The Ultimate Breakdown: The Real Reasons Behind Ross Gellar's 14 Failed Relationships in Friends

Summary

Ross Geller's love life is filled with unsuccessful relationships, including three failed marriages and numerous dating blunders.

Ross and Rachel's intricate relationship timeline solidifies their status as one of television's most unforgettable couples. Moreover, Ross's romantic involvements with individuals such as Carol, Julie, and Bonnie contribute an element of humor and intensity to his already chaotic love life.

Ross Geller, a beloved character among Friends fans, is famous for his tumultuous love life throughout the show's ten seasons. While his on-again, off-again relationship with Rachel Green stands out, Ross has had a total of twelve relationships, three of which ended in failed marriages. Some of these relationships were short-lived, but all were complicated by his lingering feelings for Rachel. Each relationship had its own memorable conclusion, adding to the comedic and dramatic elements of Ross's love life. Among the six Friends characters, Ross is particularly notorious for his romantic mishaps, often becoming the subject of jokes related to his failed marriages and dating blunders. However, it is his complicated and unforgettable bond with Rachel that truly leaves a lasting impression, solidifying them as one of the most memorable couples in sitcom history. In addition to his rollercoaster romance with Rachel, Ross's love life is further enriched by other women who contribute to the hilarity and drama.

14 Carol

The story unfolds in the first episode of Friends, where Ross Geller grapples with the aftermath of his breakup with his first wife, Carol. After Carol comes out as a lesbian and leaves Ross to live with her partner, Susan, Ross shares the tale with his close-knit group of friends. Just then, Rachel Green, Ross's high school crush and newly single after leaving her almost-husband, walks into the scene. Ross's affection for Rachel reignites instantly. Meanwhile, the complexities of Ross's failed marriage with Carol intensify when he discovers that she is expecting their child. Despite their past, the former couple manages to maintain a cordial relationship, as they co-parent their son, Ben, throughout the series.

13 Julie

In the final episode of Friends season 1, titled "The One Where Rachel Finds Out," Rachel learns unintentionally from Chandler that Ross is in love with her. Realizing that she reciprocates those feelings, Rachel rushes to the airport to welcome Ross back from his trip to China. However, her romantic reunion takes an unexpected turn when Ross emerges from the plane with his new girlfriend, Julie. Over the next few episodes, Rachel's jealousy intensifies, eventually leading her to leave a drunken message on Ross's answering machine. After finally confronting their feelings for each other, Ross and Rachel share a deeply passionate kiss at Central Perk. Ross ends his relationship with Julie in order to pursue a future with Rachel.

12 Rachel (Season 2)

After the heartfelt Central Perk kiss in Friends season 2, episode 7, "The One Where Ross Finds Out," one would expect smooth sailing for the blossoming couple. Regrettably, reality has a different plan in store. Rachel unintentionally discovers a "pros and cons" list that compares her to Julie, leaving her initially enraged. However, Rachel, in her kind-hearted nature, finds it within herself to forgive Ross, leading them to enter into a relationship. Alas, this newfound romance proves to be short-lived as Ross succumbs to the green-eyed monster and grows jealous of Rachel's male coworker. The final straw for Rachel occurs on their anniversary when Ross unexpectedly appears at her office, completely disregarding her requests for privacy. Faced with this violation, Rachel insists on taking a break from their relationship.

11 Chloe

Devastated by the news that Rachel desires a break from their relationship, Ross finds solace in alcohol and seeks comfort with Chloe, a local woman from the copy shop. The following morning, Rachel unexpectedly appears at Ross's apartment, expressing her desire to reconcile. Consequently, news of Ross's one-night stand eventually reaches Rachel, igniting the infamous "on a break" argument. In the emotional ordeal depicted in Friends season 3, episode 16, entitled "The One With the Morning After," Rachel ultimately concludes that terminating the relationship is the best course of action. Nevertheless, the question of whether Ross and Rachel were truly on a break, as well as who bears responsibility, continues to be a subject of heated debate.

10 Bonnie

9 Rachel (Season 4)

After ending his relationship with Rachel, Ross starts dating Bonnie, who happens to be a friend of Phoebe. In the season 3 finale of Friends, titled "The One at the Beach," Bonnie joins the group during a beach trip. Feeling jealous of Ross's new romance, Rachel manipulates Bonnie into shaving her head, hoping it will cause a breakup. This turns out to be one of the more audacious actions taken by Ross throughout the series, as he suddenly loses attraction towards Bonnie. When Ross discovers the real reason behind Bonnie's decision to shave her head, it sparks an argument that leads to both Ross and Rachel realizing that they still have lingering feelings for each other. With the combination of Bonnie's freshly-shaved head and Ross's unresolved emotions for Rachel, he ultimately decides to end the relationship with Bonnie.

After Bonnie's departure, Rachel decides to make a heartfelt gesture to win Ross back. She presents him with an extensive handwritten letter comprising 18 pages (front and back). The letter signifies that if Ross agrees with her standpoint, they can reconcile their relationship. However, Ross dozes off while reading the letter, yet pretends to have absorbed its contents in order to appease Rachel. Unfortunately, Ross's unnecessary deception leads to another heated argument once he realizes the gravity of what he had agreed to. Within the letter, Rachel explicitly states that she will only consider reuniting with him if he fully accepts responsibility and blames himself for the breakup. Ross's anger erupts as he unintentionally confesses to his infidelity, ultimately resulting in the Friends couple once again parting ways.

