one of my oldest friends. He came out at the end of high school and had a pretty rough time finding himself, so he definitely knows what I am going through. We are close, but we rarely talk about our personal lives. He is kind of awkward, and I am worried that he might hold the time that he was out and I was not against me.

Friend #3: She is going to be my roommate next year and is one of my closest friends from college. We get on great and she is an incredibly affectionate and supportive person. We just have never really talked about personal stuff before. Also, when I first met her, I asked her out (she declined).