A lot of engagement stuff is so bonkers.
My dh's best mate has my favourite judgy engagement story ever :)
When I got together with dh, and met his friend and gf for the first time, she told me that night that she thought he was going to propose. I asked her what made her think that and she said 'because I told him to' 
He'd been carrying the ring in his pocket for two weeks (!) and had shown literally everyone we knew, barmaid in pubs, you name it, all the while she pretended not to know. Eventually, on NYE that year, he took her to central London with the intention of proposing at midnight on the bridge. However, she had grilled me and dh on his intentions and was not happy as it wasn't what she had really wanted. She had dropped hints to dh to try and dissuade friend from doing it 
Midnight approached and she 'had a panic attack' as she said she thought there would be a bomb on the bridge and made a huge fuss. So he missed midnight. About an hour later they were sitting on a bench on the south bank, alone, and he did it then. She accepted, called us to tell us (no, really!?) and all seemed fine. They had a really awful engagement party in central London with a James bond theme, she employed me to make her a bespoke dress (like Vesper Lynd), there was a gift list and he made a speech about how lovely she was (which I know she wrote most of). It was deeply cringy. She dieted especially for the party as they had a professional photographer
A month later, she called me and asked me if she could come over, and could I make sure dh was there, but not to tell her fiancée. She basically told us that she hated the way he had proposed, and couldn't live with it, and could we intervene and tell him to propose again, in the following manner: on a blanket (which she had brought to give us!) in her parents back garden, under the stars, with champagne. She even had a plan for me to 'secretly' get hold of her engagement ring so he could give it to her again.
She'd made a cd of 'appropriate music'
After she left, dh and I were gobsmacked. Friend had put a lot of thought into trying to make a proposal she would remember. She was upset as she didn't feel it was special or personal (?) enough, and that because she was in winter gear (for December midnight on tower bridge) and she wanted to be wearing a specific outfit she'd chosen, and that it was not the date she wanted... Etc etc.
We never said anything to dh's friend. He'd have been heartbroken. They split up a year later after a year of massive bridezilla-y behaviour including plans to ride into her wedding on a white horse which were scuppered as she could not find a horse which was 'white enough'.
Dh proposed to me on the sofa, in my slobs, one Sunday morning. We got married a year later. Couldn't tell you the date of the proposal for my life, nor the actual words he used. We'd discussed wether we wanted to get married, but never actually agreed to do it until that morning. He had a ring (very lovely) and we didn't tell anyone we were engaged for two weeks as I was in the middle of finals and woefully underprepared and we didn't want endless phone calls distracting from that :) I passed, we told our families, that was that, really. I'm not sure why it's something I was expected to want everyone I've ever met to be interested in, frankly. :)