Dear 100 Hour Board,
If there's an apartment of three girls, and I want to ask out two of them, what is the best thing to do? Ask them both out at some point? Or just pick which one I should ask out and not ever ask out the other one?
The best thing to do would probably be to not ask out either of them. I mean, whichever one you picked would probably ghost you eventually anyway.
You can likely get away with a first date with each of them if you put some time between it (probably a month or two). I know people have differing opinions on this, but I've done it a few times and it's been fine.
Once upon a time it was Sadie Hawkins week in my ward where girls were supposed to ask the guys out on dates. Just for the heck of it, I made plans to go on a date every day (this actually turned into 10 dates... I think the Saturday of that week I went on three dates). Anyways, I asked out two guys who I didn't know were roommates over the phone about five minutes apart from each other while they were both apparently sitting in the living room. They weren't offended though. I have a vague recollection that one of them told me later that he had "mad respect".
Anyways, I wouldn't worry about it too much. A first date is a pretty casual thing. I don't know I'd call them five minutes apart, though.
I've asked two girls from the same apartment out within a week or two of each other, and it didn't affect my friendship with either of them. Well, my friendship with the second one was affected for a while, but that was because she would rather be avoidant than say no, and had nothing to do with having asked her roommate out before. I went on one date with the first and two dates with the second, and I'm still friends with both of them, but I have no idea what would happen if you tried to go on multiple dates with both of them at the same time.