Oh, Ross. He was such a mess a majority of the time on Friends. He provided some pure comedic gold for sure, but he was also kind of despicable a lot of the time if you look at his actions outside of the comedy of the show. Ross was always uptight with a fair amount of quirks.

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Most of Ross’s screen time was spent digging himself in deeper holes until it would all implode in his face. For someone who started out on the show looking bewildered and lost half the time he still had a constant rotation of ladies in his life. Many who make this list below as collateral damage of the most shameless things Ross ever did on Friends.

The One Where Ross Doesn’t Get An Annulment

Rachel and Ross with marker on their faces in Friends.

Back at the end of season 5, Ross and Rachel get drunk in Vegas and wind up married. “Hello, Mr. Rachel.” Cute. Funny. Perfect season 5 cliffhanger. Cut to season 6 and we find out that Ross hasn’t exactly gotten the annulment like he told Rachel he would. He doesn’t want to be the guy who’s been divorced 3 times. So obviously he keeps it a secret and doesn’t let Rachel know they’re still married. We all know that wasn’t going to remain a secret for long and Ross is eventually outed, and they get a divorce.

The One Where Ross Dumps Bonnie

Ross and Bonnie on the couch

I don’t know if anyone has ever accused Ross of being deep, but when Ross dumps Bonnie because she shaves her head his shallowness is really showing. However, this little act might show just how perfect Rachel and Ross are for each other. Because Rachel is the one who convinces Bonnie she should shave her head, knowing that Ross won’t be able to handle it.

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Bonnie gets caught in the crossfire of the lingering feelings between Ross and Rachel.

The One Where Ross Dates A Student

Season 6 really cranks up the ick-factor when Ross starts dating one of his students. Sigh. There’s so much wrong with this. First of all, no. Don’t date a student. Even if the age gap isn’t that large in reality, it’s just wrong. He knows, we all know it. They have to keep their relationship a secret because, you know, it’s unethical for a professor to date his student and Elizabeth doesn’t want her overprotective dad finding out. Ultimately the age difference catches up to them and they break up, but not before Ross goes on spring break and acts a fool, just so he can make sure Elizabeth doesn’t cheat on him. Not your finest hour, Mr. Geller.

The One With The Videotape

I’m going to give Ross a little leeway on this one, although it’s still shameless. In season 8, the gang wants to find out how Rachel got pregnant. The episode is masterful, connecting the b-story back to the a-story. Joey’s talking about the fake names he gives the women he sleeps with (keepin' it classy Joey) and shares the “magic” story that can get any woman in bed. In the meantime, we find out there’s a videotape of Ross and Rachel making babies (or baby), that Rachel has no clue exists. The story all comes out and it’s somewhat justifiable, but still, really Ross?

The One Where Ben Can’t Play With A Doll

Ross handing G.I. Joe to Ben

There are some early episodes of Friends that don’t necessarily wear well over time. This one pops up in the third season and shows a side of Ross that’s not very appealing. Ross has his son Ben with him for the weekend and isn’t pleased when Carol drops Ben off holding a Barbie Doll.

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Ross spends the rest of the episode trying to swap out Ben’s Barbie for more manly toys, like GI Joe or dinosaurs. Just let the kid play with whatever toy he wants, dude. What exactly is Ross afraid of? That playing with dolls will make Ben gay (insert eye roll)? You know, like his mom? Not the most flattering representation of Ross.

The One With The List

Word of advice. Never make a pro/con list about a person you’re thinking of dating. Unless it’s a mental list. If Friends has taught us anything it’s that this can never end well. In season 2, just as Rachel’s figured out she likes Ross and Ross finds out Rachel likes him, and we think they might get together… pump the breaks. Ross is dating Julie and Joey and Chandler suggest Ross make a list to help him decide who to date. Ross, why would you ever take advice from those two? Especially lady advice. The list is super insulting and of course, Rachel finds it. Roadblock to Ross and Rachel, back in place.

The One Where Ross Doesn’t Break Up With Mona

Let’s head back to season 8 because Ross is on a real roll this season. He knows Rachel’s pregnant (remember he has the video to remind him) and he’s been dating Mona since they met at Monica and Chandler’s wedding. Here’s the thing, he doesn’t tell Mona that Rachel’s pregnant. Mainly it’s because he’s a big chicken who doesn’t like to face problems of his own making. Now, a little bit in Ross’s defense here, Mona was kind of in a hurry to lock things down. She was getting personalized Christmas cards made for them to send out to their friends (too soon Mona), and things spiral from there. Ending with Ross giving Mona a key to his place only to change the locks. Just cut the cord buddy. As Ross says in the episode, "In a way, I judge her for not breaking up with me sooner." You and me both.

The One Where Ross Is All Jealous And Clingy

Rachel at work surrounded by Ross cards

Ross flips-flops over the seasons as someone who is supremely confident and pitifully insecure. Nothing demonstrates this more than Ross’s jealousy and distrust over Rachel’s coworker Mark, in season 3. Ross starts overt proclamations of his relationship with Rachel in the form of flowers, teddy bears, candy delivered to Rachel’s new job, and ends with him essentially saying that Rachel got her job because Mark wants to sleep with her. Nice. Super supportive. Rachel finally has the job of her dreams and Ross is jealous because she has to go to work. It’s not a good look for Ross.

The One With The I Hate Rachel Green Club

Okay, let’s be honest, this one is probably as funny as it is shameless. Back in high school, Ross was epically in love with Rachel who ignored him. He was a nerd, she was popular, got it. We find out in season 8 that Ross started up the I hate Rachel Green club with one of his friends that Rachel hadn’t been so nice to (hello guest star Brad Pitt). There was also a foreign exchange student in the club, but he didn’t know why he was there. Ross was trying to mask his feelings, pretending he hated Rachel so no one would find out how much he really liked her. This one might get a pass because Rachel earned it with her own behavior.

The One When Ross Said The Wrong Name

Ross and Emily walking down the aisle in Friends

Ross might be a hopeless romantic. He’s constantly searching for love and digs his claws in once he gets a target in sight. Ross and Emily have a whirlwind (re: way too fast, you should have slowed down) romance and he proposes after they’ve only known each other a brief 6 weeks. Before you can blink the gang is in London, sans a pregnant Phoebe and Rachel. Rachel changes her mind and pops up at the church as Ross and Emily are doing their rehearsal. With Rachel’s surprise appearance on the brain, Ross mucks up the ceremony and says Rachel’s name, instead of the woman he’s marrying. They still go through with the marriage, although it doesn’t last. Bad form, Ross.

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