20 'Friends' Dates Way More Awkward Than Your Last Tinder Meet-Up

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Amid the many pure, romantic moments throughout Friends' 10-season run, there are just as many horrifying, bizarre, and awkward dates sprinkled in. The weirdest dates on Friends are a stark reminder that there weren't always grand gestures and candlelit proposals in store for Phoebe, Joey, Ross, Rachel, Monica and Chandler. They had to weed through plenty of duds to get to their respective happy endings.

It's easy to forget all the gang endured before things ultimately worked themselves out for the best. One of the biggest themes in Friends is growing up and finding your place in the world, and to do that, you often have to cross paths with a few people that aren't your meant-to-be.

Before Ross and Rachel decided they were soulmates once and for all, before Chandler and Monica tied the knot, before Phoebe and Mike had that snowy wedding in the streets, they all sat through their share of uncomfortable dinners. They encountered everything from totally unstable creeps to simple misunderstandings that spiraled out of control, and the ensuing events range from hilarious to downright uncomfortable. So, for the sake of making us all feel better about our own awkward dating experiences, let's revisit some of the most memorable, ill-fated romantic outings on Friends.

1. An Inappropriate Sibling Mixup — Season 1, Episode 5

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In an effort to get back together with an ex, Joey plots to set up the woman's new boyfriend with Monica. The catch? Joey tries to keep his plan a secret by telling Monica that his ex and her new man are siblings, making all their romantic interactions look seriously inappropriate.

2. Ross Can't Talk Dirty — Season 1, Episode 15

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Ross is making out with a new love interest after a date with relative ease before she makes a request: she wants him to talk dirty. The results are... less than sexy.

3. Rachel Is "Over" Ross — Season 2, Episode 7

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At this point in the series, Rachel is hung up on Ross, who's currently dating Julie. Ross is blissfully unaware that Rachel ever had feelings for him, but that all ends when Rachel drunkenly steals a cell phone — in front of her date! — and leaves Ross a game-changing voicemail.

4. Monica Realizes Why Fun Bobby Is So Fun — Season 2, Episode 10

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One of Monica's earliest love interests is "Fun Bobby." Everyone loves him, but when he's her date to a dinner party, they realize that he might have a bit of a problem with alcohol. Not a great sign.

5. Rachel Dates Someone Too Familiar For Comfort — Season 2, Episode 10

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Generally, you want to stay away from dating someone who's a carbon copy of your old flame. Rachel didn't really heed that advice when she met up with Russ — a date who looked eerily similar to a certain someone in the gang.

6. Erika Thinks Joey Is Actually Dr. Drake Ramoray — Season 2, Episode 12

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This isn't the greatest look for Joey. He goes on a date with Erika, a clearly confused woman who thinks Joey is actually his Days of Our Lives character. He goes along with it for way too long, and it's uncomfortable to say the least.

7. An Old Friend Of Chandler's Gets Her Revenge — Season 2, Episode 13

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Julia Roberts guest stars as Susie, a childhood "friend" of Chandler's who's been holding a grudge for decades. Chandler lifted up her skirt during a play when they were children, and though she pretends to be over it long enough to get him on a date, she's definitely seeking revenge.

8. Charlie Sheen & Chicken Pox — Season 2, Episode 23

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Phoebe unfortunately has chicken pox during an ex-lover's visit to the city, turning what would be a romantic encounter into a medically questionable (and very itchy) visit.

9. Monica Dates Phoebe's Interpreter — Season 3, Episode 15

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When Phoebe meets a suitor who doesn't speak English, she asks Monica to come along and keep his interpreter company. Monica ends up doing too good of a job, because she and the interpreter spend the whole night talking, leaving Phoebe and her date unable to communicate.

10. Ross Stumbles Upon A Dirty Apartment — Season 4, Episode 6

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Ross is a notoriously uptight person, but nothing sets him off quite like arriving at his date's home to find it cluttered and filled with trash. Oh yeah, and she's missing her pet hamster somewhere among the rubbish.

11. Rachel & The Guy Who Loves His Sister — Season 5, Episode 10

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Rachel has her eye on Danny, a man in her building, for quite some time before meeting his sister. But when she realizes that the two of them are just a little too affectionate with each other for her comfort, an otherwise innocent coffee house get-together gives her the creeps.

12. Ross Wears Leather Pants On A Date — Season 5, Episode 11

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Who can forget the leather pants incident? One of the New Year's resolutions Ross comes up with is to do things he's never done before — like wear leather pants on a date. The ensuing calamity is hilarious and so, so unfortunate.

13. Ross Whitens His Teeth A Little Too Much — Season 6, Episode 8

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Everyone always wants to look their best for a date. Slather on that makeup, do up your hair, put on your best outfit... but maybe don't overdo it like Ross did with the teeth whitener. It's more scary than sexy when he meets up with his date.

14. Ross Dates A Student — Season 6, Episode 18

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Ross thinks that dating one of his college students is merely frowned upon, but as he soon learns when on a coffee date with Elizabeth, it's actually pretty concretely against the rules.

15. An Awkward Double Date With Elizabeth's Dad — Season 6, Episode 21

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Not only does Ross date his student, he also meets her father, played by Bruce Willis. Rachel wants to help Ross by talking him up to the skeptical older man, so the group goes out to dinner together. Ross, predictably, doesn't come away looking all that great.

16. Ross & Joey Pretend Not To Know Each Other — Season 7, Episode 17

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Joey and Ross are competing for the affections of Kristin, a girl who recently moved into their building. They set ground rules between each other to ensure they both get a chance to impress her, but when Joey shows up unannounced to Ross's date and they pretend not to know each other, things go off the rails.

17. Phoebe & Jim Definitely Are NOT Meant To Be — Season 8, Episode 17

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After seeing the same man all over the city, Phoebe thinks meeting Jim is fate. He's charming at first, but he very quickly turns into one of the creepiest people to ever appear on the show. Run, Phoebe!

18. Joey Introduces Phoebe To Mike — Season 9, Episode 3

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Phoebe and Joey are supposed to secure dates for one another, but Joey totally drops the ball and neglects to find someone. He pulls the name "Mike" out of thin air, finds someone with the same name at Central Perk, and it all unravels during their double date. Little did we know the romance that would follow.

19. Rachel's Self-Loathing Blind Date — Season 9, Episode 14

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Poor Rachel embarks on an innocent date with a self-deprecating Jon Lovitz. Amidst all the insults he lobs at himself, he soon reveals that he once owned a restaurant that he lost to drugs, and by the end of the date, he's weeping. Yikes. Rachel can't get out of there fast enough.

20. Ross Is Certainly Not "Fine" At This Double Date — Season 10, Episode 2

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A lot of people were skeptical of Joey and Rachel's relationship when it developed late in the series, but things were perhaps at their most awkward when Ross invited Charlie, Joey, and Rachel over for a double date at his apartment. He gets drunk, burns his hands on a scalding fajita pan, and is quite clearly NOT OK with what's happening.

This is just a taste of the delightful dating misfortune that befell our favorite characters over the years. Even if you can't relate to all the romantic faux pas they encountered, you can certainly laugh along as it happens.