Dear Dr. Romance:
Should I say something? I'm reaching out to you for advice, I came across your blog recently and wanted to see what you had to offer. I'm kind of in a weird situation, I'm interested in this girl that I work with, we have great chemistry and make each other laugh non-stop, we also hangout outside of work and enjoy each others company. I wish I could tell her how I feel about her and how I want to see her happy all the time. She just ended a relationship about 4 months ago, from what I've heard it was a pretty serious relationship. I just wish she could know how I feel, sometimes it's so hard to hold back from saying something. What should I do? Hold off from saying anything and just continue hiding how i really feel?
If she ended a long relationship four months ago, she may not be ready to date anyone else yet, even if you are close to each other. If she's hanging out with you outside work, then it seems to me she'd know the possibility that you'd like to date her does exist. It sounds as if you have a light, easy, fun friendship. It's OK to ask her if she thinks she'd ever be interested in more than a friendship, but be prepared for a negative answer. If she says she isn't, or she doesn't know yet, you'll have to go back to just being her friend. If she says she might like that, but it's too soon, then keep things light, but consider asking her out for a real date, where you make all the arrangements and take her somewhere. Then follow my "Guidelines for Successful Dating" . Try to keep your expectations low, so you don't frighten her off by overwhelming her. I don't see any reason why you can't say you'd like to see her happy all the time, or that you really enjoy her company. Just don't get pushy, and you should know before too long if this is ever going to develop into a more definite relationship. If it doesn't, read "The Fine Art of Squirrel Hunting" to get into the dating world. The Unofficial Guide to Dating Again will tell you all you need to know to make dating fun, safe, and successful.