A cultural phenomenon when it first aired between 1994 and 2004, there had never been a sitcom quite like Friends. The series featured six, well, friends, living and loving in New York, but it didn’t always produce timeless comedy gold. These are the Friends moments that make us cringe today.

For sitcom fans working their way through every episode of Friends and haven’t finished yet, spoiler alert: Monica winds up with Chandler. But before that crucial pairing is locked down, Monica dates a lot of guys, the way a woman in her twenties is wont to do.

One of her boyfriends is Ethan, a guy that seems younger than Monica. How much younger? Well, he tells Monica that he’s a senior, which she takes to mean “senior in college.” Ethan also reveals that he’s a virgin, but after they sleep together for the first time, as in his actual first time, he admits that he’s not a senior in college, but a senior in high school.

Having participated in an encounter that would make her, as Monica says, a felon in 48 states, it’s not surprising that the official title of this episode is “The One with the Ick Factor.”

Watch the video for more Memorable Friends Moments That Make Everyone Cringe Today!

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Monica dates a teenager | 0:17
Not so friendly to alcoholics | 1:08
Chandler goes catfishing | 2:23
The naked truth | 3:35
Joking about gender | 4:44
Giving up the dream for Ross | 6:06