Should I reconnect with an old flame?

I am a middle-aged attractive woman and I have a friend I have known for years. I have known him since I was about 19 or 20 years old and we dated briefly when I was that age. We both ended up marrying others and having children. We are both now divorced and we are both now single and in our 50's. We lost touch for a while but now we got in touch again on Facebook.     


He asked me to go to dinner and I feel very reluctant because so many years have passed that I would feel awkward now. Also, my family and his family all know each other so it would feel awkward for me if something happened between us. I told him I would think about it but he became insulted and said I have known him long and asked why I would hesitate. I am puzzled as to why he would ask after such a long time. Is it rude of me to say that it would feel awkward for me?

3 Answers

  • Helen
    Lv 7
    1 month ago
    Favourite answer

    The fact is, if you haven't stayed in touch all these years then regardless of your previous friendship, you are no longer friends. His interest is purely romantic.

    It's understandable he was offended by your snub, but lying to him would be worse. It doesn't seem as though you're in the right frame of mind to rekindle anything.

  • Anonymous
    1 month ago

    My late husband and I had the exact same situation. We married at 52 and had 10 wonderful years together.  Go for it!

  • 1 month ago

    I wouldn't take it well either if I was him because I would see it as a rejection of friendship, not a rejection of romance.  You seem to be forgetting your past relationship was more about being friends and old friends tend to like to reconnect.  You, instead, are getting ahead of yourself battling the idea of a romantic relationship that doesn't exist yet. 

    Should you explore the possibility of making your friend more than a friend?  I don't know.  It doesn't sound like you are ready to start dating people because in asking this question you have already effectively talked yourself out of going out to dinner with him.  When you ease up on your arguments, then you might be ready.  I just hope you don't pass on too many prospects, you might miss someone good.

Still have questions? Get answers by asking now.