Todays Journeys Through Awkwardtown

Teaching your parents what "tea-bagging" is. (In reference to what drunk fraternity boys do to each other when one of them passes out.)
Asking a client on the phone, whom I've never met, what his spouse's name is, for insurance purposes only, to which he replies, "Well, you've made me wish I wasn't married. You sound attractive."
Answering the phone when an ex-boyfriend's (for lack of a better term) new wife calls. She's 48. I'm 23. The same new wife who told my parents that her husband and I were friends on Facebook. As if it were some sort of crime. The same woman who I grew up knowing as a friend of my parents'. I was in children's church with her kids.
Debating what the term is for how many-times-you-have-to-push-before-your-baby-is-born. With a marketing rep who can say anything and I blush (Why? I still haven't figured it out. I don't find him attractive. Maybe it's his confidence?). He calls them "reps". I think that sounds like a work-out.
Saying "yes sir" and then realize you're talking to a woman.