“How do I ask her out?”

I went to high school 2 years ago with a girl whom I never talked to until now, as I am shy about meeting people. She recently moved back in town after a pretty bad breakup, though I don’t know the details. I’ve gotten out of a relationship with someone who cheated on me twice in the last 9 months, as well.

I think she’s really beautiful and deserves someone who is loyal and treats her with love and respect, but I don’t know if I should say anything to her about how I feel, as I’ve sorta only texted her for 2 weeks. I asked her out for coffee, but I haven’t gotten a reply. I’m an awkward texter, so I’d rather talk in person where my charm is.

“How do I ask her out?”

There is a girl at school that I have been interested in for a long time. We have never really talked much but she seems like a lot of fun, and she isn’t bad to look at either. My problem is that I seem to be caught in an awkward middle-zone where I’m having trouble figuring out how to proceed. I’ll explain.

I don’t know her well enough to ask her out based on a pre-built relationship the two of us have. We’ve talked a few times, but never much. At the same time, we’ve been in each others’ vicinity for almost three years now without anything ever happening, so I can’t really take the “introduction and ask out” approach. Continue reading