5 best and 5 worst Ross and Rachel moments on Friends

Friends might not have been the cultural phenomenon it was without the increasingly complicated love story of Ross Geller (David Schwimmer) and Rachel Green (Jennifer Aniston) spanning the television series. From the pilot to the finale, Friends spends all 10 seasons getting these two lobsters together and then ripping them apart again and again ... much to fans' frustration and delight.

Ross and Rachel are meant to be together, of course, but there's always something standing in the way of their happiness — often, an obstacle of their own making. So, before the two can finally decide they'll stop being "stupid" (Ross' word, not ours), things get very, very messy with mixed results. Sometimes, their snafus are hilarious and even touching, while other moments between them are absurd and truly upsetting. To celebrate the saga that still makes us cry, for better and for worse, here's a look at the best and worst moments Ross and Rachel ever had on Friends.

Best: The prom tape

While Ross tells Rachel about his feelings for her in the pilot, it takes a long time for either of them to finally grab that proverbial "spoon." First, she has to find out that he's in love with her courtesy of an accidental truth bomb from Matthew Perry's Chandler — sure, she'd already known he had a crush on her for ages, but the L-word really gets her to feel something at long last. Then, Rachel plays the waiting game once Ross meets girlfriend Julie (Lauren Tom). Even Ross and Rachel's first kiss is sullied by scandal, since he's still with Julie and later makes that unfortunate pro/con list. All of these difficulties are worth enduring, though, for the scene in which the two realize they are each other's "lobsters."

Thanks to an unearthed video from prom in season two, Rachel discovers the hidden truth about the night that her date, Chip, shows up late to pick her up. If she'd paid attention to what Ross was up to back then, she might've seen him suit up in his father's tuxedo to save the day. That gesture didn't pay off at the time, but once Rachel sees his hurt and embarrassment on tape, she stands up, walks over, and plants their real first kiss right on his lips. The moment is near to perfect, bringing forth their long-awaited romance with just the right note of sincerity.

Worst: The 'we were on a break' up

While Ross is a thoughtful and emotionally generous boyfriend, his jealousy is downright crippling to his relationship with Rachel during season three. Whether or not his instincts about coworker Mark (Steven Eckholdt) proves to be correct, Ross' incessant presence at Rachel's workplace makes the situation untenable, especially once he begins to shame her for putting work needs over their date plans.

The breakup that results from that disagreement is perhaps one of the most arduously dramatic moments of the entire series. Rachel says she needs a "break from us" in a moment of pure frustration over his obsession with Mark, so Ross takes off to drown his sorrows at a bar, ending up in the arms of the fabled copyshop girl Chloe (Angela Featherstone). Despite his efforts to hide the truth the next morning, Rachel finds out, which leads to an even grimmer war of words between the two. If not for her vengeful pizza order and the comic relief of the quartet hiding in Monica's (Courteney Cox) room, this episode would be an easy skip-through for Ross and Rachel fans because it's uncharacteristically bleak for Friends. The fact that this scene is also the beginning of the never-ending "we were on a break" chant makes it even more eye roll-worthy to review.

Worst: The long letter

Rachel clearly prefers to keep Ross at arm's length most of the time while still teasing him that "it's never off the table," but, like clockwork, she can be counted on to sabotage almost every relationship he has with other women and then walk away from him again once the wreckage is complete. Such is the case in season three when he starts dating Bonnie (Christine Taylor), the feisty friend of Phoebe (Lisa Kudrow) who turns out to be a lot more intriguing — and has a lot more hair — than Rachel expects.

Rather than letting the new couple carry on with all the Strip Happy Days fun during the gang's beach trip, Rachel decides to meddle and convinces Bonnie to shave her head again. She then pretends to be friendly to her while informing Ross that she "maybe" wants to be with him again so that he breaks up with his new girlfriend. Of course, he does just that, but as soon as he sends Bonnie on her way, Rachel pulls out an 18-page letter for him to read, which demands that he accept full responsibility for what went wrong between them before. She probably knows it won't work; she even pats his face like a puppy as an added insult. Ultimately, the quick reconnect is a major letdown for those fans who want to see them reunite in a real way, without any pettiness.

