I (23M) have had a crush on this one girl (24F) for a long time and we recently reconnected after a few years back in June and I realized I still have feelings for them. At the time they were seeing someone, and as disappointed me I was still happy for them and glad we could still be friends, but a few months later they broke up and ever since then I’ve been thinking about asking her out. She’s gonna be in town for Christmas and that’s when I was thinking about asking her.
I don’t know if she’s currently dating someone because we rarely talk about that sort of thing and I don’t know what kind of guys she’s into, but I still want to ask her the question because I don’t know when the next time I’ll see her will be. She lives far away and is always busy with work or something, but we still find the time to talk at least once a week despite all of that. We’ve managed to work through long distance before so I think we could manage (but obviously I’m not certain). We’ve been close for a long time so we wouldn’t need to worry about ice breaker questions or introducing each other to our families.
I’m just kinda nervous about asking her the question. I don’t really know how to bring it up in a way that won’t weird her out because like I said we never talk about our romantic relationships. How do I ask her if she’s single and then ask her out without making things awkward or uncomfortable for us? I really want to ask her, but I also don’t want to lose my best friend because I tried to take our relationship farther than she was comfortable with. I really love this woman, I have ever since I first met her, and I think I’m finally at a place where I feel like we could be a good couple even though we live so far away from each other. I know she’s really looking for a long term relationship with someone and has had a lot of difficultly finding that, and maybe this is just me being naive, but I think that due to our history and how long we’ve known each other as friends that things will go well and I can provide her with the relationship that she’s been looking for. I can’t confirm that for sure, but I like to stay positive.