10. The One With the Videotape
“Oh, there he is, the father of my child, the porn king of the West Village.”
In this episode, we finally get the lowdown on what led to Ross and Rachel hooking up. As they argue about who initiated it, Ross angrily blurts out that he can prove he’s right because HE HAS IT ON VIDEOTAPE! The friends watch the beginning of the tape to settle the debate, with hilarious results! There’s also the side plot of Monica and Chandler finding out that the amazing couple they met on their honeymoon gave them a fake phone number, which causes them to blame each other’s quirks for the snub.
9. The One Where Ross Finds Out
“And that, my friend, is what they call… closure.”
In this episode, we finally get the moment 2 seasons in the making: Ross and Rachel’s first kiss! That moment will forever warm my heart!
Ross has been dating Julie and things are going well. Rachel is going crazy seeing them together. Rachel goes on a blind date, and while drunk, leaves Ross a voicemail telling him that she is over him. After hearing this, Ross has to decide whether to stay with Julie, or take his shot with Rachel. They argue at Central Perk, and Ross storms out, only to return for this epic first kiss moment. All the feels! Unfortunately, the next episode snatches that happiness away as quickly as it gave it to us!
8. The One With the Rumor
“You were the hermaphrodite cheerleader from Long Island?”
This Thanksgiving episode introduces us to Ross’s friend Will, who was not only a very large person in high school, but also really hated Rachel. We find out that Will and Ross started the “I Hate Rachel Green Club” because she made them so crazy. For Ross, it was love, but for Will it was just flat-out hate!
In addition to the club, they also spread a rumor that Rachel was a hermaphrodite. Monica reveals that Rachel spread a rumor about Ross hooking up with the school librarian, which was actually true.
This episode guest stars Jennifer Aniston’s then-husband Brad Pitt. Pitt is adorable and hilarious in portraying his hatred for Rachel. Watching this one always makes me wish they were still together!
7. The One With Chandler in a Box
“It’s like inviting a Greek tragedy over for dinner.”
This episode takes place right after Chandler has just admitted to Joey that he kissed his girlfriend, Kathy. Joey has decided he wants nothing more to do with Chandler, even going so far as to saying he’s moving out. Chandler offers to prove how sorry he is by being locked in a wooden box for hours, like Joey was locked in the entertainment unit.
We also see Monica attempt to date Richard’s son, after she meets him in his office with an eye injury. The friends all think it’s disgusting (it is) and Monica and Tim both realize it themselves after they kiss.
The episode ends with Joey forgiving Chandler, and Chandler and Kathy becoming a happy couple…for now.
6. The One With All the Thanksgivings
“Sir Limps-a-Lot. I came up with that.”
In one of the most epic Thanksgiving episodes of the series, we get more flashbacks of young Rachel, Monica, Ross, and Chandler. We flash back to 1987, the first time Ross introduces Chandler to his family, and Rachel. We find out that Monica overheard Chandler call her “fat,” and was very hurt. At this point in the series, Monica and Chandler are still a secret couple, so he apologizes but can’t get too romantic about it. Then, we flash back to 1988, where Monica is now very thin and tries to get revenge on Chandler, but ultimately ends up injuring him and cutting off part of his toe.
I absolutely love seeing all the flashbacks of the characters. It gives a lot more insight to their lives, and the scenes are always comedy gold!
5. The One With the Proposal (parts 1 and 2)
“I thought…that it mattered what I said or where I said it. Then I realized the only thing that matters is that you, make me happier than I ever thought I could be. And if you’ll let me, I will spend the rest of my life trying to make you feel the same way.”
Oh, this episode…my heart! Watching Monica and Chandler’s engagement brings me to tears every time!
We get set up with a good two-parter here. We’ve just found out in the previous episode that Chandler plans to propose to Monica, and has shown the whole gang the ring. He plans a beautiful, romantic dinner, and just as he’s about to pop the question…RICHARD WALKS IN!!
Richard and his date end up joining them for dinner, so Chandler’s plan is thwarted. But because everyone thought he already did it, they are asking Monica questions that would hint towards an engagement. Chandler, wanting to throw her off the trail until he can find another time to propose, starts talking and acting like he never wants to get married.
Enter…Richard. He shows up at Monica’s restaurant, professing his love for her and his willingness to have more children. What’s Monica to do, when her current love is saying he never wants to get married, and her former love is ready to give her the world? What we ultimately end up with is Monica setting up a romantic surprise to propose to Chandler. Their love is so beautiful and the engagement is so romantic.
Not to mention, we get Joey, Rachel, and Phoebe at a silent auction, where Joey mistakenly bids on a sailboat thinking it’s a prize. Joey ends up owning a boat, with no sailing experience, which provides some comical moments in the next season.
4. The One Where Everybody Finds Out
“Oh, yeah? Well, you don’t know about Hugsy, my bedtime penguin pal.”
