Ross and Rachel’s Turbulent History: A ‘Friends’ Timeline

Marisa Roffman

For more than 25 years, Friends has permeated pop culture, whether it’s the catchphrases (“How you doin’?”), iconic imagery (the fountain, the frame on the door…), or endless reruns, the show is still everywhere. And now, after a few months “on a break,” Friends is returning to streaming via HBO Max, as the new service debuts on May 27.

When it comes to unforgettable couples, Friends certainly had those, too. While Monica and Chandler eventually grew to be the show’s most solid pairing, Ross and Rachel’s drama was a part of the series from the very first episode, spanning the entire ten-season run.

However, despite a quickie marriage, child, a questionable break, and many, many close calls, the duo was only actually together for about a cumulative year in the show’s world. Let’s look back at the many ups and downs Ross and Rachel had through their turbulent history.

Long before they would hang out every day at Central Perk, a young Ross develops a crush on Rachel, who is best friends with his sister, Monica. Though this crush is not a secret, she doesn’t reciprocate his feelings, and neither act on it.

Though some of the pre-series information is murky at best — was Carol the only woman Ross slept with or did he also sleep with the college’s cleaning lady?! — a late-series flashback reveals that Rachel and Monica visit Ross at school to attend a party. Ross thinks he and Rachel share their first kiss in the dark; however, he really kisses Monica. Rachel, meanwhile, kisses Ross’ best friend, Chandler. (Revealed in season 10’s “The One Where the Stripper Cries.”)

The closest Ross comes to expressing his feelings is when Rachel is stood up for prom. His parents suggest he offer to take her — be her knight in shining armor — and he changes into a tux…only to discover that while he was getting ready, her real date showed up. (Revealed in season 2’s “The One with the Prom Video.”)

Eventually, Ross moves on and marries Carol.


At some point, Rachel and Monica become so estranged she doesn’t even get a courtesy invite to Rachel’s wedding to Barry. But that’s good news, because when Rachel becomes a runaway bride, she seeks out Monica for help and a place to stay. Ross, who just split from Carol, flirts with Rachel and hints he might want to ask her out. (Season 1, “The Pilot.”)

As Rachel struggles to take care of herself, Ross offers to teach her how to do laundry. Rachel kisses him when he helps her defeat a bully at the laundromat. (Season 1, “The One With the East German Laundry Detergent.”)

Ross, eventually, tries to tell Rachel how he feels, but she meets Paolo, a charming neighbor, during a city-wide blackout and is immediately smitten. (Season 1, “The One With the Blackout.”)


Paolo hits on Phoebe, which prompts Rachel to break up with him. In her distress, she accidentally reveals Ross’ baby-to-be (with his ex-wife, Carol) is a boy. (Season 1, “The One with the Dozen Lasagnas.”)

Though Ross is trying to date others, his affection for Rachel is never far. When she struggles with finding work, he lets her beat him at a high-stakes poker game amongst the group. (Season 1, “The One With All the Poker.”)

Rachel remains fairly oblivious to Ross’ feelings until her springtime birthday (continuity is again a bit murky here, given Rachel’s birthday was celebrated in February in the later seasons…) An out-of-town Ross leaves her a gift, which she discovers is both deeply personal and very expensive. The other friends are surprised by the gesture, but Chandler notes that’s what Ross does—like when he first fell in love with Carol.

Rachel debates if she should pursue something with Ross when he returns, and decides to pick him up at the airport…only to discover he’s returned to New York with a new girlfriend, Julie. Rachel doesn’t handle the reveal well. (Season 1, ”The One Where Rachel Finds Out”/Season 2, “The One with Ross’s New Girlfriend.”)

Eventually, Rachel jumps back into the dating pool, but it’s a mess. Her first night out is filled with talk about Ross and Julie, so her date suggests she needs closure. She borrows a stranger’s cell phone and leaves a message on Ross’ answering machine telling him she’s over him. Ross gets the message the next day while at Monica and Rachel’s apartment. The duo fight, but ultimately kiss. (Season 2, “The One Where Ross Finds Out.”)

To figure out how to untangle his messy love life, Ross makes a list of Rachel and Julie’s pros and cons. When Julie’s sole negative item is she isn’t Rachel, Ross realizes he needs to be with his long-time crush. However, when Rachel accidentally sees the list — including her cons — she’s furious and rejects him. (Season 2, “The One with the List.”)


