So Saturday I got a text from my good friend of 40+ years. Last year, his dad passed away from effects from dementia. His parents are a bit younger than mine, I think his dad was only like early 70's and his mom is like 73/74.
To give a bit of context, me and my friend also roomed together in college. So we had a little bit of friction kinda at the end, but nothing real bad. He didn't finish school, but instead found a wife and ended up moving to where she's from and getting married. They've lived "away" from our home-town for the last ~25 years, so we haven't been super tight in this time but would get together every few years to go to a football game or just hang out.
Anyways, I've known him and his parents since at least the mid-80's. He texts me Saturday and said "Hey do you know this guy?". He's dating my mom...and he's 53.

Now, this isn't necessarily the same thing, but after losing my dad 6 years ago, my mom has had several boyfriends, but they were all close to her in age. And two of her BF we knew, one being a neighbor who lived several houses down, and one other guy being a dad to a friend of ours from way back. She's on her 3rd BF...but he's like 74/75. Mom is 78. So no age discrepency. For comparison, me and my friend are both 50. His mom is like 73/74.
So I look the guy up on the jail records and nothing pops up. I try different combinations of spelling, different approaches. Finally, I put his first name initial with a * after it and his last name. Holy shit...dudes got a criminal record a mile long. Multiple felony charges, DUI, assault, restraining orders...I sent this to my friend, who also tried to lookup his criminal record and he was freaking out. He said he looked it up and never saw anything.