When I was at Va Tech, two older NCOs (late 30s, early 40s) were watching the pretty young ladies walk around campus.
One of the NCOs mentioned how great it would be to have a relationship with one of these young women.
The other (the wiser of the two) said, "What would you talk about the morning after?"
I went away thinking (besides the creeper factor), "You know, that is a good question." When I was in my late 30s/early 40s, I had nothing in common with a 20-something. Music, literature, life experiences? Nothing.
I have no idea what Belichick talks about with this woman.