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I knew she was expecting me to propose while we were there — it was a layup.

On the night of our big anniversary date we went to the nicest restaurant on the island in some new clothes we bought just for the occasion, but there was no ring to be found.

So imagine that you just met your now-ex — at a party, work, school, gym, with friends, in the hot tub — whatever would be plausible now at your current ages and location. We were comparing notes about our recent dating lives. And our frustration at finding a sweetheart who had the means, time and desire to travel, and who had mutual attraction.

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My friend was in the restroom waiting with a change of clothes and the most beautiful diamond ring you could imagine.One assumes that love is reciprocal, but of course, it’s not always.[click to continue…] Tagged as: 40 dating, boomer dating, Dating after 40, dating after 50, Dating Goddess, dating over 40, dating over 40 advice, dating over 50, dating over forty, mature dating, midlife dating, online dating book for women over 40, over 40 dating, senior dating One of the most common items I see listed under men’s “What I’m looking for” area in online profiles is “drama free.” It makes me scratch my head wondering why it’s so common.I quickly put on my suit coat, grabbed the ring and took a deep breath. Her mother and brother had flown in from New York for the special occasion and, just as planned, they came out from where they were hiding to surprise her.After a long embrace with her mother, she turned around to find me on one knee.

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