While I’ve been watching your weekly videos for a bunch of years now (sooooo enjoy them and they're spot on and chock full of great practical advice), I think this might actually be the first time I disagree with your opinion about giving compliments. I get how in theory it seems best to stick with things people choose, I STILL think it’s cringy (from a man or anyone else) to compliment people on their clothing, shoes, earrings, etc. when it has nothing to do with the content of the conversation you’ve shared up to that point. Not only can it come across as disingenuous (depends upon the style of delivery), but a compliment out of context like that just makes it seems like someone wasn’t really listening to what I’ve been saying. I’d say keep your compliments to the discussion at hand, about what you hear and think rather than about what you see.
That is actually a really great point and I completely agree with you. If I had been having a conversation with someone, and they shared things with me I agree that it would feel totally weird to just complement their shoes or something at the end of the conversation versus talk about what was talked about. I realize upon reading your comment that I would never do that and it makes total sense and it's very insightful. I'm really glad you said this because you're right! :)