All 18 Major Romantic Relationships on Friends Explained and Ranked By Normalcy (8 of 9)

Ross and Elizabeth (Season 6)

Ross’s romance with Elizabeth was a recipe for awkwardness. Their age difference caused tension, with the friends judging Ross for dating a student. Despite initial attempts to make it work, Elizabeth’s youthful priorities—and in particular her drunken Daytona Beach Spring Break Plans—caught with Ross’s desire for a more committed relationship. The imbalance led to a fizzle-out, but provided humor through Ross’s insecurities about dating someone younger.

Rachel and Paul Stevens (Season 6)

Paul (masterfully portrayed by Bruce Willis) was Rachel’s boyfriend when Ross was dating his daughter Elizabeth. Initially, their main problem was Paul’s emotional detachment, which Rachel found off-putting. She eventually got him to open up, but once he did, he couldn’t stop talking about his unresolved issues. If they had managed to handle Paul’s emotional outbursts healthily, they might have become a long-lasting couple on the show. Unfortunately, they couldn’t, and their relationship ended.