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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.

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.