When 25-year-old TikToker Caitlin shared the story of her “worst first date ever,” it quickly struck a nerve online. Her Aug. 14, 2025, video, which now has more than 365,000 views, detailed her night ...

Oh no, that’s bad. Dating in today’s digital age is no easy feat. And while it’s normal to have the occasional bad first date, one Gen Z woman’s recent experience with an “egomaniac” almost twice her ...

From awkward silences to shocking surprises, these terrible first dates are filled with cringeworthy moments and unexpected drama. If you love real-life dating fails, relationship disasters, and ...

The majority of first dates are dreadful: Your dumb jokes backfire, the filet comes overcooked, and your eyes start to hurt from so much awkward staring. But there are bad first dates, and then there ...

I have this friend who, when I'm feeling fatigued or intimidated by the prospect of swiping right and going on another <a href="https://www.menshealth.com/sex-women ...

Ever been on a bad first date? You’re not the only one. In this episode of Color Me Yours, Gwen and Bayley ask people what their worst first date has been, and what their idea of a perfect one is. If ...

Terrible chemistry, major red flags, and first dates that should’ve never happened. 'Stunned' Lamar Jackson not ready to talk ...

Caitlin’s date checked all the bad first date boxes and exhibited red flags, including but not limited to: using her as a prop, revealing that he’s incapable of dating women his own age, threatening ...