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Thread: Dating an older man - advice needed

  1. #31
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    Default Re: Dating an older man - advice needed

    Quote Originally Posted by toughcookiegirl View Post
    Update: We had gone out on one more date and neither of us were feeling it too much so we agreed to be just friends. He also indicated that our personalities were quite different (which I'd agree, but I feel like I don't really know him well enough). Generally, to me, when I tell someone we should be just friends, I don't plan to see them again. But, sometime around the holidays he texted me and we texted back and forth. And then I texted him, and he asked if I wanted to get dinner next week. I wasn't expecting that, but I said "sure" figuring we'd be just friends. But, then I canceled dinner saying it was bad weather and he asked to reschedule to the following week. So this week, we finally had dinner. He offered to pay, but I insisted on splitting (since we were just friends). We talked well past dinner was over. He didn't try anything physical (he never has). Thing is that I am somewhat attracted to him (and that's more than what I can say for most of my recent dates - ugh), or at least enjoy his company (and I think he does too or he won't have asked me to have dinner, especially after I tried to cancel). Anyway, I know it's unlikely, but any chance it could still go somewhere?
    Sounds to me like you are dealing with a guy with some serious baggage. Divorced? Commitment issues? I would see other people. Keep yourself busy. Be sexy but not overtly. Be you. But don't TRY to attract him. You wouldnt want to do that to yourself. Fastest way to know is always to get the person a little tipsy. Trick is not to drink too much yourself... otherwise you give it away. Also if for some reason they get tipsy and show less interest you will be in the right frame to just shrug it off.

    If you are really ballsy (figuratively of course) you may want to introduce him to another male friend. Maybe have some one else walk you to the bar or restuarant you are meeting him at. Say NOTHING as to who it is. What the nature of the relationship is. But make him wonder.

  2. #32
    toughcookiegirl is offline Aspiring PUA
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    Default Re: Dating an older man - advice needed

    I have no idea about his past - we just never got into talking about it.

    He also did something else kind of weird. We had first met at this social happy hour that recurs every month. We were both signed up for the one in January, and then he texted me: "Not that it has any bearing on you, but I won't be able to make it to the event on Tuesday night because I am flying out the next morning to go to Chicago. Just as well that we caught up the other night!"

    IDK what "not that it has any bearing on you" means. And I have no idea why he's even telling me / checking in? I mean, it's cute and all that he feels like he needs to do it or wants to do it, but based on my dating experience, most guys wouldn't have done that. So I was pretty confused, but texted him "Too bad. Have a safe flight; can catch up later" And then he texted "Yes, looking forward to it." (and then said something that implied he thought I was really smart). And then he texted again the next day to let me know he saw the happy hour was cancelled because of the weather.

    So...maybe he just wants to be friends, and unless he drops down to the ground on one knee and suggests otherwise, I am not assuming any different. And that's fine with me because I barely know him and am not 100% sure of how much I like him or how compatible we are, and plan to continue seeing other guys. It's just odd that he is being so communicative, reaching out, checking in, when he doesn't need to. I mean, some of my ex-bfs didn't do that and technically, I am not even dating this guy!


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