On Friends, six gorgeous single people in their ’20s and 10 seasons add up to a whole lot of relationship drama. Fans can relate to Ross, Rachel, Phoebe, Monica, Chandler and Rachel because they all encounter a wide array of speedbumps on their respective journeys to find love.

Every member of the gang does some pretty shady stuff as they search for their soulmates including giving out fake names, dating multiple people at the same time, forgetting to mention impregnating an ex, some minor stalking, getting drunk and disorderly and a wide assortment of other bad behaviors. Here are the 10 worst things the gang did to a romantic partner.

Ross Cheats On Rachel

Ross and Rachel remain one of TV’s best couples, but their relationship was far from perfect. After finally getting together during season 2, Ross’ jealousy coupled with his less than supportive attitude regarding Rachel’s career leads to a fight that ends in a “break” (the exact meaning of this remains a contentious topic between the two for the remainder of the series) during season 3. Ross immediately hooks up with the hot girl from the copy place.

It’s a toss-up if Ross’ worse move is having sex with someone just a few hours after he and Rachel’s relationship hits a bump or the extent he goes to keep her from finding out instead of confessing. So while Rachel spends the night leaving Ross messages about making up, Ross spends it fornicating with a girl with a tramp stamp.

Ross Says The Wrong Name During His Wedding

Ross and Rachel appear destined to be together until Ross falls for Emily Waltham during season 4. Ross, tired of trying to woo his lady love from across the pond, decides to propose after just a few months of dating. Everybody’s on board with this ship except for Rachel who realizes she’s still in love with Ross and needs to tell him how she feels. But at the last moment, Rachel decides letting Ross go is the best wedding gift she can give.

It seems Ross is going to get his happily ever after until he calls Emily “Rachel” during his vows. Hey, there is never a good time to blurt out an ex’s name, but doing it while marrying someone else makes the top of the no-no list. Ross looks as shocked as Emily, and his love for her seems genuine, but it’s hard not to view this as some kind of self-sabotage. Accident or no accident, Ross humiliates Emily, and their marriage is on the rocks once they say “I do.”

Chandler Dumps Janice On New Year’s Eve

Before settling down with Monica, Chandler struggles to find Ms. Right. The closest thing he has to a girlfriend during the first few seasons is his on-again-off-again relationship with the uber-obnoxious Janice whose nasally voice is as equally annoying as her braying-cackle hybrid of a laugh.

Chandler rekindles their romance just so he can have someone to kiss at midnight on New Year’s Eve. Janice’s grating personality causes Chandler to dump her before the clock strikes midnight. Breaking Janice’s heart on a holiday that comes in second only to Valentine’s Day as the most romantic day of the year is just cold-hearted.

Rachel Leaves Her Groom At The Altar

On the first-ever episode of Friends, Rachel, a spoiled daddy’s girl with a Mrs. degree and no marketable skills, Rachel runs out on her wedding to Dr. Barry Farber. Faced with a lifetime of being a lady who lunches and lamenting her lackluster sex life, Rachel crawls out a bathroom window, leaving her groom waiting at the altar.

If Rachel was going to have second thoughts, it should have been about the horrendous wedding dress she chooses for her big day. The runaway bride does try to make amends with the jilted groom … via his answering machine but is more concerned about being cut off financially by her father. Karma eventually catches up with Rachel, and it takes her until the season 2 finale to put her nixed nuptials behind her.

Chandler Gives Monica A Reused Mixtape

When Both Chandler and Monica forget to get each other gifts on Valentine’s Day during season 6, Chandler frantically searches for some token of his affection. He finds an old mixtape, and because he’s short on time, he hands it over without listening to it first. Monica is so touched by the thoughtful gift, she goes out of her way to make up for her thoughtlessness.

Chandler capitalizes on Monica’s guilt to get gifts, yummy treats and sexual favors. Chandler gets busted over macaroni and cheese with cut-up hot dogs when he and Monica discover Janice made the tape for Chandler years earlier. On the scale of total dirtbag to grade-A jerk, Chandler falls somewhere in between.

Phoebe Spoils Mike’s Proposals

Mike’s a bit gun shy when it comes to marriage, but his devotion to Phoebe overrides his fears. Mike runs into some unexpected troubles when the time comes to propose as Phoebe inadvertently thwarts Mike’s attempts at a memorable proposal.

The more Phoebe tries to rectify the situation and give Mike the confidence to pop the question, the worse things get. Phoebe isn’t trying to smash Mike’s ego to bits and insult his idea of a grand romantic gesture, but the result is the same if she was doing it on purpose.

Joey Asks Rachel To Break Up With Someone

Joey is the undisputed womanizer of the group, but his hijinks are of the love ’em and leave ’em variety. Joey may not be the brightest guy, but he’s smart enough to get Rachel to break things off with a girl for him. It turns out Joey’s been getting Chandler to do his dirty work for years. This involves Chandler giving the “It’s not you, it’s Joey” conversation over pancakes. Letting women down easily isn’t Rachel’s thing, so she decides to play matchmaker instead. But in the end, Erin’s just not that into him, and Joey becomes the dumpee instead of the dumper.

Phoebe Dumps David

Following Phoebe’s break up with Mike Hannigan during season 9, she rekindles her romance with physicist David. The only problem is Phoebe’s still carrying a torch for Mike but doesn’t see a future with a man who has taken the possibility of marriage off the table.

The whole gang heads to Barbados where David plans to propose to Phoebe. Mike shows up just as David’s about to pop the question and beats him to the punch. Phoebe turns Mike down, but the two declare their love for each other, and David has to witness the whole thing. A rebound fling is one thing, but jumping into another relationship with a former flame is a bad call on Phoebe’s part, especially when the aforementioned former flame has been living like a monk is Russia and is still crazy about her.

Monica Lies About London

As Monica and Chandler’s wedding day draws closer during season 7, a shocking revelation causes some serious awkwardness between Chandler, Monica and Joey. Chandler finds out he wasn’t Monica’s first choice. A depressed, drunken Monica goes looking for a no-strings-attached one night stand with … Joey. Monica never bothers to tell Chandler (Phoebe spills the beans) because she didn’t think it’s important (yeah, right). Chandler feels like a consolation prize, and there’s no doubt Monica should have come clean sooner.

Monica Has Lunch With Her Ex

Monica and Richard break up at the end of season 2, but it’s no secret she carries a torch for him for years. That’s why Monica is hesitant to tell current boyfriend Chandler after she bumps into her ex, and they have lunch together. She does confide in Phoebe about the run-in but makes it clear Richard is now in the friend zone.

Monica obviously feels a bit guilty about keeping the secret and uses the excuse that Chandler will freak out, and it will ruin their first anniversary as a couple. But by not telling Chandler, she breaches his trust and gives him a reason to doubt she’s really over Richard. Monica’s biggest mistake is telling Phoebe because nobody in this group can keep a secret.