I (36F) have been friends with a guy (48M), we will call him Rob, for years. He’s a very wealthy and successful guy, does very well for himself, and has no kids, never been married before, etc.
He is a serial dater and his goal is to date the hottest girls he can. He spends sometimes thousands on them every week in buying them gifts, dinners, and straight up giving them cash.
It’s his thing and one of the ways he likes to spend his money. Whatever floats his boat, his life, his money, I don’t judge and if he’s happy then I’m happy for him.
However, recently, he went through an awful breakup that sent him spiraling and I was there every day and night to talk to him on the phone, offer him advice, read his sometimes over a hundred messages a day and otherwise console him.
We’re talking hours every day that I was spending on him and it went on for weeks. Quite honestly, it was exhausting after a while and there was definitely a lot of trauma dumping going on.
I am a single mom who works full time and I don’t always have a lot of free time or mental energy but I did my best to support him.
He recently invited me out to dinner saying that he “owes me” for all of the support I’ve given him, so we went out to a really nice restaurant and had a nice dinner, until the end.
The check arrived and he stated “Alright, we’re splitting this thing.” I was shocked, as he wanted this dinner and invited me!
When I questioned him and also informed him that I had to pay $100+ to a babysitter to be able to go out with him, he insisted that he’s not paying for me, that we are just friends.
I’m able to support myself and my kids obviously but going out is a treat because of how costly everything gets, $100 is a lot for me.
I sent him my half and left shortly after, somewhat upset, as I felt blindsided by this and also felt that he should’ve treated, given the fact that he invited me and also because he makes exponentially more than me and knows my struggles sometimes as a single mom.
tl/dr: Wealthy friend made me pay half of the expensive dinner bill even though he invited me to the dinner and he knows what a financial burden it is for me to go out.