the characters make many questionable choices on their journey to find "the One" (some a little more taboo than others).
But which were the most eyebrow-raising choices that Ross, Rachel, Monica, Chandler, Joey, and Phoebe made? Was it in their partners, their cheating... or Ross's need to propose to a woman after about a week and a half?
Dating Within Your Social Circles
Dating within your own circle can be both risky and rewarding (i.e Monica and Chandler). However, when Joey and Rachel briefly dated, it became clear that taking that step came with some risks.
Towards the end of season 9, Joey and Rachel begin to develop feelings for each other and, after a series of false starts, begin dating. This leads to awkwardness with Ross and, after some intimacy struggles, putting their friendship at risk. Thankfully, they realize that they aren't compatible and go back to being best friends.
Excessive Age Difference
Monica's relationship with Richard Burke is a prime example that age is not just a number. Not only is he a close friend of her father, but he is twenty-one years older than her. They eventually break up because of their differing opinions on having children.
The pair did genuinely love each other but, due to the age gap, they were in different places in their lives. Even though Richard tells Monica he is willing to have children to make her happy, it would only mean them both compromising on their values.
Not Wanting To Be Alone
Janice has been a recurring figure throughout the series, known for her grating voice and annoying personality. In season 1, she was dating Chandler. However, he struggled to break up with her multiple times due to her emotional reactions.
However, after he successfully ends things with her, he pursues her multiple times afterward just to avoid being alone. This includes asking her out on New Year's Eve (despite not enjoying her company) and having a one-night stand with her on Valentine's Day.
Student/Teacher Relationship
Ross has, without a doubt, struggled the most in the romance department out of all of his friends. However, his choices haven't garnered him much sympathy. In season 6, he is asked out by one of his students, Elizabeth Stevens. Despite the university's strict policy against teacher/student relationships, they begin dating.
By the end of the season, he realizes just how immature she is and breaks up with her. Due to their age gap and difference in life experiences, their relationship had little chance of going anywhere (her father's disapproval, notwithstanding).
Dating Your Ex-Girlfriend's Sister
In season 6, when Rachel's sister, Jill, comes to visit, she starts dating Ross to spite Rachel. Still harboring feelings for Rachel and not wanting to remove any possibility that they could get back together, Ross ends the relationship.
Having an ex-partner be in your social circle is awkward enough. But deciding to date said ex's sibling crosses a pretty important line. Not only was Rachel made uncomfortable by the situation, but Ross had to deal with the fact that he was being used.
Proposing Marriage After Six Weeks
Similar to Chandler, Ross struggles with being alone and, as a result, becomes much more impulsive with his romantic interests. This is made obvious with his second ex-wife, Emily. After enjoying a date (and enjoying an accelerated relationship), Ross proposes marriage after only six weeks.
This then leads to Ross saying Rachel's name during his wedding vows and Emily using an ultimatum that he must never speak to Rachel again. Because of Ross's haste to jump into another marriage, two people were hurt and humiliated.
"We Were On A Break!"
As much as this became a running gag on the series, it demonstrates just how damaging a lack of communication can be. In season three, Ross and Rachel decide to take a break from their relationship. However, after overhearing her co-worker at her apartment, Ross has a one-night stand with a woman named Chloe.
When Rachel learns about this, she accuses Ross of cheating while Ross maintains his innocence by claiming that they were on a break. They end up permanently breaking up as a result.
Pursuing Your Best Friend's Partner
Similar to dating one's ex-partner's sibling, pursuing one's best friend's partner also crosses a serious line. When Joey begins dating actress Kathy, Chandler begins to develop feelings for her (which she reciprocates). The pair share a kiss and, when Joey finds out, it almost destroys their friendship.
In the end, Chandler saves his friendship by getting inside a wooden crate at Joey's request. But this experience (as well as Chandler's subsequent failed relationship with Kathy) was not worth almost losing his best friend.
Accepting A Date To Get Back At Your Ex
Mark and Rachel's relationship begins shortly after her break-up with Ross in season 3. After comforting her through the breakup, Mark reveals his feelings for Rachel. After Ross annoys her over returning his stuff, out of spite, Rachel agrees to go on a date with Mark.
However, when she realizes her motivations for dating Mark, Rachel decides to not pursue a romantic relationship to not lead him on. This action is understandable given her emotional vulnerability, but it was still not the smartest decision.
Honesty Is The Best Policy
Dishonesty is the easiest way to break a relationship or, at the very least, land someone in an unpleasant situation. In season one, when Monica and Rachel swap names for health insurance reasons, it causes a lot of anxiety for Monica. It doesn't help that Rachel sets up a double date for the two of them with the doctors that are looking after her.
It leads to the date turning sour as the two friends begin to antagonize each other through bickering and exposing the other's embarrassing secrets.