8 Cheryl

Ross embarks on a romantic relationship with Cheryl, a paleontologist, during episode 6 of Friends season 4, titled "The One with the Dirty Girl." However, his excitement quickly turns to disappointment when he visits her apartment after a date and witnesses the appalling state she lives in. Initially, Ross tries to ignore the unsanitary conditions and seeks advice from Joey on how to make the relationship work. In his usual style, Joey suggests that Ross tolerate the mess in order to be with such a gorgeous woman. Nevertheless, after a second encounter with Cheryl's dirty habits, Ross ultimately decides that he cannot overlook this dealbreaker, leading to the end of their relationship.

7 Emily

In episode 14 of Friends season 4 titled "The One with Joey's Dirty Day," Rachel requests Ross to escort Emily, her boss's niece, to the opera. Ross and Emily hit it off immediately and decide to get married quickly. Rachel goes to the wedding in London with the intention of confessing her love for Ross, but she ultimately decides against it. However, the wedding ceremony takes an unexpected turn when Ross mistakenly says Rachel's name instead of Emily's during his vows. Emily asks Ross to remove Rachel from his life, to which he initially agrees. However, it becomes clear that Emily still cannot trust him, leading to the end of their relationship.

6 Janice

Janice became well-known among Friends fans as Chandler's on-again, off-again girlfriend, characterized by a unique, nasal voice and an irritating laugh. In "The One With Chandler's Work Laugh," an episode from season 5 of Friends, Ross crosses paths with Janice during a difficult time in his life, following the news of Emily's intention to remarry. Despite always finding Janice annoying, Ross and she briefly go on a date. In a twist of fate, Janice abruptly ends their relationship, claiming that she perceives Ross as whiny and bothersome.

5 Rachel (Seasons 5 & 6)

"The One in Vegas: Part 2," the Friends season 5 finale, sees a trip to Vegas culminating in an unexpected wedding. Following a night of excessive drinking, Ross and Rachel wake up to the shocking realization that they tied the knot in a Vegas chapel. Initially, Ross promises to seek an annulment, but his fear of another failed marriage holds him back. Meanwhile, Rachel, understandably furious upon discovering their marital status, insists they pursue an annulment together. Unfortunately, their request is rejected by the judge due to their tumultuous relationship history, prompting Ross and Rachel to initiate divorce proceedings.

4 Jill

Rachel's youngest sister, Jill Green, makes her debut in "The One with Rachel's Sister," the thirteenth episode of season six of Friends. Jill reaches out to Rachel for help after her father threatens to cut off her financial support for purchasing a boat. Despite Rachel's attempts to be supportive, Jill proves to be spoiled and entirely unwilling to take responsibility for her actions. Fuelled by jealousy towards Rachel and her independence, Jill maliciously begins dating Ross. Unaware of Jill's true intentions, Ross naively falls for her charade and fails to see through her manipulative tactics aimed at getting closer to Rachel. Eventually, Rachel voices her discomfort about the situation, leading Ross to end things with Jill, who subsequently leaves New York.

3 Elizabeth

In Friends season 6, episode 18, "The One Where Ross Dates a Student," Ross embarks on a romantic relationship with Elizabeth, one of his college students. Right from the start, their dynamic as teacher and student, combined with their twelve-year age difference, presents challenges. Despite these obstacles, Ross initially finds joy in his forbidden love affair. However, others, especially Elizabeth's disapproving father, Paul, are far from thrilled. With time, the age gap becomes more evident as their contrasting lifestyles and priorities clash incessantly. Eventually, Ross decides to end the relationship, and in a final act of immaturity, Elizabeth retaliates by attacking him with water balloons.

2 Mona

Ross first encounters Mona in the season 8 premiere of Friends, titled "The One After 'I Do'." As their relationship blossoms, it is revealed that Ross and Rachel had a previous one-night stand which led to Rachel's unexpected pregnancy. Ross finds himself juggling both his romantic involvement with Mona and his responsibilities towards Rachel's pregnancy. Despite the ongoing complications, Mona remains remarkably understanding and supportive. However, Mona reaches her breaking point when Ross decides to have Rachel move into his apartment. Understandably, Mona is deeply upset by the entire situation, leading to a strained departure of the couple.

1 Charlie

In Friends season 9, episode 20, titled "The One With The Soap Opera Party," Ross comes across Charlie, a fellow paleontology professor. Ross initially plans to ask Charlie out, but Joey swoops in and starts dating her before he gets the chance. Although Charlie develops feelings for Joey, it becomes evident that they have little in common. Eventually, their incompatible nature drives Charlie into the arms of Ross. The ninth season wraps up with Ross and Charlie together, and they continue dating in season 10. However, their relationship hits a roadblock when Charlie decides to reconcile with her previous boyfriend, leaving Ross heartbroken.