Friends: 8 Hilarious Reasons Why Chandler Broke Up With His Girlfriends – Screen Rant

Chandler’s break-up reasons are as hilarious as his one-liners. A dramatic revenge scheme and gross mascara goop all play their part, as seen below.
Chandler Bing from Friends dated quite a few women before falling head over heels for Monica Geller. He was with women who came from diverse walks of life, such as a philosophy major, a fashion executive, and a theatre actor.
RELATED: 10 Biggest Ways Friends’ Chandler Changed From Season 1 To The Finale
While Chandler’s girlfriends brought something impressive to the table, they barely stuck around. The reasons being his picky dating mannerisms, past mistakes, and lack of trust. He’d find dumb reasons to make the relationship harder for himself and his partner. Every affair mentioned below is proof that Chandler was a bad dater. He’d either lose interest, nitpick, or fail to curb his jealousy.
Chandler dated the fashion executive, and Rachel’s superior, Joanna twice in seasons 3 and 4. He met her one fine afternoon in “The One With the Dollhouse” at Bloomingdale’s and she expressed an immediate interest in him. They went for a dinner date at the end of which Chandler left her hanging.
Joanna and Chandler seemed to get along well until it was revealed that the irritant in their relationship was the mascara goop formation at the corner of her eye. Eventually, Chandler told Joanna about the mascara goop but it’s utterly hilarious how a man of his caliber couldn’t work past it.
Marjorie was a one-off character who dated Chandler in “The One With All The Wedding Dresses”. They met when Chandler accompanied Joey to a sleep clinic. He asked Marjorie what she was in for and she replied she talked in her sleep. They had a pleasant conversation and she agreed to go out with him.
Turns out, Marjorie did a little more than talk in her sleep, which for Chandler was a dealbreaker. Her sleep-screaming scared the bejesus out of Chandler. Now, he should have stuck around given the fact that she was seeking treatment for her disruptive sleep disorder. But the Chan-Chan man scares easy and she was never to be heard of again.
Susie Moss’ antics caused the breakup in “The One After the Super Bowl, Part 2” when Chandler found himself in a sticky situation. Susie bumped into him while he was touring the sets of Outbreak 2: The Virus Takes Manhattan. She worked as a hair and makeup artist and he was there to see Marcel with Ross and the gang. They had a bit of history, and certainly not a pleasant one.
RELATED: 5 Of Chandler’s Girlfriends From Friends We’d Love To Date (& 5 We Wouldn’t)
Chandler had lifted Susie’s skirt during a school play and the rest of the kids her given her a hard time for years. She’d since then nursed a grudge against him, and now, sensed the opportunity for revenge. Long story short, Susie had made Chandler wear women’s underwear on their dinner date, and made him strip all his clothes in a bathroom stall. Before leaving with his clothes, she told him about the repercussions of his childhood mischief. Chandler had a rather creative way to tell her they were over, “I hope you realize you’re not getting these underpants back!” he’d shouted as she shut the toilet door on him.
Chandler was enamored with Kathy, and this time, his mistrust stood in the way. This was a once-in-a-lifetime love and he had done everything in his power to indirectly say he loved her. Only, she was his best friend and roommate, Joey’s girlfriend, and he didn’t want to hurt him.
Chandler bought Kathy a rare copy of her favorite book The Velveteen Rabbit for her birthday, and almost risked his friendship with Joey in the process. But once they got together, the relationship didn’t last long after Chandler went to one of her plays. He accused her of cheating because the script demanded her character be sexually assertive on stage. This accusation was based on Joey’s theory that actors who shared on-stage chemistry lacked it in real life. This laughable theory cost Chandler his relationship with the woman he was meant to be with.
Believe it or not, someone as mistrustful as Chandler tried his best to be with a polyamorous Italian woman named Aurora. Obviously, his jealousy got in the way and their wonderful romance came to a screeching halt.
On their first date, she’d told her about her adventures in Yemen with her husband Rick. The thing is Aurora had been an open book and each time they met, she’d mentioned another romantic interest. Eventually, Chandler’s resentment got the best of him and he was torn between the two voices in his head. The first guy reminded him what he had with Aurora was great and the second guy welled up every time she left. Chandler listened to the second guy and kissed Aurora a final goodbye saying, “Sorry, the first guy runs the lips.” She laughed and so did the fans.
Ah, Danielle, the perfectly good woman who came down to Central Perk in search of Chandler only to be fobbed off. Chandler described their first date as the greatest of all time but decided to dangle her because he didn’t want to look pathetic. He played all kinds of games to come across as cool, all of which only proved he was the absolute worst at flirting. And when he did leave a message, he pretended he was in a restaurant by rattling spoons in a dish.
RELATED: Chandler’s Girlfriends In Friends, Ranked
A couple of things prevented the two from talking over the phone, starting with Chandler switching off his phone, to Danielle having his number wrong the whole time. Finally, when Danielle came down to see if Chandler was okay, he backed out saying she was a needy person. It’s hilarious how he projected his insecurities on her, when in fact she came across as a confident woman to fans the whole time.
There’s no denying that Chandler and his friends treated his recurring girlfriend, Janice, horribly. Chandler changed his mind about Janice often – sometimes he’d dump her twice in several months, and at other times, he’d physically stop her from leaving him.
This particular time in season 4’s “The One With All the Rugby,” Chandler bumped into Janice at a nail salon. She was no longer married, he was single, and nothing could have stopped them from being together if Chandler’s picky behavior hadn’t come in the way. Apparently, Janice’s laugh, voice, and personality were strong reasons to call off the relationship. Chandler couldn’t be straight with Janice, so he pretended to move to Yemen indefinitely until his company found an energy source to replace fuel. She definitely did deserve a lot better than a person who was always unsure of her.
Chandler’s mishandled affair with his junior, Nina Bookbinder, makes him one of the worst bosses on Friends. In “The One With Two Parts, Part 1,” his companys’ Annual Net Usage Statistics (ANUS) report was in and the numbers were terrible. Chandler was supposed to fire Nina on Mr. Douglas’ orders but asked her out instead. And so, unaware she didn’t have a job, she showed up at work every day.
Chandler spun all kinds of stories about Nina to his co-workers. But when he knew he couldn’t risk it anymore, he ended up telling her everything. Things seemed to be going well between them initially, but the ANUS report came in their way.
NEXT: Every Worst Date Friends’ Chandler Had, Ranked
Rei strongly believes pop culture shapes human lives. Sitcoms, dramas, and movies have helped her survive the impact of the geopolitical conflict of her homeland. Rei is particularly concerned about the media portrayals of gender, class, race, and sexuality on television and ultimately about how people perceive these things. Every piece she authors is essentially analyzed through a feminist lens. You may find her at: [email protected]

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