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Dilemma on how to proceed with older woman
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So I'm 25, and she's 45. She was my literature teacher in high school and during the last half year we talked fairly over facebook about books and life in general (corona times). One of the first things she said back in March that she and her husband are divorcing. Last month we finally could meet up despite her having a ton of work to do, plus she has 2 children, and she just moved after the divorce. It was a really pleasant evening with a couple of glasses of wine and nice talking (sometimes flirty), she asked if I had a gf, I said no. After that I walked her home, kisses on cheek and said goodbye. Next day she told me she had a really good day because of me, so I asked if we could meet up again if she has the time, to which she replied "but what good does it do for you my dear? you don't have to waste your time and attention on me". I said it's okay, I don't feel like I'm wasting anything on her and I enjoyed the evening really much and that I insist. She said ok, we'll find the time. This was 3 weeks ago and since then we just talked about general life stuff on facebook but next week we'll both be free, and I aim to ask her out to meet up. Any general advice on how I should proceed? I really liked the time with her and I can imagine being with her but she's in a tough spot now with all the stuff that's going on and maybe she doesn't need more complications now. Also I'm really bad at giving/recongizing flirty signs. And, as you can probably tell, I'm a huge over-thinker when it comes to women. Thanks in advance for any advice.

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4 years ago