Suffice to say when Chandler and Monica both meet in the '80s, it is not love at first sight, at least on Chandler's end.A toe-severing was involved. 2. When They Almost Hooked Up. Monica and Chandler hooked up in the Season Four finale - The One in London. However, they didn't properly start dating until the start of Season Five. Monica and Chandler hooked up in the Season Four finale - The One in London. However, they didn't properly start dating until the start of Season Five. They each want to back out on the Vegas wedding, but neither of them wants to disappoint the other, so they decide they're going to leave it up to fate. As the ceremony is about to start, Joey barges in in his World War One outfit. With a month left before the wedding, Chandler and Monica faced the issue of their wedding vows. How do you hook up with your best friends mom? In what season of friends were Chandler and When did chandler and monica first hook up going to get married? On friends which season is it when joey and chandler swap flats with monica and racheal? It altered the show's dynamic, but didn't ruin it. The gang shares their worst thanksgiving stories and Chandler was upset learning the reason why he lost the tip of his toe. Moinca and Chandler get drunk and sleep together in Episode 24, Season 4. They say that they will stop once they leave London, but that fails and they begin a when did chandler and monica first hook up. Seeing Rachel and Ross disturbs both Monica and Chandler, and they start to think they're moving too fast.