Friends: The Most Awkward and Cringeworthy Romances

Friends still reigns supreme on streaming services worldwide because it captures audiences’ love with charismatic characters, witty one-liners, and romantic pairings straight out of a scripted version of The Bachelor. Romance emanates through Central Perk, Monica’s (Courteney Cox) apartment, and 1990s New York City with plenty of gusto. Why wouldn’t it? These six pals are attractive, likable, and ready to mingle!

We adore pairings like Ross (David Schwimmer) and Rachel (Jennifer Aniston), Monica and Chandler (Matthew Perry), and Phoebe (Lisa Kudrow) and Mike (Paul Rudd). They fit together like cranberry and turkey on Ross’s stolen leftover sandwich on Thanksgiving. But what about the couples that didn’t work out? Not only do they feel like two jigsaw puzzle pieces that don’t fit, but these romantic couplings were downright weird to watch! These are the most awkward relationships on Friends.

Rachel and Joey

Plenty of romances took place within the friend circle of the show’s main characters, but the one starting in season 8 between Rachel and Joey didn’t sit right with many folks. The arc took place during another one of Ross and Rachel’s sabbaticals, and fans at home were longing for the show’s ultimate on-and-off couple to finally settle down as the show came to a close. Seeing Rachel and Joey experiment with something more than a platonic friendship threw a wrench in those plans momentarily, resulting in some unhappy viewers. Hindsight says that Rachel and Joey’s chaotic chemistry may have been a better match than many gave it credit for, though. 

Monica and Timothy

Monica and Richard (Tom Selleck) were one of the better couples in the show. Monica and Richard’s son, Timothy (Michael Vartan)? No thanks. Both people let superficial physical attraction lead to an uncomfortable balcony kiss one Thanksgiving night in season 4. Timothy reminds Monica of Richard, and Monica reminds Timothy of his own mother! Even though the whole thing is weird, it added to the tradition of turkey day madness in the series. 

Alice and Frank Jr. 

Phoebe’s younger brother, Frank (Giovanni Ribisi) has a steady relationship with a much older woman, Alice (Debra Jo Rupp), starting in season 3. The power dynamics and age gap between them make for some eerie and awkward humor, but the two mismatched lovebirds adore each other all the same. Phoebe eventually serves as a surrogate for her baby brother and his wife in season 5. 

Ross and His Cousin

This isn’t Game of Thrones we’re talking about here. The friends of Friends don’t want any incest-adjacent feelings in their hearts . . . except for Ross in season 7. In one of the show’s most difficult scenes to rewatch, Ross tries to kiss his cousin (Denise Richards) while David Schwimmer delivers a hilarious and uncomfortable inner monologue in the aftermath of his taboo urge. “The One With Ross and Monica’s Cousin” gives “Scott’s Tots” from The Office a run for its money in cringe worthiness. 

Chandler and Joanna 

Seeing Chandler with anyone but Monica feels wrong. The time when he decides to date Rachel’s boss, Joanna (Alison La Placa), in season 4 has to take the cake as the worst decision Chandler makes in his non-Monica love life. Joanna gets a little too kinky by handcuffing Chandler to an office chair and Rachel tries to help her buddy get out. Other than the obvious awkwardness of the show oversimplifying the dangers of nonconsensual sex, Chandler and Joanna felt like something out of a cheap porno on the deepest reaches of the dark web.  

Rachel and Russ

The Ross and Rachel romance came storming out of the gate as toxic as ever in the first two seasons of the series. After one of their initial breakups, Rachel starts dating a Ross doppelganger (also played by David Schwimmer) and stays blind to her infatuation with the nerdy paleontologist. There’s a palpable awkwardness to the scene that is only cut into by the show’s reliance on one of the 1990s’ ultimate sitcom trends: showing the same actor on screen at the same time playing two different characters. This almost never works out well on TV (except for the brilliant work done by Erin Moriarty in The Boys season 4.)

Phoebe and Parker

We should all view the world like a glass half full of milk, even when life gets tough. Oftentimes positivity can be nauseating because, let’s face it, the world just isn’t that great. Phoebe initially finds Parker (Alec Baldwin) to be an upbeat mate. His big smile and optimistic demeanor get the best of the gang pretty quickly, though. The storyline allows Baldwin to shine as he always does in sitcoms. 

Joey and Ursula

Of all of the characters on Friends, Joey probably has the least amount of romantic luck. Sure, he shares his bedroom with a new woman every night, but the show’s resident himbo doesn’t know the first thing about serious relationships. One of his most uncomfortable decisions was going out with Phoebe’s evil twin sister, Ursula. Lisa Kudrow does a fantastic job playing both her usual role and this new one in season 1. 

Ross and Janice

Other than her trademarked nasal being about four octaves too high for human ear consumption, Janice (Maggie Wheeler) is a demanding, overbearing, and incompatible mate for Chandler before he marries Monica. Things get really weird when Ross gives his friend’s ex-girlfriend a try in season 5. For being a scientist, Ross surely doesn’t understand the first thing about chemistry. OH. MY. GOD! 

All seasons of Friends are available to stream on Max in the U.S. and Netflix in the U.K.