Do You Remember All the People the "Friends" Characters Dated?

By: Susan McDonald
Estimated Completion Time
5 min
Do You Remember All the People the "Friends" Characters Dated?
Image: YouTube

About This Quiz

By the time "Friends" ended its 10-year run, all but one of the core characters were married or at least permanently paired off. It wasn't easy getting to that point though. See if you remember these unfortunate and often hilarious romantic missteps.
Monica dated a guy whose personality got considerably less enjoyable once he stopped drinking. Who was it?
Paul
Fun Bobby
Monica was enjoying her relationship with Fun Bobby until she expressed concern about the amount of alcohol he drank, so he got sober. Turns out Fun Bobby was fun for a reason.
Parker
Benjamin
Which character dated Phoebe's sister, Ursula, for a while?
Ross
Gunther
Joey
During the show's first season, Joey began seeing Ursula, Phoebe's identical twin sister. She didn't have Phoebe's kind heart though, and she dumped him without even a goodbye, leaving Phoebe to pick up the pieces.
Chandler
What well-known actor played Tommy, Rachel's short-term boyfriend who had a horrible temper that he showed only in front of Ross?
Ben Stiller
Ben Stiller appeared in the episode called "The One with the Screamer." He had a violent temper, but somehow no one except Ross was around when he displayed it.
Jon Favreau
Alec Baldwin
Matt Damon

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Who dated a girl whose apartment was a filthy mess?
Ross
During the show's fourth season, Ross went out with a girl who seemed perfect, that is until she invited him into her apartment. Trash, dirty clothes, old food, and even a rat living in a potato chip bag quickly put an end to the relationship.
Chandler
Richard
Joey
Chandler once was so anxious to get away from his girlfriend that he pretended he was moving to Yemen. Who was the woman?
Tracy
Kathy
Janice
Janice reappeared several times throughout the series. In a 1998 episode, Chandler had had enough, but he couldn't seem to shake her. Telling her he was moving to Yemen wasn't enough, because she insisted on going to the airport and watching him leave on his flight.
Phyllis
In the 1997 episode, "The One with Phoebe's Ex-Partner," who dates someone with a prosthetic leg?
Chandler
Chandler was upset when he learned that the woman he was seeing had a prosthetic leg, and it didn't help when he founds out that Joey once dated her too. It didn't end well, however, she ended up dumping him when she freaked out over his third nipple.
Monica
Ross
Rachel

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During the show's final season, Monica and Chandler are trying to become parents, but Joey's past love life threatens to interfere. Why?
There is a chance they will receive sperm he donated.
He slept with their adoption caseworker and never called her back.
When the caseworker arrives for Monica and Chandler's adoption home visit, she recognizes the building and reveals that she once slept with Joey and he never called her back. In the end, the unusually fast-thinking Joey turns the tables and accuses her of dumping him and breaking his heart.
He reveals their embarrassing secrets to the adoption agency.
He makes a pass at their surrogate.
During the show's fifth season, another character hooks up with Chandler's on-again, off-again girlfriend, Janice. Who is it?
Joey
Mike
Gunther
Ross
After learning that Emily is getting married, a depressed Ross ends up with Janice, who still thinks Chandler is in Yemen. Although he is impressed with her listening skills, eventually even she can't take his whining and dumps him.
During the season 1 finale, Joey is unable to have sex with his girlfriend because he is taking part in a fertility study. She is impressed with his gentlemanly ways and gives him an endless array of what product?
Fruit baskets
Melanie is unaware of Joey's predicament, but she is very impressed with his restraint and generosity toward her. She owns a fruit basket business and soon Joey's apartment is filled with gifts from his grateful girlfriend.
Condoms
DVDs
Framed photos

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Which character is revealed to be secretly married to a Canadian ice dancer?
Monica
Chandler
Phoebe
The gang is shocked to learn that Phoebe has a secret husband named Duncan. Thinking he was gay, she married him to help him get a green card, but he returns to reveal that his is straight and wants a divorce so he can marry another woman.
Joey
Who throws a fake party in order to invite someone they are hoping to date?
Rachel
After meeting a guy named Joshua at work, Rachel is having trouble getting him to ask her out because he is recently divorced. She throws a fake party as an excuse to invite him over, but it doesn't go well.
Ross
Monica
Chandler
What well-known actor played Parker, the overly-enthusiastic guy Phoebe took to the Gellers' anniversary party?
Ben Stiller
Ben Affleck
Alec Baldwin
Alec Baldwin was well cast in the season 8 episode, "The One in Massapequa." Parker loves everything from the plates to the food and even the Long Island Expressway, until his sunny disposition annoys even Phoebe.
Matt Damon

