'Should I ask my office crush out on a date?'
I have had a crush on someone from my department at the office for a few months now. He seems like a nice guy, and we get along well, so I have been tempted to ask him out for coffee or a drink. I don't know if this is a good idea though, because our office has a problem with people dating. I also don't know if he likes me enough to come out with me. I don't know much about his personal life either, so I don't even know if he is single. Should I go ahead and ask him out?
There are a number of things to think about first. Your office has a problem with co-workers dating, which means you as well as this boy will need to be brave enough to test that. You don't know him well, so the possibility of him being single is as high as the possibility of him dating someone. You like him, but aren't aware of whether he reciprocates your feelings. I suggest you try and chat with him more often, get to know him a little better and try gauging how he feels about a potential date before you make a move. If he gets to know you better, you will know more about his life and be in a better position to figure out what his reaction may be to you asking him out.
Two weeks ago, someone I have been friends with for a long time asked me out to dinner. It seemed like a romantic proposal because he said it would just be the two of us. I like him, but I don't know if I'm attracted to him because I have never given this possibility a thought. Should I go out?
Of course. This is a friend. Go out and see what dinner with him is like, and whether you like the idea of him being more than a friend. Maybe it's just dinner. You won't know until you show up.