Best: Hello, Mrs. Ross and Mr. Rachel

On the other hand, sometimes their childish antics prove to be pretty fun for fans, like when Rachel one-ups Ross with her ability to get out of speeding tickets, or when they both find out that they hate the park. Perhaps the seminal example of their wires crossing in the best way happens in season five, when Ross mistakes Rachel traipsing around naked in her apartment as a personal invitation as the two hang back from the gang's Las Vegas trip for a night. The next day, they spend the whole flight out west trying to embarrass each other, with Ross winning the battle by putting permanent marker on Rachel's face.

Once Ross realizes the prank has ruined Rachel's vacation, he tries to make it up to her by joining her for drinks in the hotel so she doesn't suffer alone. After they run out of beers and playing cards, they venture out together and drunkenly stumble into a chapel and get married. The scene is classic fun, of course, but their gasp-filled day-after discovery of what they'd done is just as ridiculous and enjoyable. The development also leads to some iconic bickering scenes about the status of their annulment, before their on-and-off romance inadvertently steals the thunder of Monica and Chandler's engagement night in season seven.

Worst: After the name swap

Before Ross and Rachel's short-lived marriage, Ross makes a quick commitment to Emily Waltham (Helen Baxendale) after knowing her for just a few weeks in season five — and Rachel only has herself to blame for them getting together. After all, she was supposed to take Emily, her boss' niece, out to the opera one night, but dumped her on Ross instead so she could pursue Joshua (Tate Donovan). Once she finds out they've developed a connection, Rachel's consumed by jealousy, making her previous speech to Ross about wanting each other to move on a complete farce. This culminates in a last-ditch flight to London to interrupt the nuptials, which does indeed have the desired effect, once Ross says Rachel's name during his vows to Emily.

Rachel later agrees to take Emily's place on her and Ross' honeymoon to Greece, but ends up going on the trip solo. If that wasn't humiliating enough, Rachel also decides to tell Ross she's still in love with him smack dab in the middle of his effort to patch things up with his new wife. That last part of the circus is especially annoying, because they both break into a fit of hysteria mid-sentence and give up on each other far too quickly to track with the rest of their relationship saga. It's an awkward and emotionless moment that doesn't have any payoff for any of the build-up that leads to it.

Best: The videotaped Europe story

Friends is always at its best when all six characters get together with some kind of competition underscoring their adventure of the day. One of the most unexpected examples of this happens when Ross reveals that he accidentally taped the night he and Rachel got pregnant during season eight. Ross, who's going through a dating dry spell at the time, is introduced to the seductive "Europe story" by Joey (Matt LeBlanc), who suggests he tape himself telling it so that he can get it right during his next date. However, the camera is still rolling when Rachel arrives to get help with sending out wedding invitations for Monica, and things heat up from there.

The gang is later fully convinced it was Ross who first made a move on Rachel, but the tape eventually proves otherwise, as she's shown breaking out that tryst-inducing travel tale herself, unaware that everyone knows the purpose of that story. The slow burn reveal is exquisitely timed for maximum impact and fits right in with the more lighthearted bits of humor about the pregnancy, including the whole "who's the father" mystery sweater bonanza and Ross' indignant reaction to finding out condoms aren't 100 percent effective as birth control measures. Even better, it subverts all expectations about how something like this might happen to the duo and reaffirms, once again, that their enduring attraction to one another is not at all one-sided.

Best: The pretend proposal

The Gellers' 35th wedding anniversary in season eight is both a bore and a chore for Ross and Rachel, as Ross' parents, Judy (Christina Pickles) and Jack (Elliott Gould), make them pretend to be married so they won't have to explain the circumstances surrounding their unplanned pregnancy to their more conservative friends. However, putting on a faux family face allows Ross and Rachel to share some tender moments that we rarely get to see otherwise, like Ross describing the thoughtful way he would have proposed to Rachel.

