She swore off seeing him again after he kept her waiting 20 minutes on first date — then his message two days later asked a wild question
We’ve all heard our fair share of dating horror stories, but now and then, a bizarre one comes along that completely takes the cake. In a video shared by Instagram user Sammy (@sammy_rid) on Tuesday, March 31, 2026, she described showing up on time for a 9:30 p.m. date, only to find out her date hadn’t even left his apartment yet. What followed was a string of delays and awkward moments that quickly went beyond just being late. And a couple of days after the disastrous date, he asked her a question that left her completely baffled.
What started as a simple delay quickly turned frustrating as he kept extending his arrival time. After waiting long enough, she chose to leave and was convinced he wasn’t prioritizing the date at all. But he remained persistent, calling her repeatedly and urging her to come back, even trying to track her down. So, against her better judgment, she met him once more with the promise to never see him again. Then, a few days later, after no contact, he sent a message asking, “Will you be my social media manager?” which left her stunned. Safe to say, it wasn’t the follow-up she or anyone would expect.
When she left the restaurant after waiting for him for 20 minutes, he even showed up at the train station trying to find her in order to "fix things." As he finally managed to speak to her, his reasoning only made things more confusing. He kept insisting she come back, saying things like “What if you’re my person?” This felt far too intense given how the evening had already unfolded. She then agreed to see him again after 30 minutes at a place close to her house. In fact, the meeting itself was brief and awkward, and the staff also picked up on the uncomfortable energy. The bartender kept asking her if she was okay, which gave everyone the idea that the man was acting strange from the get-go.
The comment section was enraged for all the right reasons. @kayliemurphy noted, "If he were your person, he would have been on time or let you know." Meanwhile, @darbyhonea remarked, "Dating in this city tests me every single day, because, what do you mean social media manager?" Some even shared their own bizarre dating stories, like @savannahlaurenphoto, who recounted, "One time a guy ghosted me and then three weeks later he hit me up because he found his old comedy notebook and wanted to test out his jokes on me." At the end of the video, the creator expressed her need to take a nap, showing how exhausted she was from the entire encounter.
For more such videos, you can follow @sammy_rid on Instagram.