Pardon my french, this story is 100% true and I was there to witness the whole thing.

I'm sitting with my mates playing poker the other night, and a few older gentlemen were present, mainly my co-workers and my boss. The game progresses until we began discussing where we all used to live (forget how it came up, that's irrelevant). Someone asks my buddy "mate, why did you move here? where were your parents from?". My buddy answers in kind and sure enough my boss goes "I used to live in X and grew up there, what's your mom's name". My buddy replies "ahh it's Jane Doe". My boss immediately smiles and goes "I used to know her pretty well... you should ask her about me". My buddy just goes "oh and did you know her twin?" and he replies that he knew the whole family.

At this point I caught on that Mr. Boss over here had banged my buddies mom. My buddy might have too, as he just was like "oh god, this could be awkward". Mr. Boss goes "yeah, is your mom retiring this year? I ran into her a few months ago". My buddy agreed she was and that was the conversation.

Anyway, I had the privilege of crashing at my friends house last night, who still lives with his parents. Unsurprisingly, his mom made everyone breakfast this morning (It's a jewish holiday, they are jewish). So, everyone, mom, buddy, his dad and his sister, and my self are sitting at the table eating some pancakes. Buddy goes "ay mom, do you know Mr. Boss". She goes "Mr boss?!?!, yes he was the first guy I ever liked, that's how I got the huge scar on my leg from his motorcycle"

I kinda felt awkward because his dad was at the table. She goes "wow, that's a blast from the past, what did he say about me" and my buddy was just like "oh that he knew you and your family from back in the day when you lived in X". She was just like "oh, well yeah I was in 9th grade and him in 12th"

Now, she didn't come outright and say "yeah I fucked him a ton" nor did she say "I lost my v-card to him". Nor did she really do anything totally inappropriate (IMO - we've all had first likes). But between the way Mr. Boss responded and the way his mom responded I think it's almost certain he was railing her out. Also mildly interesting (to say the least) that he knew she was retiring this year, and knew the company but not the position that my buddies dad held. Maybe she just forgot that they had ran into each other a few months back, but perhaps there's something more sinister there - I'm not sure.

Buddies mom is probably an alpha widow who I've heard making jokes about how she dated a lawyer for "like 10 years but he was a asshole" and never got married to him (in relation to my buddy being a 3rd year law school student). She had my buddy at about 35 (I figured this part out from Mr. Boss's age) and works as a secretary. Overall, I'd say that buddies dad doesn't do bad, is a manager for a large company and overall seems pretty "alpha" which is why it's kinda confusing that he choose to marry her. I've been around their family long enough to know he's indeed the captain who makes ALL of the decisions, he does yard shit and she does ALL of the house work 95% of the time. Ironically, out of all the conversations/dinners/golf I've never heard him talk about other girls other than straight up saying how hot most young girls are these days. (which we always giggle at).

My point: a girls past does matter. My buddy seemed a little uncomfortable with the whole situation which he later confided in private to me. It's going to suck for him if Mr. Boss starts telling other co-workers (who are his friends too, our age) about this.