Popular sitcom Friends started out with the central relationship of the show being the will-they-wont-they dynamic between Ross and Rachel. The relationship between Monica and Chandler that developed after a one-night-stand in London was never meant to be anything more than a brief storyline before things returned to their status quo.
However, audiences immediately signaled they had fallen in love with the pairing, and Monica and Chandler became the new standard for a loving, supportive relationship on the show that culminated in a happy marriage and twin babies. But things were not always hunky-dory between the two during the decade of the show's runtime, as evidenced by these 10 instances.
10 Monica: Rejected Chandler Repeatedly
Back before the two became an item, Chandler had always made his admiration for Monica clear, calling her the most beautiful woman he had ever met and one of his favorite people. Monica's feelings, on the other hand, were a little less intense. She treated Chandler like a good friend, but when he asked her if she would ever date him, she laughed in his face.
This clearly puzzled Chandler and hurt his ego, and he spent an entire episode while they were at the beach house repeatedly asking Monica what it was about him that made the idea of dating him so laughable to her. He never really got a straight answer.
9 Chandler: Called Monica Fat
The first time Chandler and Monica met was when Ross brought him home for thanksgiving. At that time she was in high school and he was a college stud. At least, as much of a stud as Chandler is capable of being. Monica immediately developed a crush on him and followed him around all night. Chandler was less enthused, and Monica heard him calling her 'fat' to Ross, to her complete mortification.
So deep were her feelings of humiliation and distress that they motivated her to go on an extreme diet and exercise regime that melted the accumulated fat of a lifetime off of her in a year.
8 Monica: Cut Off Chandler's Toe
Back before they were the greatest of chums, Chandler was simply a guy that Monica greatly disliked for dissing her weight. One thanksgiving, Ross invited Chandler over to his house, where Monica planned to humiliate Chandler by first pretending she wanted to get with him and then revealing it was a ploy and laughing in his face.
The plan did not go according to its design, and Monica instead ended up tossing a kitchen knife straight at Chandler's shoe, catching him at the tip of his toe. While Chandler was taken immediately to the ER, any chance of retaining the limb was lost when Monica brought along a frozen piece of carrot instead of his missing toe.
7 Chandler: Crushed Monica's Spirit
During the early days of their friendship, Monica was out of a job and cottoned onto the task of helping Chandler lose weight as a way to pass the time, a process that Chandler was definitely not a fan of.
After trying every which way to refuse to exercise with her, to no avail, he finally decided to remind Monica of everything that had gone wrong in her life up to that point, to crush her spirit so effectively that she would lose her optimistic attitude, and only want to curl up in her bed and sleep. The ruse was depressingly effective.
6 Monica: Revealed Chandler's Darkest Secret
Right from the start, even before they started dating, Monica and Chandler were closer than the other friends. So much so that they knew quite a few of each other's deepest secrets. When Chandler once accidentally revealed one of Monica's secrets, she retaliated by revealing that Chandler has a third nipple.
This then became a recurring joke on the show, with the others constantly ribbing Chandler about his condition until he had finally had enough and had the skin abnormality removed via operation.
5 Chandler: Took Monica's Apartment
One time Chandler and Joey challenged Rachel and Monica to a game over who knew the other better. The boys won, and as part of the bet, Monica and Rachel had to give up their apartment in exchange for Joey and Chandler's considerably less nice one. It was a bitter pill to swallow, and Monica had to spend several episodes trying to adjust to her new apartment.
Things finally came to a head when Monica and Rachel found the conditions in their new apartment too much to handle and managed to trick the guys into switching apartments again.
4 Monica: Choose A Job Over Being With Chandler
When Chandler was accidentally transferred to Tulsa by his company, Monica ordered him to get the decision revoked. Despite trying his best, Chandler did ultimately move to Tulsa and Monica prepared to go with him. But then she got a job offer from a high-end restaurant to be the head chef.
Monica then decided to stay back in New York without Chandler and felt guilty about having to break the news to him. Naturally, Chandler felt hurt at being left on his own in Tulsa, but he still supported Monica's decision and ending up missing her so much while in another state that he decided to quit his job.
3 Chandler: Pretended He Didn't Want To Marry Her
When Chandler was gearing up to ask Monica to marry him, he hit upon the bright idea to surprise her by first pretending he has no interest in ever getting married. The plan worked too well, and Monica was deeply upset to find out that her boyfriend had no intention of taking the next step in their relationship.
So agitated did she become that she was preparing to leave Chandler and go back to her ex Richard until Joey caught up to her and finally explained Chandler's misguided ruse.
2 Monica: Confessed She Had Wanted Joey
In the lead up to the wedding, Monica and Chandler were writing their vows and during the process, it was revealed by Phoebe that it was not Chandler that Monica had plans of hooking up with back in London. After being pressed by Chandler, Monica revealed she had come to his room that night hoping to have a one-night-stand with Joey. This caused Chandler to begin to spiral.
He had always been conscious of how much more attractive to women Joey was than him, and to realize that the love of his life also shared that preference was like a punch to his gut, stoking his insecurities and causing a rift between Joey and Chandler.
1 Chandler: Ran Away From The Wedding
When Monica and Chandler were about to get married, Chandler developed cold feet and ran away from his apartment. This set the other friends on a frantic scavenger hunt before Monica could find out. They did manage to find Chandler and convince him to return to the wedding, but Monica eventually found out the love of her life had considered leaving her at the altar.
It made Monica doubt her relationship with Chandler, and she even added 'But only if you want to' to her wedding vows after saying she wanted to spend her life with him.