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At the end of season 4 Monica began an affair with her close friend Chandler. This happened at Ross's disastrous wedding to Emily in London. Monica was upset after a guest mistook her for Ross's mother and turned to Chandler for comfort none of this is learned until season 5 though. They kept their relationship secret for a while but eventually Joey found out. The rest of the group then found out one by one, until everybody knew. The two fell in love and eventually moved in together, forcing Rachel to move out.
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After living together for a year, Chandler decides he's ready to propose to Monica, purchasing a ring with Phoebe's help, and he takes her out to her favorite restaurant for a romantic evening. However, the evening doesn't go as planned; Richard shows up and is seated at the next table.
When they get home, still not engaged, but first Phoebe and then Rachel asks to see Monica's hand, Chandler is upset believing his surprise has been ruined.
Phoebe and Joey convince him it's not, that all he needs to do is take a couple of days convincing her that he's nowhere near ready to get married, then it will still be a surprise when he actually does propose. His plan goes off a little too well, and things get even more out of hand when Richard shows up and tells Monica he still loves her and wants to marry her. Monica is very upset about how unfair it is, saying that "fair" would have been if Richard had wanted to marry her back when she was still in love with him, or if Chandler wanted to marry her now.
Meanwhile, Chandler frantically searches for her, worried that he's gone too far in pretending he didn't want to get married and that he might have ruined everything. When he returns to their apartment that evening Joey had already explained everything to Monica, and she was there waiting for Chandler with hundreds of lit candles all over the room.
Monica gets down on one knee and tries to propose, but she starts crying so much she can't finish it, so Chandler gets down on one knee as well, telling her that she makes him happier than he ever imagined he could be.
Telling Monica that he will spend the rest of their lives trying to make her feel that happy, he asks Monica to marry him, and Monica says 'yes'. In Season 7the two planned how their wedding was supposed to be but unfortunately, her parents already spent her money for buying the beach house.
But Monica wants the perfect wedding so Chandler eventually decides he will spend all the money they have but Monica decides that she wants a marriage and not just a big wedding. Luckily, Jack understands how embarrassed Chandler feels and agrees not to repeat it.
Monica & Chandler - The One
Monica's mom decided to get their wedding announced in the newspaper but Chandler was unphotogenic that he can't take a good picture with Monica " The One With The Engagement Picture ". Joey decided that he would officiate their wedding and gets his minister certificate on the internet.
Monica tells the story of how they got together. Chandler finds out that Monica wanted to sleep with Joey when she knocked on the door but Chandler was the only one there. Chandler is really upset and doesn't want Joey to do the wedding anymore. Joey talks to him about how Chandler and Monica are meant for each other and nothing could take that away and Chandler is happy to let Joey officiate the wedding. With a month left before the wedding, Chandler and Monica faced the issue of their wedding vows.
With each person coping with their own problems in writing the vows, they turn to memories of past events to help them, showing classic scenes from the first 6 seasons between Monica and Chandler. In the end, the only real problem is who will be saying the vows first. With Two weeks left before the wedding, Chandler reveals that he didn't invite his own father. Monica claims that he would regret not having his father at his own wedding and also that she wants to get to know her future father-in-law.
Chandler protests, telling her that his father embarrassed him a lot as a kid, including when he came to every single one of his swim practices and cheered him on dressed as a different Hollywood starlet, Monica tells him that at least he showed up to every single one and cheered for him.
She then packs their bags and tells them they are going to Las Vegas to meet his father. Chandler and Monica arrive to the show of Helena Handbasket, who Chandler reveals to be his father. He begins to talk to the people in the crowd, and Chandler says he can't deal with this. This draws Helena's attention to him, and Chandler's father is surprised to recognize his son.
When do monica and chandler start dating
Helena then notices Monica's ring, and Chandler admits they are engaged. Rather awkwardly, Helena turns to another man and begins talking to him. Chandler interrupts and invites his father to the wedding, and his father tells him that he wouldn't miss it for the world. Ross makes everybody burst into laughter by threatening Chandler physically if he ever hurts his little sister.
What season does Monica and Chandler start dating?
Chandler suddenly freaks out thinking about becoming "Mr. He and Monica have their rehearsal dinner and after seeing his sexy celebrity mother and drag-queen dad, He freaks out even more, so he writes a vague apology note and runs.
Ross finds it and goes looking for Chandler while Phoebe and Rachel attempt to divert Monica, who is too wedding-high to notice anyway. Rachel and Phoebe find a positive pregnancy test in Monica's and Chandlers bathroom's Garbage. Rachel then distracts Monica while Ross and Phoebe look for Chandler and find him in his office, the reason he was hiding is because he is panicking about become the "Bings" and he'll make Monica unhappy and Brings Up Ross' failed marriages.
Ross gets him to do things one step at a time and he feels better. Later smoking in the hall, Chandler overhears Rachel and Phoebe about Monica's pregnancy test and starts to freak out again, but instead of running he gets her a present and decides that a baby isn't so scary at all. It's revealed that Monica didn't take any pregnancy test and is hinted that it's actually Rachel's instead. In Season 8 they settle in as a married couple.
Although earlier episodes imply Monica planned to try for children immediately after marriage, in their first year of marriage they focus on adjusting as newly weds, supporting Ross and Rachel with their pregnancy and comforting Joey about his new-found feelings for Rachel.
In the Season 8 finale, Monica jokingly suggests they start trying for children only for Chandler to take her seriously, admitting he's crazy about them and thinks they're ready.
Thrilled, they decide to start trying immediately.
At the beginning of Season 9 Chandler is forced to relocate to Tulsa for work. Initially Monica plans to go with him, but is offered her dream job in New York, and they organize it so Chandler only has to be in Tulsa for half the week, although they admit it will be hard living away from each other.
After several months of a long-distance relationship Chandler learned that he would have to spend Christmas without Monica and the other friends in Tulsa, or else be fired from his job. He comes to feel empathy for the employees underneath him who are clearly depressed because they want to be spending Christmas with their families and tells them all to go home. After a female colleague named Wendy decides to stay behind to help him, Monica calls him to wish him a merry Christmas, and when he makes the mistake of mentioning that Wendy has stayed behind to help him, Monica gets suspicious and grills him, and he ends up inadvertently making it clear that Wendy is pretty, but assures Monica he's not attracted to her and nothing will happen between them.
When Wendy then hits on him, Chandler politely rejects her, saying he's a happily married man and nothing can happen between them because what he has with his wife is great.
Wendy responds by asking him why he's spending Christmas with her instead of with his wife if what he has with his wife is so great. Realizing Wendy is right and that she's trying to seduce him, Chandler decides he's had enough of being away from his wife and quits his job and to get away from Wendy before returning home to spend Christmas with Monica and the rest of the group, much to their delight.
Monica supports Chandler while he's unemployed and encourages him not to go back to his old job but find something he's really passionate about.
She eventually helps him find an internship and subsequent job in Advertising. After a year of trying to conceive, Monica and Chandler are still unsuccessful.