The six friends that frequented Central Perk are some of our favorite characters that last to this day. Rachel (Jennifer Aniston), Phoebe (Lisa Kudrow), Monica (Courteney Cox), Joey (Matt LeBlanc), Chandler (Matthew Perry) and Ross (David Schwimmer) were all so greatly diverse, yet they had a good dynamic. Most of the time.

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While they had plenty of good Friends moments, they were still human beings with flaws. They had their own faults, and sometimes this affected their relationships with one another. So, without further ado, here are 10 of the worst things the friends have done to each other--ranked.

The One Where Monica Bets The Apartment

When she and Rachel are desperate for Joey and Chandler to get rid of the chick and the duck, their knowledge is put to the test in a game of answering deeply personal questions about their friends. This quickly escalates into chaos, and Monica - being competitive as ever - bets hers and Rachel's apartment as added incentive in the game's outcome. Long story short, the girls lost.

While Rachel failed the last question, Monica bet the apartment. Because of this, they were forced to move into the disgusting apartment across the hall. For Rachel, who never wanted Monica to bet the apartment in the first place, this is definitely one of the worst things Monica has ever done to her.

The One With The Fake Girlfriend

In Season 1, Joey has Monica pose as his date in order to get to a girl he used to date. Unfortunately for him, she's with someone else. Telling Monica that the guy his ex-girlfriend is currently with is meant for her (and that he is said ex-girlfriend's brother instead of date), the two set off for a calamitous date night.

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Poor Monica is confused and disgusted when Joey's ex-girlfriend and her supposed brother act more flirty and inappropriate than brothers and sisters should, to which Joey finds himself caught in the lie and confesses to using her. The two then conspire to break up the happy couple, and keep what's left for themselves.

The One Where The Sandwich Trumps Human Lives

While on a ride-along with a cop boyfriend of Phoebe's, the guys, all sitting in the backseat of the cruiser, mistake a car's backfire for a gunshot. Joey dives over Ross, as though to protect him, and Chandler is stung that Joey would choose Ross over him in a dangerous situation.

While the episode depicts this incident as a hilarious moment in that Joey was really going for his sandwich, it's also one of the worst things Joey's ever done. He could always get another sandwich. He can't get a new Ross or Chandler. Hopefully, Joey would ditch the sandwich for his friends next time.

The One With The Untimely Death

When Chandler and Ross's alma mater creates a website to post and catch up, the two engage in a battle of wills about what they've been up to since graduation. The battle spirals into Ross writing a "coming out" post for Chandler, who receives plenty of congratulatory calls from people they went to school with. In retaliation, Chandler posts that Ross was killed by a blimp.

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Really, this battle shows some of the nasty things Chandler and Ross did to one another, but this was particularly cruel on Chandler's part - especially when so few people showed up to Ross's fake memorial service. Tragic.

The One With The Secret Keeper

Chandler and Monica tell Joey that he has a room at their new house in the suburbs in Friends

When Chandler and Monica first got together, they wanted to keep it to themselves. Understandable, considering they'd been friends for so long and wanted to see where it went before anything became official. Unfortunately, Joey was tasked with keeping the secret.

Now, this was a difficult spot for Chandler and Monica to put Joey in, as he doesn't like secrets and he tells their group pretty much everything. He even had to pretend to be a pervert at one point in order to keep up the charade. Monica and Chandler tried to make up for it but mostly, Joey was on his own. The stress of keeping their secret was too much on Joey's conscience, especially when he was pressured by the others to tell them everything.

The One Where Rachel Breaks Joey's Heart

Shortly after Ross and Rachel sleep together and she becomes pregnant, Joey develops feelings for her. He gathers up enough confidence to confess to her, and she unfortunately reacts badly. At first thinking it was a joke, then sadly telling Joey she didn't return his feelings, it ultimately broke Joey's heart and made things awkward between them. Rachel had to lie to him about her boss buying her baby just so they could talk again.

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What makes this incident especially cruel, however, was that Rachel developed feelings for Joey after having already turned him down. Rachel has a hard time making up her mind, but in this instance, she toyed with Joey's feelings a little too loosely.

The One Where Phoebe Mugged Ross

Lisa Kudrow as Phoebe, Jennifer Aniston as Rachel. Matt LeBlanc as Joey, and David Schwimmer as Ross in Friends – backup

Phoebe's got a checkered past. She had an unusual and tragic family situation, she lived on the streets, and honestly, we've only heard bits and pieces of it. However, we know something big: she mugged Ross when they were kids. She claims it's cool that they have a connection that goes way back, but Ross is (understandably) not so pleased, especially since he was traumatized by the incident.

Luckily, Phoebe kept a box of things from her time on the street, one of which was a science comic Ross made. They share a heartfelt moment in which Phoebe tells Ross his comic taught her a lot, which seems to be the turning point. Really, it's not the best history, and Phoebe tried to make up for it; however, it's without a doubt the worst thing she ever did to him.

The One Where Rachel Was A Wedding Crasher

Friends Season 4 Episode 24 Rachel Ross Wedding

Rachel initially decides not to go to Ross's wedding as she is distraught at the idea. Then, in a whirlwind and with Phoebe trying to stop her, Rachel rushes to London and tell Ross how she feels before he marries Emily. Obviously, Rachel has the worst timing in the world. And to be honest, in Rachel's state, her judgment was clouded and she shouldn't have been making any decisions, especially last-minute ones the way she did.

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Actually, her presence at his wedding likely caused Ross to say the wrong name at the altar, and we all saw his marriage spiral downhill from there. This was definitely one of the most selfish acts Rachel ever committed.

The One Where Chandler Can't Stop Kissing Girls

Chandler and Joey are best friends. They've operate on the same wavelength and been through so much like Joey licking the spoon and putting it back in the drawer, Joey moving out, and Chandler kissing Joey's girlfriend Kathy and then one of Joey's sisters... and not remembering which one.

The worst thing Chandler ever did was kiss Joey's girlfriend behind his back, and then kiss one of his sisters in a drunken stupor and not remember which one. Honestly, both were highly disrespectful and echoed betrayal. Yet, Chandler more than made up for it and the two have remained best friends.

The One Where Ross Was Literally The Worst Boyfriend Ever

Jenifer Aniston as Rachel and David Schwimmer as Ross in Friends

Ross did some pretty underhanded things to Rachel. In fact, we have a list of his nastiest hits: cheating on her when they were "on a break," doing everything to cover it up and lie about it, marrying her and then not telling her he never got an annulment, and then holding her back from an amazing job and new life in Paris in the series finale.

Their relationship was all kinds of dysfunctional, even if Ross thought he was doing these things for the right reasons or out of good intentions. Still, these incidents tend to overshadow the good that Ross has done for Rachel, and things aren't looking good for him in the "best boyfriend ever" department.

NEXT: Friends: 5 Times Ross Was A Good Guy (& 5 Times He Was A "Good Guy")