I don't know what's with me and certain situations but I end up being far too often politically incorrect than otherwise. But these being tricky situations, there is no set answer to the same question.
For instance, if you bump into a cheerful looking acquaintance at a party and ask "so where's the boyfriend" and if pat comes the reply "oh we broke up", how are you supposed to respond? I've tried "oh i'm so sorry" and I've gotten "yeaa it is what it is" and then awkwardness followed by a sad face that I contributed to. I've also gotten "don’t be sorry coz i'm not" which I have to admit is a little hard to respond to except for an "alright then''. And then there's an occasionally narcissistic "he didn't deserve me" where I have to chime in and say "you bet" or something. Maybe I should just stick to the standard boring "so how are the Angels (or whatever her fav team is) doing this season?"
I'm bad with names. Rather I'm bad with names of important people. On my graduation day, I introduced one of my profs to my dad saying "this is professor" and then I shut up coz I couldn't remember his name. I didn't know his first name and couldn't recall his last. The prof didn't help out by finishing the sentence for me. So we all stood there in utter silence. Unfortunately, it has happened more than a few times. It's started happening in management meetings now. "On that front I'm working closely with" followed by stuttering or stammering in the first or last name if it isn't someone from my dept. Of course I remember the names of all 400 kids I went to school with.
Much like Meg Ryan in 'You've Got Mail', I can rarely reciprocate the kind gesture when someone's really mean to me. Then after the steam has evaporated and the season has changed, my mind is still thinking of a fitting response and a week later, I have it. At which point it’s always a day late and a dollar short. Totally irrelevant. But since it has taken me a week to frame the response, I have to do justice to it. It doesn't only end up being completely inappropriate but rather makes it sound so absurd. I'm getting better at it though, much to the annoyance of a lot of people.
Or when someone asks me if I'm ever gonna have a second baby... and I always end up going down the path of "Certainly, just so my first born can have some company and I won't have to be her best friend and actually get some peace of mind" and I'm the only one laughing while people are shooting me the 'you are so mean' look. I need to stop hanging out with single peeps. What do they know!
Maybe they offer courses on it in shady personal development institutes that I used to mock. I probably need one.