I’m interested in this woman I’ve known for over a decade. We met through working at a low end diner and became close enough that people would call us my work wife/husband. When I first met her I had the huge crush on her but she was in a relationship, and when they broke up I was in a relationship, so things never really aligned.

We would try to hang out outside of work but it was never successful most time. On her side I feel like her anxiety would make her cancel, and for me I would over think the date and feel like I’m not in the position to take her on a great date she’d deserve and not confirm plans. There was only one time where we went on a double date and it was amazing and we both had a great time. And when we moved on to different jobs, I would make attempts to see her on her lunch break, up until we moved to two separate states and locations

We’ve definitely talked about our feeling before and she’s said in the past that she had a crush on me too, but at this point the relationship was long distance and I wasn’t in a place to be able to visit her. We wouldn’t always stay in consistent contact with each other but when we do we would have conversations that would last weeks or months over text, having thoughtful conversations and flirting, but it never ended up dating and I regret a lot that I never took that chance.

We recently started to talk and catch up again and the vibe is still the same, but at the moment I’m living overseas. I would love to be in a relationship with her, I love everything about her, but I don’t know how she would respond. It would be a long distance relationship for the moment and I don’t know that maybe I’m just being delusional about it being a real possibility.

So I’m asking about how I should go about it? I’m sorry if this is confusing or not enough information for I’m trying to process like ten years of history and there’s quite a few more factors involved that I haven’t mentioned yet.

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