On asking her out
My PSA for the day -
Guys, when making a date, you need to include a specific date, place, and time.
"Maybe we could go out some time," isn't making a date. It's you, passing the monkey of making a date, off to her. Plus, she's not going to realize you're wanting her to ask you out. She's going to simply answer your question.
And don't say, "pick a place and a time, and I'll let you know if I'm free." Her answer will likely be "nowhere," and "never," given you don't think she's worth the bother of having something in mind.
What's prompting this post? One of my neighbors is mad at me. According to him, he's asked me out for at least a year, but I've never accepted. His asking me out? "Maybe we could get a drink sometime," to which I'd reply, "okay."