Should I ask an old friend if he wants to try dating again?

I have an old male friend he's 16 years older. We went on a few dates over a year ago. We talk for a while then we go for months without talking. Just recently I texted him saying I would like to talk and I just ended my engagement due to it not working out. My friend said he thought of me more as a friend a year ago. He is on the same dating site I am on. He said a few days ago he's given up on finding anybody. Should I flat out ask him since neither of us have found anybody yet would he want to try dating again?

When I told him about two months I was engaged he never responded. When I told him I ended my engagement he surprised me by not only responding but by also asking why. I didn't think he would respond let alone ask why.

We get along great. We have a lot in common. Even when we have bad misunderstandings like we did last year we are still friends. So should I flat out ask him if he would want to give dating another try?

Please only polite answers.


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What Guys Said 1

  • 1. I don't believe in settling or giving up for lack of others options that don't come quick enough. If you settle, then you'll regret and wreck that deal when finally the ideal arrives, leaving others broken in your path of haste.
    2. If the goal is only friends, then we'll see what happens, then your best course is to either ask him to join you in a mutual activity/drink/food/place for conversation OR be needy enough to NEED a "partner"/escort to a venue not entirely objectionable to him.


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