Rachel moves on by dating Russ, who is basically a clone of Ross. When that becomes clear, she dumps him. (Season 2, “The One with Russ.”)

Ross doesn’t give up on Rachel, but her frustration with him grows. Phoebe encourages Ross that the two are destined to be together—Rachel is his lobster, AKA his soul mate. The point is proven true when the group watches an unearthed video of Rachel and Monica’s pre-prom activities, and Rachel sees that Ross was willing to be her prom date. They kiss and are officially together. (Season 2, “The One with the Prom Video.”)

The complication with dating someone you’ve been crazy about for more than a decade and also hung out with daily for the past year? It’s never exactly a casual relationship. For Rachel, that occasionally proves difficult, like when she realizes Ross has essentially planned out their entire future. (Season 2, “The One Where Old Yeller Dies.”) But outside of a few minor fights and disagreements, the duo is solid for the rest of the year.


Things take a turn when Rachel quits her job at Central Perk, and a friendly stranger, Mark, helps her get a job at Bloomingdale’s. Ross is immediately suspicious the man wants something out of it. (Season 3, “The One Where Chandler Can’t Remember Which Sister.”)

Ross goes overboard when Rachel has to work on their anniversary, and the bubbling tension finally explodes. Rachel suggests they take a break and the couple part ways. Ross goes out, but reaches out to Rachel… only to discover Mark has stopped by. Ross then sleeps with Chloe, the girl who works at the local copy store. (Season 3, “The One Where Ross and Rachel Take a Break.”)

Ross tries to hide his one-night stand with Chloe after Rachel says she wants to reunite, but isn’t able to cover his tracks. A devastated Rachel dumps him. (Season 3, “The One with the Morning After.”) The friend group is fractured in the immediate aftermath of the split, with everyone trying to manage their time with Ross and Rachel… but keeping them apart. (Season 3, “The One Without the Ski Trip.”)

Rachel attempts to date Mark (Season 3, “The One with the Tiny T-Shirt”) — much to Ross’ horror — but realizes it’s too soon to pursue a relationship. Rachel starts to soften toward Ross after he gives up being on TV to take her to the hospital for an injury. (Season 3, “The One with a Chick and a Duck.”)

Ross, meanwhile, starts dating Phoebe’s friend, Bonnie. (Season 3, “The One with the Ultimate Fighting Champion.”)

While the friends are out of town, Rachel and Ross get closer…until Bonnie unexpectedly show up. Rachel tells Ross she still wants to be with him. (Season 3, “The One at the Beach.”) Ross dumps Bonnie, but Rachel tells him before they can properly reunite, he has to read her 18-page (front and back!) letter. He falls asleep, and blindly agrees to her terms; however, he’s horrified to discover she actually wants him to take full responsibility for their breakup.

While Ross goes along with it for a bit, he eventually explodes, insisting they were both responsible for the demise of their relationship, and the two split again. (Season 4, “The One with the Jellyfish.”)

Ross and Rachel remain estranged for the rest of the year. Both have causal flings with others, but nothing serious sticks. The duo get into a fight at Thanksgiving when it’s revealed she returns all of her purchased gifts, but Rachel has the last word when she brings out a box of stuff she saved from touchstones in their relationship. (Season 4, “The One with Chandler in a Box.”)


Rachel makes her first real attempt for a relationship post-Ross with Joshua, a customer she meets while working as a personal shopper. (Season 4, “The One with Rachel’s Crush”) She is so enamored with him that she begs Ross to help her entertain her boss’ niece, Emily — who is visiting from London — so she has the opportunity to go out with Joshua. While it isn’t exactly the date Rachel expected, Ross and Emily instantly connect. (Season 4, “The One with Joey’s Dirty Day.”)

Though Emily’s time in New York is limited, Rachel throws her a surprise party in order to spend more time with Joshua, who eventually admits his feelings for Rachel. (Season 4, “The One with the Fake Party.”) Emily returns to London, but Ross proposes during one of her visits back to New York. (Season 4, “The One with All the Haste.”)

