Argh, if this was 12 years ago, I'd be wondering if this thread was about me!
I used to do the bulk of DD's school drop offs / pick ups, I'm her Dad. I'm also spectacularly crap at small talk and found the playground excruciating. Would have been happy just stood on my phone like an antisocial gremlin but wanted to be sociable for DDs sake.
DP is effortless at small talk, so one evening I asked her how she does. She gave me a bunch of ways she starts conversation, one of which was complimenting someones hair, clothes etc. That one kind of stuck with me. I own a lot of geeky / funny t-shirts, and quite often strangers mention that they like them or that they're funny, and it sparks a conversation.
OK, I thought, I can do that. And off I go with my new conversational arsenal. Don't get me wrong, I'm not telling everyone I meet that I love their clothes, but it becomes one of the tools I used. Among others, I also started watching Gogglebox, so I'd be able to talk about TV that wasn't sci fi.
3 months on, things have gone swimmingly. I have actual playground friends. Probably more than I had when I was in school! DD is getting playdates, all is well.
Until one day when I'm talking to two Mums, we'll call them Jane and Claire. I mention to Jane that I like her top, and notice a weird look from Claire. Janes kid comes out and they leave, and Claire takes the opportunity to say to me "You and (DD)'s Mum are still together aren't you". I say "Yes, why?". "You might want to be careful, I think Janes getting the wrong idea."
I relay this info to DP that evening, and she asks what we'd been talking about. I tell her and she rolls around laughing.
I don't talk to women about clothes any more.