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Who dates someone who is so wealthy that going for a pizza means flying to Rome to get it?
Monica
Monica and her friends are more than a little impressed by Pete Becker's enormous wealth, especially because he is close to their age. The relationship goes well until Monica can no longer stand to watch him attempt to become the Ultimate Fighting Champion.
Phoebe
Chandler
Ross
During season 2, Monica begins dating Richard, a friend and contemporary of her father. What does he do for a living?
Opthalmologist
Richard Burke, played by Tom Selleck, is an opthalmologist. Monica becomes attracted to him when she sees him professionally and they begin a serious relationship.
Dentist
Pastry chef
Lawyer
During the show's third season, which character dates a man who keeps inadvertently exposing himself to everyone at Central Perk?
Phoebe
Phoebe is enjoying spending time with her new boyfriend, who is very athletic. Everyone is less impressed when he continually sits in positions that enable everyone to see up the leg of his baggy shorts, leaving nothing to the imagination.
Rachel's sister Amy
Rachel
Monica

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At the end of the show's third season, Ross is dating a woman named Bonnie, who seems perfect for him until Rachel takes matters into her own hands. What does she do?
Makes up a horrible lie about Bonnie
Convinces Bonnie to shave her head
Rachel is unconcerned when Phoebe fixes Ross up with Bonnie because the last time Rachel saw Bonnie, she was bald, but not anymore. During a weekend at the beach, Rachel convinces Bonnie that a shaved head was a great look for her, much to Ross' dismay.
Gets Joey to sleep with Bonnie
Offers Bonnie a job in Chicago
During the series, Phoebe dated two guys who carried badges for their jobs, which impressed her. One was a cop. What was the other?
An FBI agent
A security guard
A health inspector
When Phoebe began dating a health inspector, she was impressed at his ability to shut down a restaurant for health violations. She became less enchanted when it turned out they couldn't eat anywhere in the city.
A private investigator
Rachel and Danny were doing fine until she met his sister. Why did that end the relationship?
He and his sister were too physically familiar with each other.
In "The One with the Inappropriate Sister," Rachel is disturbed and confused when she sees how physical Danny is with his sister. She questions Ross and Monica about their relationship and they assure her that although they wrestled as children, they don't do it anymore.
The sister turned out to be someone Rachel hated in high school.
The sister made fun of Rachel.
The sister hit on Ross.

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Which two characters date a father and his daughter?
Monica and Chandler
Rachel and Ross
When Ross starts dating Elizabeth, a student in one of his classes, Rachel agrees to meet Elizabeth's father, Paul, and say good things about Ross. She ends up dating Paul, who was played by Bruce Willis.
Phoebe and Joey
Monica and Joey
During season 9, in an attempt to get Ross and Rachel to see how much they love each other, two of their friends set them up on the worst blind dates ever. Which of these things does Steve, Rachel's date, not do?
Cries
Tells her he is impotent
Says he is gay
Ross' date doesn't show up and Rachel soon wishes hers hadn't either. He's everyone's worst nightmare, sharing far too many hideous things about his miserable life.
Says he is in love with his boss
Ross once dated a girl who lived upstate. The train ride was so long that he fell asleep and ended up in Montreal. Where did this woman live?
Albany
Poughkeepsie
Ross was torn between a woman who lived in Poughkeepsie, who he really liked, and one who lived nearby, to whom he was not as attracted. The upstate romance fell apart when he missed his stop and woke up in Montreal.
Buffalo
Saratoga

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Phoebe once moved in with Gary, her cop boyfriend. Why did she move out the next day?
He shot a bird who was singing on the ledge.
Gary seemed like a great guy and Phoebe overcame her fears and agreed to move in with him. Their first morning together was blissful until he was bothered by a bird singing on the window ledge and promptly blew him away with his service weapon.
He was too much of a slob.
She found out he was secretly married.
The apartment was too far from Central Perk.
During season six, Joey began dating his hot new roommate, Janine. Why did they break up?
He cheated on her.
She cheated on him.
He didn't make enough money.
She hated Monica and Chandler.
Joey was thrilled when he began seeing Janine, but there was a problem they simply couldn't overcome. She despised Chandler and Monica, and Joey could not give up his best friends for her, regardless of how hot she was.
What was the name of the Italian stud Rachel dated during the show's first season?
Marcello
Paulo
Ross' high school crush on Rachel went into high gear when she moved in with his sister, but his plans to ask her out were quickly thwarted. She began dating a guy named Paulo, who spoke very broken English, but he had other assets.
Francesco
Gianni

