Dear Steve and Shirley, I’m a 39 year old divorced man and I’m the head coach of a high school girls basketball team. My female best friend works with me as my assistant coach. We met 7 years ago and bonded over our love of basketball. She’s a single mom and a straight up tomboy. She wears sweatsuits and sneakers all the time, no makeup and her long hair is always up in a ponytail. I joke with her about being more feminine but she said she’s sworn off dating for now, because her child’s father broke her heart……………..
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