If you had a really good connection with your roommate/best friend, would you try to start dating her? (not just hooking up)
Or would you wait a couple of months until you don't live together anymore.
Why would or wouldn't you, and how would you bring it up if you did consider it?
Most Helpful Guy
In short and from my own experience, no.
I've had female roommates twice, and both times I had or developed feelings for one of them. The first was a long time crush that I had always liked, but decided to wait until after we moved out to ask her out. She ended up saying no, and while we've been able to remain friends, it saved a lot of awkwardness going through it after we were no longer roommates.
The second was in a long-distance relationship that everyone knew was falling apart. We had gotten flirty with each other, which culminated in us sleeping together cuddling on our couch one night. I knew I probably could have, but didn't want to get in the middle of an existing relationship, so I didn't pursue anything further.
So yeah, from my experience, waiting until you're not roommates has been preferable from my point of view.0