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Ask her on a date and see where things go?

Dear Prudence,

I recently reconnected with a former female co-worker who was/is a very good friend. We had lunch with a mutual friend, and her behavior caught me off guard. As the three of us were laughing about our time together in the same office many years ago, she leaned into me and kissed me on the cheek. Not once but twice! The third member of our party excused herself to go to the restroom. After she disappeared around the corner, my friend leaned into me again and whispered, “I just realized that I’ve never kissed you before.” I looked at her and said, “Let’s talk tonight after we have both eaten dinner.” She agreed and we talked for almost three hours about anything and everything like we used to. At the end of our conversation, she apologized for her behavior that afternoon and I told her not to worry about it. I’ve often wondered if we should have tried dating on a serious basis.

We have always supported each other in a times of need. In the past, she cried on my shoulder after her first husband committed suicide and once again when she found her second husband in bed with another woman. She also cried on my shoulder daily after her mother passed away. She was also more supportive than my ex-wife after I had dual strokes in 2016 and went above and beyond after both of my parents passed away.

My question is, now that we are both in our mid-60’s, do I pursue a serious relationship, given our past history?

—Do I Or Don’t I?

Re: Ask her on a date and see where things go?

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