Friends: 10 Most Heartbreaking Episodes
7. The One With Barry And Mindy's Wedding (S2, Ep 24)
What's really interesting about this entry, especially coming from a writer from the generation of millennials, is realising how different the writing for this episode could have been had it aired in the modern day.
Richard was Monica's first real love on Friends, and we could see their genuine affection for each other throughout the course of the second season. Despite their apparent age gap, the two gel extremely well, overcome a number of personal challenges to be together, and many fans at the time probably thought they were going to go the distance.
In the season finale, the pair hit another struggle with their age gap, and eventually come to realise they want different things being in the different stages of their lives. At Barry and Mindy's wedding, the pair have one final dance while tragically declaring their love for each other, knowing their relationship is at an end.
Nowadays, relationships with age gaps are very common and it is sad to look on the pair's break-up as a consequence or even pressure of the times. Of course, we were all much happier seeing Monica end up with Chandler, but in the moment it was very sad to watch.