The reason the boss is keeping her late is to stop OP from following her out at the end of her shift. He can tell OP is a creep

First Op is insane. He cannot get the income of someone who is not married to him. He is insane.

If he's a pilot, I'm an astronaut because I love space. I have spent so much money on games and simulations. I am also a detective because I am really into true crime and forensics.

In the last one OP said she was the kindest most wonderful person, but he didn't trust why she cut off her family.  He should have trusted her or made her aware of what his mother was saying.  OP's fiancé might have told him on her own before her family got involved.  OP's fiancé might not only hate her brother/family for how he got away with the crime and the tragedy that happened as a result, but she might also mistakenly feel responsible for the friend's sister taking her own life.

Most people don’t cut off their entire family for no reason. What gets me is how dare his mother say it was so long ago and everyone should move on. You think that girls parents just "moved on"? Not a chance.

I wonder the second story is an example of a classic “creepier seeing how he wants to see it”. For example, due to a new manager and that one being a little more firmer with OP, OP takes that as a threat and tries making it so the manager is the main issue. That the manager is the problem and everyone else has to see that.

And he can’t fathom the idea that the workers find him creepy and uncomfortable so they try reporting on him to the manager when they can (or just let him know that OP doesn’t buy their products often). It MUST be someone else who is causing this issue not him.

Thats just how I view it tho.

People in that last story is why SA is as rampant as it is. The fiancée should run, never look back and live her best life free of all of these sickos.

He knows full well why his wife is mad and hurt. He just genuinely doesn't care and pretends he doesn't understand.

13:52 This guy calling himself a pilot reminds me of the wives of officers when I was in the Army expecting us to address them by their husband's title, when they were not in the military in any way, shape, it's form. Must of then didn't work at ALL outside the home. Yeah, I will not be doing that. Nor will I be calling this man who has never been behind the switches and levers, a pilot.  Also, I appreciate your "stolen valor" comment.

I too am a pilot, because ive seen all 26 seasons of air crash investigations.

35:35 "Tell me what I should do to make her forgive me."
Ohhhh no no no no, you can't make someone forgive you, that's not genuine forgiveness. It should be "tell me what I can do to possibly earn her forgiveness".

The SA story was devastating for the fiancée. How dare he. The betrayal.

"She hadn't seen her family in years. In my family, that's considered a red flag"

EXCUSE ME WTF!!?? IN WHAT UNIVERSE IS THAT A RED FLAG!?

The last story makes me so livid. Like, people don't just cut off family for funsies, and OP doing ALL this BEHIND HER BACK then AMBUSHING her? Her reaction was entirely reasonable. For me, the trust would be gone. You are no longer a safe person. You didn't respect her enough to trust her judgement and forced her into an unwanted situation, much like what her brother did to her friend all those years ago. As much of a poison tree his mum is, hes ultimately a grown ass man and stuck around fully cognisant his partner would not be on board.

Im furious on her behalf and I hope shes doing well.

I mean the guy literally said he bought his wife out of the house so why the fuck does the wife owe him anything

I can't stand parents that crave grandchildren. If your child ends up having a child of their own, great! But you can't demand or expect for that to happen.

The pilot story OP sounds like a character on a sitcom.

The last one broke me.  I was SA'ed as a child by my father and I've never moved past it.  I've tried but it's hard to trust someone when one of the people who should have loved you most in the World destroyed your life like that.  The fiancé has every reason to react the way she did because the loved one of someone she loved was so destroyed she took her own life.  The brother not only got off scot free, he seemed proud of what he did.  The family didn't care and should have reacted like OP's fiancé if the brother/son had no regrets about what he did.

Contacting your partners family they’re no contact with just spews a tremendous amount of privilege. For me I automatically assumed her dad or sibling SA’d her and the fact that nothing like that popped into OPs head is wild and shows how out of touch he is.

35:26 Yeah... I wouldn't speak to my ex fiancé ever again 💀