Rachel, upset over her ex’s engagement, proposes to Joshua, who understandably freaks out. Though she tries to make it right, the duo split. (Season 4, “The One with All the Wedding Dresses.”) Rachel decides to not go to the wedding (Season 4, “The One with the Invitation”), but when she realizes she still loves Ross, she rushes to London to stop him. However, when they come face-to-face, she simply congratulates him. But it’s enough to throw him: he says Rachel’s name instead of Emily’s during his vows. (Season 4, “The One with Ross’s Wedding.”)

Ross insists his slip means nothing, but Rachel isn’t sure how to proceed. He and Emily get married, but she instantly ditches him. (Season 5, ”The One After Ross Says Rachel.”) While he tries to reconcile with her, Rachel decides to tell Ross she loves him — although she at least has the presence of mind to realize it’s inappropriate and ridiculous after the fact. (Season 5, “The One with All the Kissing.”)

Emily, eventually, agrees to move to New York and reconcile with Ross… if he agrees to stop spending time with Rachel. (Season 5, “The One Where Phoebe Hates PBS.”) After Rachel encourages him to do whatever it takes to reunite with Emily — albeit without knowing the cost — Ross agrees, but the marriage is short-lived and they divorce. (Season 5, “The One with the Yeti.”)


Ross and Rachel manage to stay platonic for the first few months of the year, but things take a turn when an escalating prank war on their trip to Vegas leads to the duo getting drunkenly hitched. (Season 5, “The One in Vegas.”) Ross, worried about having three divorces under his belt at such a young age, balks at the idea of undoing the marriage, and decides to stay secretly married to Rachel. (Season 6, “The One After Vegas”/”The One Where Ross Hugs Rachel.”) Ross also takes Monica and Chandler’s decision to move in together as an excuse to suggest Rachel live with him, though she ultimately ends up moving in with Joey. (Season 6, “The One with Ross’s Denial.”)

An enraged Rachel does discover she’s still married to Ross, and given their history and the general post-wedding shenanigans, the former couple is unable to get an annulment and has to settle for a proper divorce. (Season 6, “The One with Joey’s Porsche.”)


Rachel’s sister, Jill, comes to visit, and a disagreement leads to Ross and Jill going out on a date. Rachel makes her discomfort with the situation clear, and Ross eventually breaks it off, because he realizes if anything was to progress with Jill, a reunion with Rachel would forever be off the table. (Season 6, “The One with Rachel’s Sister”/”The One Where Chandler Can’t Cry.”)

After Ross starts dating his student, Elizabeth, Rachel begins dating Elizabeth’s father, Paul. (Season 6, “The One Where Ross Meets Elizabeth’s Dad.”) Neither relationship ends well.

In reaction to Monica and Chandler getting engaged, Ross and Rachel decide to have a bonus night together, but the plans go up in flames when Monica catches the two kissing and accuses them of stealing her thunder. (Season 7, “The One with Monica’s Thunder.”)


Unbeknownst to the others (for several months), Ross volunteers to help Rachel mail out Monica and Chandler’s wedding invitations. When the duo reminisces about their almost-night together the previous year, Rachel comes on to Ross and they sleep together. (Revealed in season 8’s “The One with the Videotape.”)

Before Monica and Chandler’s wedding, Phoebe discovers a positive pregnancy test in Monica’s bathroom. Initially, she thinks the bride-to-be is expecting, but Phoebe eventually realizes Rachel is the one who is pregnant. (Season 7, “The One with Monica and Chandler’s Wedding”/Season 8, “The One After ‘I Do’”)

Rachel tries to keep the father-to-be’s identity quiet, but the gang snoop and piece together the clues they have, with a discarded red sweater being the biggest hint — which Ross claims, not realizing why it’s such a big deal. (Season 8, “The One with the Red Sweater”)

Rachel tells a flustered Ross about her pregnancy, and though he quasi-proposes, she shoots him down. (Season 8, “The One Where Rachel Tells…”)

As Rachel realizes her dating life is going to pretty drastically shift due to motherhood, Ross starts dating Mona, a woman he met at Monica and Chandler’s wedding. (Season 8, “The One with Rachel’s Date.”)


Joey develops feelings for his still-roommate Rachel (Season 8, “The One Where Joey Dates Rachel.”), which he feels increasingly guilty about as Ross misses more milestones in Rachel’s pregnancy. (Season 8, “The One with the Secret Closet.”)

