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Thread: Work Dilemma

  1. #1

    Work Dilemma

    I own my own business who has contracts with other businesses. I was invited to a soft reopening by a customer of mine to give feedback on there procedures before opening back up to the general public. I was talking to the woman who invited me for about 5 mins.

    About a minute after she leaves another woman walks up to me and says "I bet you don't remember me" I look at her and I am thinking about it when she says "We sat next to each other in Spanish and English Class you also played baseball with my brother". Then it clicked we talked for about a minute and she had to go because she was working. I didn't see her the rest of the time I was there. I wanted to see if she wanted to catch up. I don't know if she is even single. I did have feelings for her back in High School but that was 12 plus years ago. How should I approach her. I do stop by her work like once a month to drop things off. I don't necessarily want to ask her out right away but more of a catch up first and see what happens since we haven't seen or spoke in a long time.

  2. #2
    Platinum Member Wiseman2's Avatar
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    Next time you run into her, ask to go for coffee to 'catch up'. Then you can assess whether she is single, interested, etc. Alternatively if you have a business connection of some sort, connect to her on social media or LinkedIn.
    Originally Posted by javajones
    I wanted to see if she wanted to catch up. I don't know if she is even single. I did have feelings for her back in High School but that was 12 plus years ago. I do stop by her work like once a month to drop things off.

  3. #3
    Platinum Member Rose Mosse's Avatar
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    I'd opt for the more direct approach. Catch up over coffee or a lunch and ask her if she is free.

    That leaves the ball in her court to either decline if it feels inappropriate to her or to accept if she's interested. Keep it simple.

  4. #4
    Platinum Member Cherylyn's Avatar
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    ^^^^^^^^^^^^^^^^^I agree with what Rose said.

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  6. #5
    Thank you all for the advice. A funny thing happened. My work friend texted me and said that she the girl i knew from high school asked her about my situation like single or not and wanted my number. We have been texting and are going hiking this weekend.

  7. #6
    Platinum Member Wiseman2's Avatar
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    Excellent, have fun. Bring snacks.
    Originally Posted by javajones
    the girl i knew from high school asked her about my situation like single or not and wanted my number. We have been texting and are going hiking this weekend.

  8. #7
    Platinum Member Rose Mosse's Avatar
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    Bring water too. That's wonderful.

    Have fun!


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