Here's my situation: For the summer, I'm on the other side of the country for an internship, sharing an apartment with two other people who I've also been friends with for a while, one of whom I'm in the same room with. We work the same hours so we're home at the same time and generally speaking that's fine because he's a great guy and I enjoy spending time with him. I can't wear because there's literally no way I could hide it with the living arrangements we have. He knows I'm gay, the other person we're living with is transgender (she has her own room), and overall I very much doubt that he would have any sort of problem with it if I were to tell him. Hell, we've even joked about various fetishes and wearing diapers on a few occasions (I wouldn't be terribly surprised if he had some "tendencies" of his own). I've gotten to where I am seriously considering telling him, to the point where I actually have an unsent message sitting in a chat window to him saying I want to talk to him about something (he's away until tomorrow). I don't want any involvement from him, I have no fantasies of that (the thought of it actually makes me cringe). Having him know just means I would likely be able to wear at least at some points through the rest of the summer.
If I were home with my partner and I felt strongly about telling our other two housemates (not the same people I'm living with here) I likely just would, because I diaper up pretty regularly and so my feelings are more in balance. In all honesty I'd like to eventually just come out in some fashion to my circle of friends so I can wear (discreetly, I'm not in any way an exhibitionist) and not need to worry about them accidentally finding out, but that's probably a ways off for me. The feeling here is that I can have some opportunity to wear over the remainder of the summer, and that I can start on being less afraid of coming out and being found out.
The thing is, and the reason I'm looking for some thoughts, is that it's been a while since I've been able to wear, coming off of padding up pretty regularly so as far as diapers are concerned I'm fully aware that I'm not totally in balance emotionally. I need some sober input, even if it just bounces back some of my thoughts at me in a different light.