Some elements of their storytelling obviously goes way off the rails — with Rachel claiming they'd hired both Stevie Wonder and Annie Leibovitz for their wedding ceremony, and Ross saying he rode in on a motorcycle — but there's also a surprising amount of truth to be found in their night of lies. With the show nearing its endgame, fans needed these intermittent reminders of how right the two characters were for each other to keep the intrigue going. By putting them beneath a veil and allowing them both to fantasize about what their life might be like together as a married couple, it's both a service to audiences and a much-needed revelation for the characters themselves. It still takes a while for any of this to set in with Ross and Rachel, but their relationship foundation is still strengthened by this unlikely occasion.

Worst: The engagement ring

It would take an entirely different list to chronicle all the best and worst moments between Rachel Green and Joey Tribbiani, but his accidental proposal to her in the maternity ward during season nine would probably rank high among their most terrible scenes of all time. However, Ross' reaction to the mix-up is nearly just as awful. Rachel is fresh out of the delivery room after some very extensive labor and has just been treated to a hard lesson about life from Janice (Maggie Wheeler). Janice spooks her into believing that Ross will become an absentee father once he meets his next wife, and, given how little the audience sees of Ross' first child, Ben, it's understandable why Rachel might buy into that fear.

Meanwhile, Rachel and Joey have always had a reliable friendship, and they were already living together, so whether it's reasonable for her to accept his non-proposal is up for debate. However, none of it could possibly justify the way Ross decides to hold that against her and forego pursuing a romantic relationship with Rachel, despite his obvious feelings for her and the fact that she's just given birth to his child. Just when it seems that these two will stop putting invisible barriers up between them, a misunderstanding as pithy as this one stops all progress right in its tracks once again, much to the dismay of Ross and Rachel shippers.

Worst: Ross' manny-phobia

While Ross says many cringe-worthy things about gender and sexuality throughout the series, his treatment of the male nanny in season nine is one for the books. After interviewing a ton of potential caregivers for daughter Emma, he and Rachel are exhausted by their lack of options and become increasingly desperate to find someone who can be trusted to tend to their baby. That's when Sandy (Freddie Prinze, Jr.) arrives and proves to be absolutely perfect for the job — he has oodles of experience, a great temperament, and most importantly, is very good with Emma, Rachel, and even Joey.

However, Ross simply refuses to get past the fact that Sandy is a man and peppers him with questions about his sexual preference and taunts about his gentle demeanor. Upon seeing Sandy fit in too well with Rachel and the rest, Ross insists that the guy be fired, despite his many qualifications for the job. It's a juvenile and unmodern position for him to take, which is made even worse by the fact that he proceeds to lust over Molly (Melissa George), the female nanny who replaces Sandy. Despite being a father of two by then, Ross still has some growing up to do, and the fact that he upset Rachel so much by taking away the caregiver she's comfortable with is more than a little disappointing.

Best: She got off the plane

During Friends' final episodes, Ross goes through a lot of grief as Rachel accepts a job that will take her and their child to Paris indefinitely. He's not only staring down the barrel of losing both of the most important ladies in his life, he's also disappointed to find out that Rachel won't be giving him the same personal send-off conversation she's had with the others and that their unexpected hook-up is merely a goodbye for her.

Eventually, he decides to put aside his hurt feelings and tell Rachel that he doesn't want her to go, but Phoebe's erratic taxi-driving and flight-delaying stories about missing phalanges don't get Ross to the airport in time to stop Rachel from getting on the plane. "The Last One" sees him come home to find a voicemail from Rachel as she experiences a real-time realization that she loves him too, and when the tape cuts off, she's there at his doorstep, revealing that she did indeed get off the plane for him. After so many missed connections between these two, particularly when it came to airport scenes, it's pretty poetic that their story is book-ended by one last flight. Looking back, fans probably deserved to watch Ross and Rachel live in their bliss a bit more than this, but seeing them decide to finally put aside all of the histrionics and commit to one another for good is intensely satisfying.