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She Went On Two Dates With Guys Who Ended Up Being Best Friends, And One Sent Her A Venmo Request For Dinner And Drinks

profile Emily Chan | Feb 18, 2026
Feb 18, 2026
Close up of pretty brunette woman in
Akaberka - stock.adobe.com - illustrative purposes only, not the actual person

Dating app drama is a thing, but sometimes, it doesn’t start until after the first date. If you’ve ever dated in New York City, you already know the odds are wild.

In 2021, TikToker Vivi’s (@viviarmacost) best friend downloaded a dating app for the first time and went on two dates in one weekend with two different guys who ended up being best friends.

They were 25 years old, and she was 21, still in college, and had an internship in the city.

You’d think the chances of accidentally going out with two best friends back to back would be slim in a city as big as NYC. But the dating world can be shockingly small.

Right after both first dates, she politely told them that she wasn’t interested in pursuing a serious relationship with either of them. Apparently, that did not sit well with them.

They responded with long, defensive messages that veered straight into insults. One of the guys attempted to take her down off her high horse, even though she wasn’t even on one.

“I’m a little confused. You went on a date with my best friend the night before and gave him the same response. Probably why it was hard for you to recall messages we sent back and forth. Not sure if you’re looking for validation or what. You’ve probably been on dates each day this week and certainly are not pretty enough to be pulling that…so knock it off and grow up.”

He proceeded to send her a Venmo request for her share of dinner and drinks, which was around $40. The second guy was no better.

He wrote in a similar tone, which begs the question: Did they come up with these texts together?

Close up of pretty brunette woman in cafe of asian cuisine. Woman looking at camera and smiling.
Akaberka – stock.adobe.com – illustrative purposes only, not the actual person

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“So, I’m a little confused here. My best friend from high school took you out the next night and got the same exact message I did. You’re a pathological liar, and it’s honestly pretty pathetic…If you’re not pretty or cool enough to get guys to get you free drinks, don’t make up all those lies and use people to get them. It reeks of desperation and pity.”

He ended his text by stating that he had more respect for “people standing on a street corner doing the same thing she did.” The irony is that one of the guys had actually asked Vivi’s best friend not to go back to college and stay in New York to continue dating him, even though it was their first time meeting.

Vivi says the text messages were so over the top that she couldn’t help but laugh. It seems that the only thing more fragile than a first date is a best friendship tested by the same polite rejection text.

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By Emily Chan

Emily Chan is a writer who covers lifestyle and news content. She graduated from Michigan State University with a degree in... More about Emily Chan