NiceGuyDTW Posted November 28, 2012 Posted November 28, 2012 Well I just finished up a screwed up "relationship", if you want to call it that. It was partially my fault for sticking out something that wasn't really there. But at the same time, she strung me along for a ride. ANYWAYS....I have a couple of prospects, and am looking to date someone a little younger than me (im 40, looking in the 33-38 age range). One prospect is...I think single...mom who I see once in a while at the school that my kids go to. She volunteers there during the day on occasion. I also know her from when her son was on the tee ball team I a coaching. Anyways, yesterday I was at the school for another matter. And I was walking through the hall, and saw her at a table helping a kid. As I walked by she looked at me and gave me a really nice smile. I think she recognized me, but the smile seemed more than that. It's going to be rare that I run into her. But if I do, I don't know where to start except to say "Hey aren't you so and so's mom...how are you doing?"...It's just that it would be kind of awkward to get some sort of connection with her in a school setting. Any ideas on how to proceed? I know this is a strange question, but just want some feedback.
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