20 of the worst dates from “Friends” that hopefully won’t happen to you

With 10 seasons and 236 episodes, Rachel, Ross, Monica, Chandler, Phoebe, and Joey dated A LOT. Most of it happened between Seasons 1 through 5, because after that, everyone coupled off, had babies, and found Mike Hannigan.

Some of their dates were good. Some of their dates were bad. And then some of their dates went south very quickly. Here are the worst of the dates our Friends found themselves on (and may you never end up on one of these dates yourself).

Season 1, Episode 5, “The One with the East German Laundry Detergent”

Joey wants to go out on a date with his ex-girlfriend, but she has a new boyfriend, so he tricks Monica going into going on a fake double-date with him. Monica thinks she’s going out with the brother of Joey’s ex. He’s really her currently boyfriend. Confusing? Try being Monica, when she sees the two getting a little too cozy to be brother and sister.

Season 1, Episode 8, “The One Where Nana Dies Twice”

Someone at work tries to set Chandler up on a blind date. With a guy. Because, this is Chandler. This sends Chandler into a downward spiral, trying to figure out what everyone truly thinks of him (and why his coworkers think he’s into guys).

Season 1, Episode 14, “The One with the Candy Hearts”

Ross goes out on a date and runs into his ex-wife, Carol. It’s awkward, and even more awkward when he actually kisses Carol. But more importantly, Chandler’s infamous on-and-off again girlfriend, Janice, is first introduced, and they sleep together for the first time, and then Chandler breaks up with her (for the first time) on — wait for it – Valentine’s Day.

Season 1, Episode 15 and 16, “The One with Two Parts”

Rachel gets hurt, and ends up at the hospital. Rachel doesn’t have health insurance, but Monica does, and convinces her to switch identities.  That’s when dreamy doctors George Clooney & Noah Wyle — you know, from ER, so talk about NBC synergy — walk in to treat “Monica” who’s really Rachel. The girls do actually go out with them, still pretending to be the other. It doesn’t end well, because it never does.

Season 2, Episode 10, “The One With Russ”

Rachel is dating a guy named “Russ.” It’s just David Schwimmer, playing Russ. Rachel dumps Russ, because he reminds her for someone… she just can’t figure out who.

Season 2, Episode 12 and 13, “The One After The Superbowl”

Joey dates Brooke Shields! But she’s a crazy fan-stalker. Chandler dates Julia Roberts! But she’s seeking revenge for the fact that he wronged her in elementary school. Julia Roberts steals all of Chandler’s clothing, and leaves him naked in a bathroom.

Season 3, Episode 12, “The One with All the Jealousy”

Monica, throwing caution to the wind, dates one of the busboys at the ’50s themed diner where she works. He writes her a poem, but the poem is really about Phoebe. Because this dude has also dated Phoebe.

Season 3, Episode 15, “The One Where Ross and Rachel Take a Break”

Phoebe dates a diplomat and that’s awesome, except she needs a translator to go with them on their dates, because neither can understand the other. Monica falls for the diplomat, and then there’s a huge lost-in-translation miscommunication situation going on.

Season 3, Episode 19, “The One with the Tiny T-Shirt”

Monica starts dating Pete (played by John Favreau) even though she’s not attracted to him, and she finally tells him that she’s not attracted to him, but then they keep dating. It’s uncomfortable just thinking about it.

Season 3, Episode 22, “The One with the Screamer”

Rachel dates Ben Stiller! But he is a, uh, kinda intense bro, and instead of calmly talking through his feelings, he screams. And scares Ross.

Season 3, Episode 23, “The One with Ross’s Thing”

Phoebe tries to date TWO guys AT THE SAME TIME. And we all know THAT works out pretty well in the end! It would have worked out fine for her, but they both show up at her Central Perk set. The two guys realize she’s dating the both of them, and both break up with her. This is how it always works out in the end.

Season 4, Episode 2, “The One with the Cat”

Monica, completely transformed from high school, manages to get a date with Rachel’s high school boyfriend, Chip. Monica is loving it, until she realizes that Chip is stuck in the past, and even worse for Monica, still living at home with his parents. But he’s got a motorcycle!

Season 4, Episode 5, “The One with Joey’s New Girlfriend”

Rachel, in an effort to make Ross jealous, starts dating a much younger guy. Like, he’s still in college. Also, he’s stealing her cash and her belongings.

Season 4, Episode 10, “”The One with the Girl from Poughkeepsie”

Ross struggles trying to date a girl who lives really far away, and accidentally falls asleep on the train going to go visit her, and ends up in Canada. Only something Ross could do.

Season 5, Episode 10, “The One with the Inappropriate Sister”

Rachel’s dating this new guy, and she’s really into him, and he takes her to meet his sister. That’s when she finds herself kinda creeped out by the fact that this guy has a very close relationship with his sister. Maybe like, too close.

Season 6, Episode 8 “The One with Ross’s Teeth”

In the “Trying Too Hard” category, Ross over-whitens his teeth, and then doesn’t want to open his mouth, at all, in front of his date. Once again, only something Ross could do.

Season 6, Episode 22, “The One Where Paul’s the Man”

Ross and Rachel end up on an accidental double-date weekend getaway. Ross is dating this girl Elizabeth, and Rachel is dating Elizabeth’s dad (Bruce Willis). Remember: Elizabeth is the one who eventually will throw the water balloon at Ross.

Season 7, Episode 8 “The One Where Chandler Doesn’t Like Dogs”

Rachel hires an attractive new assistant at work, Tag, and then invites him over for Thanksgiving dinner.  Rachel’s got ~feelings~ for him, but isn’t sure how he feels, since Tag just got out of a relationship. Joey then accidentally slips and mentions that Rachel likes him. MEANWHILE, Tag’s car is being stolen. It’s a perfect storm.

Season 8, Episode, 12, “The One Where Joey Dates Rachel”

JOEY AND RACHEL DATE. THIS IS STILL WEIRD TO THINK ABOUT ALL THESE YEARS LATER.

Season 9, Episode 3, “The One with the Pediatrician”

The last and final Friends date is the best Friends date, because it brings us MIKE! However, it’s not smooth sailing to get to Mike. Joey failed to find Phoebe a date, so he walked into Central Perk, yelled, “MIKE?” and Mike Hannigan answers. He’s now Phoebe’s date, posing as one of Joey’s old friends. Sadly, he and Joey can’t keep up the charade, Phoebe finds out, and she’s pissed. Thankfully, in the end, she gives Mike a second chance, and the rest is Friends history.