So here's the situation I'm in. I have this friend from High School. We didn't really start to hang out until maybe halfway through senior year. She had a boyfriend at the time but eventually she didn't and I was into her, but never made a move because 1) betaproblems and 2) we were gonna be leaving for college eventually anyway. We stayed in touch a bit and occasionally hung out during breaks.
Last weekend I had my five-year high school reunion. It was the first time in about a year that I had seen her. We talked and joked and it was good. I'm going to be seeing her on Monday to play some tennis, and when I do, I'm planning to ask her to a Twins game.
tbh this is the point where I should stop thinking, but I'm not going to. I can't help but try to over analyze this before it even happens, and that's a major flaw.
I've never asked her out on a date, which is my intent here. Whether or not she'll pick up on that, I don't know, but I'm assuming she will. But since we've been friends for a while, I don't know for sure. I'll try to figure that out based on her reaction. I know it's possible that she'll ask about my intent and I'll tell her.
But it's if she doesn't that is where I am stuck. Do I bring it up right there? Or do I wait until the day of and bring it up after (if I felt good about how it went)?
Obviously situations will differ based on the people and the exact nature of the relationship between them, and since you guys don't know these things, you may be unable to help. I don't really know what I'm looking for from you, maybe just a general idea of what you think I should probably do, or maybe just words of encouragement. idk, but just talking about it makes me feel better about it.