My boss laughed and said, ‘I sometimes forget that I own a boat.'"
And there were so many frustrating responses!
Here are some of the top-voted answers:
1.

A husband and wife were at the table.
I picked it up and poured the wine, dribbling blood all over the white tablecloth.
Went outside, had a smoke, and thought about my life."

u/SleepyCountingSheep
2. u/BopbopHereWeGo
3.
In fact, the opposite is more likely.
“Built a $3 million house for a couple.

We have a joke going that we call it the help’s house.’
Now, this was still a $750k1 million home, no less.
Just struck me as not very grounded .”

u/nlights999321
5.
Someone else was going camping, and another guy was taking a long weekend to help his brother move.
He said, ‘You guys have no idea what vacation means, do you?

“He got real upset when I asked him where he was gonna work when he came back.
He didn’t last long.”
u/subtxtcan
6.

“‘I have no hair on my body!
You should have your husband take you to get laser hair removal!
It only cost me $10,000.’

Maybe in my dreams.
She was the mayor’s daughter, and I was catering her dog’s birthday party.”
“Me: ‘Yeah, I love flying.
I have a nice flight simulator setup at home.
Wish I could do it for real.’
Owner of the company: ‘Yeah, the real thing is so much better.
You should buy a plane.
I love taking mine out for trips.’
Me: ‘You sign my checks.'”
u/Jefe_Bezos
8.
I told him how much I loved the car and dreamt of owning one someday.
The owner looked at me confused and said, ‘What do you mean?
We sell them right here, you know?’
u/tbh3900
9.
“They lived in Boston, and we were talking about how small condos are there.
“My boss is an attorney.
Laughing somewhat ruefully, she said, ‘I cant believe I forgot to include that.’
The client and I quietly locked eyes with a shared understanding of how out of touch that was.”
u/headcase-and-a-half
11.
“l worked for Medicaid.
‘My, that was SO difficult!’
No duh, pal.
That whole idea pissed me off so bad.”
u/Nanatomany44
12.
“‘You’ve never been to Disney?
Did your parents not love you or something?’
Um, my parents were raising three kids, working two jobs on poverty wages.”
“Boss: ‘My wife and I decided that you and your wife should join us in the Caribbean.
I’ll pay for everything.’
Me: ‘We appreciate the offer, but we won’t be able to afford it.’
Boss: ‘Why?’
Me: ‘I’d have to hire someone to watch the kids.’
Surely your nanny can handle that!'”
u/nobody2u
14.
When I went to visit him, I showed up in my grandpa’s old Ford F150 truck.
He asked me why I drove around in that thing.
I shrugged and said, ‘Because I’m poor.’
And he said, ‘No, you’re not.’
It was like I ruined his whole hipster aesthetic, and he realized I wasn’t grunge.”
u/char-le-magne
15.
“‘How often do you go sailing?’
Said by a guy who knew I was struggling financially.”
I pointed out that most of us had budgets, and hostels were cheaper.
The thought had just never occurred to him that we couldn’t all afford that.
Same thing with restaurants.
He just never considered that nicer places weren’t in everyone’s budget."
u/Waste_Coat_4506
17.
“I was venting to a schoolmate about not being able to have a car.
She said, ‘Why dont you just ask your mom?’
It literally broke my brain.
Like yeah, why didnt I think of that?”
u/batphomet_
18.
That day, I’d had to take four showers to feel just a bit refreshed."
“‘You’re just letting money stop you.’
Yes, it does that.”
u/BriRoxas
20.
“I worked for a very wealthy lady.
Her son graduated college, and she put him to work answering phones.
She also bought him a car.
‘Can you believe it?
I told her I wanted a blue car.’
She didn’t get him a blue car, so he asked her to paint it.
I could see his naivete as he spoke since he truly thought this was something I could relate to.
I don’t know why more people don’t do this.”
Note: Some responses have been edited for length and/or clarity.