Joey suggests the duo move in together; they do. However, that proves to be the final nail in the coffin for Ross’ relationship with Mona, who is out of town when he decides to move his pregnant ex-wife into his apartment. (Season 8, “The One with the Birthing Video.”)

Things get even more awkward when Joey admits to Ross he has feelings for Rachel, but Ross ultimately convinces his friend to tell Rachel the truth; Rachel turns him down. (Season 8, “The One Where Joey Tells Rachel.”)

Ross and Rachel’s relationship remains murky as she continues with her pregnancy, as she has difficulty when he nearly dates someone else (Season 8, “The One with the Cooking Class”) and the two avoid discussing what they’re actually doing together.

Ross’ mother, Judy, brings Ross a special gift at the hospital: a family ring to propose to Rachel with. Ross isn’t sure what he wants to do, but pockets it. After Rachel gives birth to their daughter, Emma, the duo kiss. But when Joey accidentally picks up the engagement ring box Ross has been holding on to, Rachel thinks he’s actually proposing — and says she’ll marry Joey. (Season 8, “The One Where Rachel Has a Baby.”)

Rachel struggles to tell Ross she’s engaged to his friend, while an exhausted Ross tries to work up the nerve to tell Rachel he wants them to start dating again. But when Ross realizes Joey didn’t just accidentally propose, Rachel also said yes, he’s upset and any thoughts about reconciling are abandoned. (Season 9, “The One Where No One Proposes.”)

The duo settle into life as platonic parents of Emma, but continue to skirt around resuming any kind of romantic relationship. But when a girls’ night out with Phoebe leads to Rachel giving a guy her phone number (Season 9, “The One with Rachel’s Phone Number”), Ross — who gets the call — is crushed to realize she may be moving on. He doesn’t give her the message.


Things boil over when Ross confronts Rachel after he spots her kissing her new coworker, Gavin. She realizes Ross kept the prior phone message from her, and admits their relationship isn’t working, so she moves back in with Joey. (Season 9, “The One with Phoebe’s Rats”/”The One Where Monica Sings”)

Rachel develops feelings for Joey (Season 9, “The One with Rachel’s Dream”), but he starts dating Ross’ crush, Charlie. (Season 9, “The One with the Soap Opera Party.”) While on a trip to Barbados, Joey and Charlie split, and they pair up with Rachel and Ross, respectively. (Season 9, “The One in Barbados.”)

Despite his new romance, Ross doesn’t handle the revelation that Joey and Rachel are dating well. (Season 10, “The One Where Ross Is Fine.”) He gives the duo his blessing, but Joey and Rachel realize they’re too close as friends to actually move forward romantically. (Season 10, “The One with Ross’s Tan.”)

Charlie and Ross manage to stay together a little longer, but she eventually dumps Ross when she reunites with her ex-boyfriend. (Season 10, “The One with Ross’s Grant.”)


Rachel leans on Ross when her father has a heart attack, and tries to sleep with him. Ross, however, worries about taking advantage of her vulnerable emotional state. Though Rachel is initially annoyed, she later admits a reunion is never off the table. (Season 10, “The One Where Joey Speaks French.”)

When Rachel loses her job, she runs into former colleague/almost-beau Mark, who suggests her for a job in Paris. (Season 10, “The One with Princess Consuela.”) Ross tries to frantically get her original job back, but resigns himself to let her leave when he sees how excited she is about the new opportunity. (Season 10, “The One Where Estelle Dies.”)

After Rachel says goodbye to everyone but him, an upset Ross asks why she couldn’t bother to bid him farewell. She admits it’s too difficult to say goodbye to him and the two sleep together. (Season 10, “The One with Rachel’s Going Away Party”)

Ross realizes he loves Rachel and races after her to stop her from leaving for Paris. When he catches up to her, she tells him he can’t have this conversation now and boards the plane. A heartbroken Ross returns home to discover a message from Rachel, who admits she loves him, too… and she needs to get off the plane. When the message ends, Ross is desperate to know if she was able to get off the plane — and as it turns out, she was. The duo reunites, for good, vowing this is it. (Season 10, “The Last One.”)

Marisa Roffman