Monica and Chandler are one of the most beloved couples in Friends, but one detail related to Monica’s ex-boyfriend, Richard, makes her relationship with Chandler weird. Created by David Crane and Marta Kauffman, Friends debuted on NBC in 1994 and came to an end in 2004 after 10 successful seasons and lots of unforgettable moments and jokes. Friends became one of the greatest TV shows of all time, and its main characters went on to become part of pop culture.
Set in New York City, Friends follows the lives of a group of six young adults who did their best every day to juggle their social, personal, and professional lives while also dealing with everything adulthood threw at them. Over the course of 10 seasons, the audience saw Monica, Chandler, Phoebe, Joey, Rachel, and Ross go through all types of obstacles as well as a lot of heartbreak, as it took them all a while to find their “lobsters”. Perhaps the one who went through one of the toughest emotional rollercoasters in her personal life was Monica (Courteney Cox), who had two serious relationships in Friends: first with Richard Burke (Tom Selleck) and later with Chandler (Matthew Perry), whom she eventually married.
Monica’s relationship with Richard began in Friends season 2 and it was controversial for those closest to them as Richard is 21 years older than her. Still, their relationship was a serious and committed one, but unfortunately, it couldn’t last for long as they had different plans for their future, mostly as a result of their age difference. Monica had a hard time getting over their breakup, and in season 3, they decided to be “friends with benefits”, but that didn’t last long. In that same episode, while Monica and Richard are making out, a song plays in the background, and that same song was used in two other Monica-related moments, but now with Chandler in the mix, which ends up making Monica and Chandler's relationship weird.
The song playing while Monica and Richard make out in Friends season 3 episode “The One Where Monica and Richard Are Friends” was later used in two Monica/Chandler scenes: first when they are making out in Monica’s apartment in season 5, and the following season when it’s revealed that Chandler is going to propose to her. Given the importance of Richard in Monica’s arc, how much she struggled to get over their relationship, and how he almost stopped Chandler from proposing to her, it feels odd that Friends reused a song that played during Monica and Richard’s final encounters in two scenes with Chandler, especially one as important as the reveal of his plans to propose to her. A detail as simple as this could imply that Monica never fully got over Richard, though that ultimately didn’t stop her from finally forming her own family and having the happy marriage she dreamed of.
However, this could also be seen through a less weird lens, with the song instead simply accompanying some key moments in Monica’s love life, such as her final moments with Richard (before she finally realized their relationship could never work as she would like it to), the beginnings of her relationship with Chandler, and the big step Chandler took when he decided to propose, as he was the one character in Friends who was scared of commitment. This song being reused in those specific scenes related to Monica doesn’t really seem like a coincidence, but in the end, it's the audience who will give it a meaning depending on their perspective of Monica’s relationships.