Friend zoned: but with future trip planned

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    Dear Question Asker,

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    I’m 64 yr old widower, friends with 56 F widow. Started as friends, I made it clear after a couple of dinners that I felt we could escalate. She made it clear that she wasn’t totally feeling it, the exact spark she had with her ex wasn’t there, but she was willing to give it time and see if her feelings developed. We shared some passionate kissing. Also explicit texts. Close, but mixed signals.

    During the friendship phase we planned a trip. Just as friends. Trip approaches, I tell her I’m feeling some anxiety traveling in some undefined limbo. She clarified she never felt any spark and really hoped I could be her bff, she really likes me as a friend.

    She also casually dates other guys, and I was casually dating as well, though my dates haven’t gone anywhere.

    I’m trying to figure out how to be the better man, enjoy this long weekend that I’m paying for, as a friend, to thread the needle between being an angry dick and submissive doormat.


    #114170 Reply


    I can totally answer my own question:
    1) I am a big boy and can be a friend for a few days, and then refocus on what I need.
    2) I can set some boundaries on things that just rub salt in the wound like having to listen to anything about her other dates and nonstop what a saint her ex was
    3) I can plan self care activies that give me joy regardless of where she’s at

    4) DON’T EVER DO THIS AGAIN, plan travel with someone thinking we’ll start as friends but she’ll see what a great catch I am and come around. Setup for disaster.

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