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To pursue or not?


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I am recently divorced, and have started considering dating. I became interested in my ex sister in law, we have been friends for a long time, and she has been a great support during my divorce. We had been texting each other off and on for several months. Some of her text seemed like she was flirting with me. I am totally aloof to such comments and didn't quite know what to say. She had said things like when I asked her how she was doing she replied that she was feeling lonely, but was better now, being completely clueless I didn't pick up on the fact that she was better now because I texted her. DUUHHH! Another example, I texted her to see how things were going she replied I need more hope than that from you, then lightened it up by with JK. I asked my therapist what was going on, she said shes flirting with you. DERP! So I got the courage to ask her out to dinner, and she brought along my niece, whom I adore. When we were seated at the table, my niece sat next to me, and my ex sister in law sat across from me, she made a comment to her daughter that, "oh you get to sit next to Mister handsome" I was flattered by such a comment. Well the dinner went great and we had a great conversation. She even texted me after dinner that she had a nice time, and hoped she didn't talk my head off. I told her I loved every minute of it. She had also extended the invitation to come over weekends to hang out with her and my niece.

 

Now this is where it goes downhill.

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Please tell me this is your ex wife's sister. If so, you should absolutely, totally, with out a doubt go for it and post back here often and frequently. If it's one of your siblings' ex's, then my answer is just 'totally, with out a doubt go for it and post back here often and frequently'.

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So I started texting her the next day with comments like hope you had a nice day, and if you ever want to talk, or do lunch just give me a call. I told my therapist the next week about the text I had been sending her, she pointed out that my text are very generic and could be perceived as just wanting to be friends, which is not what I wanted. I really wanted her to know how I felt about her, but wanted to take things slow, but didn't really do that on the dinner date. Well I wanted to ask her out again, and kept texting her If I could call, (why text just call duhhh).

Let me explain that I work shift work and, and I happened to be on nights this week, and I have a rule that I don't make major decisions or have emotional interactions on a high level until I've gotten some rest, just the way it is. So what did I do, called her when I was feeling like crap, and she was felling like crap, she had a bad day as well. The conversation went something like this " Hey would you like to go out again, I really enjoyed last week, she replied she couldn't that she had family coming in for the weekend,(crickets chirping) I went blank and said UHHH OK well have a good week talk to you later" What a dork. I felt horrible, I didn't engage her at all, how was her day, how was she feeling, family coming in what they were planning NOTHING. I felt so bad so I called her that evening, she didn't answer so I left a light upbeat message apologizing for earlier, and that I should have waited to call when I was alert. AARRRGGGHHHH. I really like this girl and we've been such good friends for so long I felt horrible I treated her that way.

So I don't know what to do now. I haven't talked or texted her in about 5 days, since she has company and all. Just thought I would let things be for awhile. I am confused, was she really flirting or am I just misreading signals? Should I try again but keep it really light?

I like a comment I read earlier to just "let things happen organically". And that was my earlier intention but I let my brain get in the way of good judgement. Should I tell her how I feel? Or just hang out for awhile and see what happens, if she will, not so sure now?

 

Well any thoughts or comment would be greatly appreciated.

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She's my brothers ex, they've been divorced quite awhile, she is closer to the family, than he is, we don't see him hardly ever.

WIll1988, What so you mean by the possible sh** storm, sorry I'm a little slow. But I can laugh about my aloofness, and learn from these mistakes!

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Will you are right about the sh** storm from that aspect. I gave it a lot of thought before pursuing her. But she is worth the storm! All storms fade, if things work out, great, if not lesson learned.

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