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She Invited Him On A Surprise Date, Then Stuck Him With The $200 Bill And A Heartless Thank You

profile Bre Avery Zacharski | Apr 13, 2026
Apr 13, 2026
Young couple talking over a formal meal
dglimages - stock.adobe.com - illustrative purposes only, not the actual people

Who reaches for the check first can turn into an awkward dance that I think anyone who’s been on a few dates has encountered. But if someone asks you out on a surprise date without warning you that you’re headed to a restaurant where the night will cost you more than your last grocery run, is that fair?

For the last three weeks, this 27-year-old man has been dating a girl who is two years younger than him. So far, they have been out on three official dates.

The first two were pretty wonderful, and for their first date, they had coffee together. For their second date, they went out to dinner, and it was casual.

They ended up splitting the bill for dinner, and she didn’t make a fuss about it, nor did she make it seem like she expected him to pay for the entire evening.

“She seemed really down to earth, and we have great chemistry, so I was excited when she texted me saying she wanted to take me on a ‘surprise date’ this weekend to show me one of her favorite spots,” he explained.

“She told me to dress up a bit and gave me the address to this upscale rooftop lounge. I was thinking, okay, maybe she wants to treat me for a change, or it’s just a fancy place she likes.”

“We get there, and she starts ordering expensive cocktails and a few small plates like it is nothing. The vibe was great, but then the check comes, and it is over two hundred dollars.”

She stared down at the bill, looked up at him, and simply said thank you for taking her out on a date that night while smiling from ear to ear.

He was so astonished that he didn’t know what to do except pay the check without a fuss. He was not trying to create a commotion in public, and it was a very fancy place.

Young couple talking over a formal meal in a restaurant.
dglimages – stock.adobe.com – illustrative purposes only, not the actual people

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Since that fateful third date, he’s felt off about this girl. He thinks that if you go through the trouble of inviting someone out on a date and claiming it’s a surprise, you need to either pay for half or do someone the favor of informing them that it’s expensive before going.

“Now I am worried that she thinks I am just going to fund her expensive taste, especially since she is the one who chose the location,” he continued.

“I really like her, but this feels like a red flag regarding how she views money and effort in a relationship. How do I bring this up without sounding like a cheap guy who is counting pennies?”

“I just want to know if we are on the same page about how dating works.”

This girl took him for a ride, and her manipulativeness is not cute. She used him for her own personal gain, and I’m surprised she thinks she can go around treating anyone like that, let alone someone she’s dating.

I agree with him that it’s not fair or nice to tell the person you’re seeing that you have a date planned, only to leave them with the bill.

Sounds like she’s only out for his money or what he can buy for her, so there shouldn’t be a date four in their future. Back to the drawing board for him.

What advice do you have for him?

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By Bre Avery Zacharski

Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski