There's a reason most of the Friends ended up coupling up with each other instead of continuing to brave the polluted dating pool that made their love lives so DOA before they lobster-paired off. Their tastes in significant others were abysmal (which, contrary to Joey Tribbiani's grasp of the English language, is not a compliment).
The Friends fam brought in a lot of trial add-ons -- half of which Ross may or may not have married -- but there were only a few that ever really stuck past the obligatory one-to-three episode run and fun arc, like Janice, Richard, Mona, and Mike Hannigan.
For the most part, though, everyone else they dated had a humorously horrid flaw and/or were just terrible people, and in many cases they also made the Friends foul right alongside them (especially when it involved Phoebe and her twin sister's slew of jilted lovers, VOM).
Here are our picks for the worst of the worst. Hold onto your buddy bracelet before you venture down this wormhole of WTF were they thinking?
Eric (Sean Penn)NBCU Photo Bank
If there was one standout among the six Central Perkians who made the most egregious errors in judgment, it was definitely Phoebe Buffay. And never was she more at her worst than when she decided that yeah, it'd be a swell idea to expose her sister Ursula's romantic fraudulence to her fiancé so that she could swoop in and claim his solar system sweater-sporting self for her own.
Not only was this a lowdown dirty and desperate move, but it also ended up being just as awkward as she deserved it to be when he accidentally hooked up with Urs behind her back. Which was just as well because this was a match made in hell by Phoebe's grandmother.
Elizabeth Stevens (Alexandra Holden)NBCU Photo Bank
Ross' moral compass was often just a tick or two off -- like when he, shudder, tried to cop a feel on his own cousin -- but when he took up with his way-younger student because she admitted to calling him hot on her anonymous eval, it was a new level of head-shake-age.
We're glad she nailed him with that vodka balloon after their break-up. Even his fake funeral was a more scrupulous showing than the way he handled that student crush situation.
Dr. Tim Burke (Michael Vartan)Paul Drinkwater/NBC/NBCU Photo Bank via Getty Images
Monica gave a good speech to her pals about why they had no right to judge her for trying to spark something with Richard's son, but coo coo ca choo Mrs. Robinson, that kiss was twisted beyond.
Richard wasn't somebody she had a brief thing with once upon a time; he was a real-deal relationship, which meant her hooking up with his son was 100% weird.
Malcolm (David Arquette)NBC
Another one of Phoebe's finest moments right here. This time, she accidentally picked up Ursula's stalker ex and somehow wasn't red-flagged straight to retraining order status by the fact that he carried night vision goggles and a creepily detailed diary of her every move.
Ethan (Stan Kirsch)NBC
Not to get too heavy here, but what happened between these two was illegal and immoral. Granted, Monica was duped into thinking her young lover was at consent age when they copulated, but that still doesn't make it OK on any level.
Paolo (Cosimo Fusco)NBC
The "Weenie from Turini" might have had good taste in dress pumps and a swoony accent, but that's about all the good we can say about the guy who felt up Phoebe during the massage appointment Rachel suggested he make. Ross was right to call this dude a crapweasel to his face.
Barry Finkle/Farber (Michael Whitfield)NBC
Rachel braved the rainy City in a tacky wedding dress just to get away from the guy, and yet somehow she found her way back into his arms after he proposed to her former BFF who he'd been cheating on her with before. NO.
Kathy (Paget Brewster)Paul Drinkwater/NBC/NBCU Photo Bank via Getty Images
We were hoping that Chandler's in-the-box thinking time would make him realize that his new thing with Kathy was truly effed up. Not only did she date Joey for a significant (at least, by his standards) period of time, but he actually overheard their bedroom behavior on the reg which makes all his torch-carrying that much creepier.
Oh, and she's no saint either. Not that Joey was some upstanding beacon of monogamy by any stretch, but it was still pretty underhanded of her to hook up with his best friend-slash-roomie -- not nice -- and it was even worse when she got revenge on Chandler for lousily accusing her of something by fulfilling that exact worst nightmare.
Emily Waltham (Helen Baxendale)NBC
There was nothing gross about Ross's relationship with Emily -- OK, that earring proposal thing might've been a little icky -- but that girl was kind of a beeyotch to everyone from the moment we met her.
Sure, Rach should've given her a polite heads up about the change of plans, but what could she really expect from a perfect stranger anyway? The worst part was when she started laying down the law about who Ross could be friends with, where he lived, and what furniture he could and couldn't keep. We were starting to reach psychological abuse status towards the end there.
Susie Moss (Julia Roberts)NBC/Getty Images
Talk about serving up a super cold dish of revenge. It was happenstance which brought Susie Underpants face-to-face with her fourth grade tormentor.
But instead of letting bygones be bygones, she made Chandler's underpants (and the rest of his clothes for that matter) be gone by way of an elaborately convincing seduction ruse because she's petty and mean. And here we thought she hated actors.
Russ (David Schwimmer)NBC
How Rachel managed to find the world's only Ross Geller doppelgänger and not see what was happening, we'll never understand.
Chloe (Angela Featherstone)NBC
Anyone who gets in the middle of lobsters is an automatic addition to the hate list. But The Girl from the Xerox Place, as she had been lustily dubbed by Joey and Chandler, is an especially heinous member because she openly didn't care if she became a homewrecker that night, even if Ross had a marriage on the line at the time.
Parker (Alec Baldwin)NBC
Perhaps the peppiest member of the Friends's dating history, this guy was basically what would happen if a Hallmark card grew legs, got hopped up on sugar, and then hit Disney World during the fireworks show. NEXT.
Erika Ford (Brooke Shields)Brian D. McLaughlin/NBC/NBCU Photo Bank via Getty Images
For a guy who very often had little to offer a potential mate besides "the Joey love" and a few cheesy lines from his Days of Our Lives stint, Joey had pretty good luck finding worth-a-damn dates like Janine (Elle Macpherson) and Erin (Kristen Davis). But he also had the tendency to attract "some stinkers," as he might call 'em, along the way. Like the batshit soap-obsessed Erika, who was so wacked she made Eddie Menuek look stable.