I would disagree, in some ways.
If he wanted the chance to meet new young ladies, then these community events are great opportunities.
High school football games are full of young adults, and college gets, not just HS kids. It is fun, people are happy and cheering and nice to everyone around them. And they tend to go get a drink after the game...
It doesn't matter if he went to that school or likes American football, if his goal is to meet women.
Weekend races---I bet lots of women attend, just for chance to meet guys.
Trick or Treat night---PERFECT place to meet single moms, who are looking for men. If he took his baby there, and gave his ex-gf the night to go party with adults , she'd love it. And he and his baby would meet lots of new women.
But the sad truth is , he was not looking for a new girl friend. He was hunting for a victim, in my opinion.