Hmm. It never seemed to in my case. It led to conversations about how well I knew these people, or whether it was appropriate to leave them, or why I didn't get a family member.
And really, the tone of voice was sort of snotty.
As a simple conversation starter, it was really annoying. It was sort of, "Oh, there you are, are you handling your responsibilities properly."
You wanna make conversation? Ask me how my kids are. How my job are. How the transition to parenting is.
I *got* the kinds of questions that were true curiosity from a peer about how I'd handled the babysitting question. You could tell the difference.
I have a friend that was flat out told she was irresponsible for having a non-family member babysit the kids. She shot back that statistically the kids were safer with a stranger off the streets than with family. The kicker was because of trust and abuse issues there was no way her kids would have been left alone with that branch of the family.
2x since I moved back home I've had the a conversation like this
Friend: Introduces me to someone using our full names
Other Person: Blinks makes polite noises
Me: I reply
Other Person: Ok this is going to sound crazy but did you grow up (either in Memorial or on my childhood street)
Me - Yes
Other Person - I babysat you - you are allergic to peanuts
Part of my Dad's job was to eat out pretty much every Friday and Saturday night at one of the restaurants his business sold beer to. He and Mom would go out on a date night on Fridays, and we would go out all together on Saturday. So they used a LOT of babysitters.