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Friends: 10 Worst Dates In The Whole Series, Ranked By How Awful They Were -BB

Friends is a gold mine when it comes to awful dates. Whether it’s the gang messing it up for themselves, or it’s the gang sticking each other with bad blind dates, Friends never fails to deliver the most uncomfortable and hilarious moments.

From Ross’s paleontologist date that turns out to be a major slob who can’t find her hamster to Chandler’s date who stole his clothes and left him naked in a bathroom, this list has all of the most horrifying dates that Monica and the gang have ever experienced. Here are the 10 worst dates of the entire series, ranked.

10 The One Where Monica Dates Chip Matthews

Remember when Monica got a lipper from Chipper? She was pretty excited about scoring a date with Chip Matthews, which is understandable, considering it’s something she’s wanted since high school. Unfortunately, that’s also why it’s so devastating when this date goes horribly wrong.

Monica learns that Chip is severely stuck in the past, he still works at the same movie theater he worked at in high school and he’s still best friends with the same old popular crowd. The only good part about this date is that Monica realizes she was too good for the Chip Matthews type all along.

9 The One Where Ross‘ Date Is Messy

„Did Homo Erectus hunt with wooden tools?“ this is the question that Ross asks his perfect paleontologist date just before he learns the horrible truth – she’s extremely messy. This doesn’t sound like a big deal, but this girl definitely takes messy a brand new level. Her entire apartment is trashed and she’s not even sure where her hamster is.

Ross tries to convince her to come back to his apartment but ironically enough, she thinks Ross‘ place has a weird smell. Ross is insanely awkward whenever he’s at her apartment and even almost killed her hamster, luckily it turned out to just be a rat.

8 The One Where Phoebe First Meets Mike

Joey actually did Phoebe a huge favor when he procrastinated finding her a blind date and ended up choosing someone at random from Central Perk. Of course, this made for a pretty awkward double date between Mike, Phoebe, Joey and the blind date that Phoebe had actually carefully chosen for Joey.

Mike and Joey had trouble keeping their stories straight, no surprise there, and Phoebe found out that Mike was actually just a stranger and Joey didn’t handpick him for her at all. Even though Mike and Phoebe’s first date went horribly, it was all ultimately for the best because Mike and Phoebe are definitely meant to be together.

7 The One Where Ross Wears His Leather Pants

This is definitely one of Ross‘ worst dates, to date. He’s convinced that his leather pants are really cool so he wears them to a girl’s house. Of course, they’re really uncomfortable and hot so when he goes to the bathroom to take them off to let his legs breathe, he finds that he can’t get them back on anymore.

Ross then calls Joey for help and Joey tells him to use baby powder and then lotion to try to help get the pants back on. The paste doesn’t do the trick so Joey advises him to make him himself a pair of „paste pants“ and then he hangs up the phone. Poor Ross.

6 The One Where Ross Whitens His Teeth

It only makes sense that Ross would be at the center of most of the horrible dates on the show. This time he’s sporting his newly whitened teeth where he left the teeth whitening gel on for an entire day longer than he was supposed to. Ross tries everything from wearing different colored shirts to putting on makeup but nothing hides his crazy white teeth.

When it comes time for his date, he’s able to get by for a little while without her noticing, at least until they turn off the lights. It turns out Ross’s date has a black light (even though it’s 1999) so when the lights went off, his glowing teeth really freaked her out.

5 The One Where Chandler Is Stuck In The Bathroom

Apparently Chandler had this one coming, but it still seems a little harsh. When Chandler starts dating Susie, he thinks she’s his dream girl. Unfortunately, it turns out that she was only dating him as a scheme to get back at him for raising up her skirt and showing everyone her underpants in the 4th grade.

Chandler didn’t see this coming so of course, he let her talk him into taking his clothes off in a restaurant bathroom, where she then stole his clothes and abandoned him, leaving him naked in the bathroom.

4 The One Where Rachel Goes Out With Joshua’s Parents

Ah, „The One With Rachel’s New Dress“. This episode will always be hilarious. When Rachel and Joshua end up at his parents‘ house one night, Rachel changes into a dress that’s more along the lines of lingerie, thinking that it’s just she and Joshua at the house.

Of course, Joshua’s parents return home early and awkwardly find Rachel in this dress. She tries to play it off like it’s all the rage in fashion, even though it’s obviously lingerie. Refusing to admit embarrassment, she even agrees to go out to dinner with Joshua’s parents right then and there, in her „high-fashion“ dress.

3 The One Where Ross and Rachel Go On Blind Dates

This one is kind of an obvious one, but it’s for that very reason that it’s so high up on this list. Phoebe and Joey purposefully set Ross and Rachel up on horrible blind dates, thinking that it might encourage them to get back together.

Ross gets stood up and Rachel’s date is Steve, the strange food critic that got high when he was supposed to judge Monica’s cooking skills in season one. He’s pretty memorable, but not for good reasons. Needless to say, these blind dates were awful.

2 The One Where Monica Dates Young Ethan

Monica is pretty creeped out when she finds out that her date Ethan, wasn’t even alive during the bicentennial. After already being with Monica, Ethan reveals that he’s actually a senior in high school. This is pretty disturbing for everyone and definitely one of the worst dates of the entire series.

Ethan should have come clean to Monica about his age, but also, how were there not any signs that Ethan was only 18? At least the gang found this hilarious and got some pretty good Teenage Mutant Ninja Turtles jokes out of it.

1 The One Where Rachel Is Over Ross

This is the best worst date of the entire series. Not only was it extremely cringe-worthy, but it was also pivotal to Ross and Rachel’s relationship. Rachel goes on a date after she finds out that Ross is going to be getting a cat with Julie. She can’t think about anything except for Ross the entire date, so she gets visibly drunk and ends up leaving Ross a voicemail explaining how over him she is even though Ross didn’t know she was ever „under him“ to begin with.

While this date is really awkward for everyone, considering Rachel’s date hates her and she makes a random guy at the restaurant give him her phone, at least this date finally ushered in the age of Ross and Rachel.

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