The cat is out of the bag! In this episode, Ross is trying to snag Ugly Naked Guy’s apartment after they discover that he’s moving out. Rachel and Phoebe go with Ross to check the place out, and when Phoebe looks across the street, she sees Monica and Chandler fooling around. Her reaction is priceless!
Though initially shocked, Phoebe calms down after Joey and Rachel reveal the two have been together since they hooked up at Ross’s wedding. Poor Joey, who has been keeping the secret for several months, is relieved that almost everyone knows. However, Rachel and Phoebe want revenge, and decide to mess with the duo by having Phoebe pretend to be attracted to Chandler.
Monica witnesses the flirting and figures out that they know. What ensues is a battle of wits between Phoebe and Chandler, as each one raises the stakes to see who will crack first. It all leads up to a cringe-worthy kiss, when Chandler finally breaks down and admits he’s in love with Monica. This episode is definitely one of the funniest of the whole series.
3. The One With the Embryos
“Actually, it’s Miss Chanandler Bong.”
In this episode, we see an epic battle between the men and the women, to see who knows each other better. Joey and Chandler believe they know Monica and Rachel better than they know them. This turns into a full-fledged trivia battle to see who knows whom the best, with Ross being the quiz maker and judge. The hilarity that ensues during this contest is epic.
The game ends in a tie, and Ross reveals the lightning round. At this point, the stakes are raised back and forth. Monica finally proposes that the guys get rid of the chick and the duck, whose excessive noise has been driving the ladies insane. Chandler and Joey accept the wager on one condition-that if they win, they get the girls’ apartment.
The competition is tight, until Ross poses the question “What is Chandler Bing’s job?” The girls can’t get this one right, and lose the bet, which results in the guys and girls switching aparments.
We also have Phoebe preparing to get implanted with Frank and Alice’s embryos. It’s revealed that the chances of conception are low, and they can only afford to do it once. At the end of the episode, Phoebe reveals that she’s pregnant, which gets everyone to stop arguing and start hugging!
2. The One Where Ross Got High
“What’s not to like? Custard…good. Jam…good. Meat…good.”
Another amazing Thanksgiving episode that packs a punch! As usual, Monica is hosting Thanksgiving, and this time her parents are coming. It’s revealed that Jack and Judy don’t like Chandler, so Monica has not told them that Chandler moved in. Chandler vows to win her parents over, and then they can tell them.
Rachel is put in charge of making dessert, and decides to make a “traditional English trifle.” However, the pages of the magazine she’s using are stuck together, and the result is half an English trifle, and half a Shepherd’s pie. Ross and Joey are trying to get out of there as quickly as possible so they can hang with Janine and her dancer friends, so they ask everyone to lie and tell Rachel the dessert is delicious.
Come to find out, the reason the Gellars don’t like Chandler, is because when the boys were in college, they caught Ross smoking pot, and he blamed it on Chandler. Monica and Chandler insist Ross come clean, so that they can reveal their relationship to her parents. When Ross refuses, Monica tells on him, and a wild exchange follows, with each of them outing the other on their secrets, including Monica and Chandler living together, and Ross and Rachel getting married in Vegas. This is one of my all-time favorite scenes of the entire series.
Fortunately, we end with the Gellars loving Chandler for “helping Ross through the drug problem” and “taking on Monica as well.”
1. The One With the Prom Video
“See. He’s her lobster.”
This episode finally gives us what we’ve all been waiting for: Ross and Rachel together.
Ross is still trying to earn Rachel’s forgiveness and get another shot, while she makes it perfectly clear that there is no chance. Meanwhile, Monica, who is struggling to find work, decides to ask her parents for a loan. When they come over to the apartment, they bring a box of some of Monica’s old things.
As all of the friends are at the apartment, Monica pulls out an old videotape from the box, which is the girls getting ready for their senior prom. Ross immediately begs them not to watch it, but everyone else is excited to see the old video.
This is the first time we see “fat Monica.” It’s also the first time we see Rachel’s pre-surgery nose. Both are hilarious!
As the video plays on, it’s looking a lot like Rachel’s prom date has stood her up. This prompts Judy to tell Ross that HE should take Rachel to the prom. Ross says no, and that she wouldn’t want to go with him, but his parents convince him. The video shows Ross coming out of his room in a tux and grabbing some flowers, just as the girls are headed out the door behind them, after Rachel’s date shows up. The video ends with Ross looking heartbroken.
Everyone turns to Ross, surprised and awed at his incredibly sweet gesture. And finally…Rachel walks right over to him and kisses him. This is by far my favorite moment of the entire series. The build-up was long and frustrating, but it was worth the wait to see these two lobsters finally find their way to each other!
Honorable Mentions: The One With the Truth About London, The One Where No One’s Ready, The One in Vegas (parts 1 and 2,) The One With Rachel’s Other Sister, and The Last One