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Which friend dated someone who claimed to be a senior in college, but was really a senior in high school?
Joey
Monica
In an episode called "The One with the Ick Factor," Monica was a little nervous about dating a guy several years younger than she was, but she was in for a big shock. After they slept together, he confessed that he was, as he had claimed, a senior, but in high school, not college. Ick indeed.
Chandler
Ross
Who dated someone who looked and acted exactly like the ex with whom they had just broken up?
Monica
Chandler
Rachel
After things didn't work out with Ross, Rachel moved on, or did she? She began seeing a guy named Russ, who not only looked like Ross, but also displayed all his personality traits.
Phoebe
Chandler once dated Rachel's boss, Joanna. Why did that relationship end?
He told her he was moving to Yemen.
She handcuffed him to a chair in her office.
Chandler overcame his revulsion to the mascara goop Joanna always had in the corner of her eye, but he finally hit his limit when she handcuffed him to an office chair while she went out to a meeting. Did we mention he wasn't wearing pants?
He got angry when she threatened to fire Rachel.
She embarrassed him at an office party.

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Monica finally got a chance to date the hot guy she'd had a crush on in high school. What was his name?
Chip Matthews
Monica was thrilled when she had a chance to date her high school crush, but it didn't go as well as she'd hoped. Turns out Chip never really left high school, still working at the movie theater and hanging out with his old buddies.
Biff Malone
Jerry Atkins
Austin Morgan
During the show's first season, Monica and Rachel date two cute doctors they meet when Rachel sprains her ankle. They are played by actors who played doctors on another hit NBC show. What was that show?
St. Elsewhere
Chicago Hope
Scrubs
ER
When Rachel sprains her ankle taking down Christmas lights, Monica takes her to the hospital, where they meet doctors played by George Clooney and Noah Wyle. The actors were then starring as Doug Ross and John Carter on the hit drama, "ER."
Monica once had trouble firing a troublesome sous chef because one of her friends was dating that person. Who was the friend?
Phoebe
During a season 8 episode, Phoebe begins dating Tim, who is Monica's sous chef. He's a bad sous chef, though, but Monica can't fire him because of Phoebe, until Phoebe decides to dump him.
Chandler
Ross
Rachel

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How did Rachel meet Tag?
At the coffee shop
He was her assistant.
Tag had no experience when he interviewed to be Rachel's assistant, but she hired him based on his looks alone. They dated for a while, but when she turned 30, she realized the age factor was too much and he was too immature for her.
Monica introduced them.
He was a blind date.
During season 6, Ross briefly dated one of Rachel's sisters. What well-known actress played that sister?
Christina Applegate
Reese Witherspoon
Christina Applegate played Rachel's sister, Amy, but Ross dated Jill, who was played by Reese Witherspoon. Needless to say, Rachel was not too happy about the pairing.
Rachel Bilson
Julia Roberts
Why did Ross's marriage to Emily end so abruptly?
He said the wrong name during their wedding.
The wedding was going pretty well until the vows began. When Ross said Rachel's name instead of Emily's, the ceremony proceeded but the marriage did not.
She refused to move to New York.
He refused to move to London.
He found out she didn't want children.

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During the episode, "The One in Barbados," Phoebe must choose between Mike and another man who wants to marry her. Who is it?
Rick
Gary
David
David the scientist is in the middle of proposing to Phoebe when Mike suddenly appears. Having overcome his fear of marriage and commitment, he declares his love for Phoebe and she chooses him.
Jesse
When Joey wants to impress Charlie, who is a smart, cultured scientist, where does he take her?
The Museum of Natural History
The Metropolitan Museum of Art
Charlie wants to go to the Met, and once Joey realizes she doesn't mean the Mets, he gets advice from Ross so he won't seem so dumb about art. Unfortunately, he turns in the wrong direction when they enter the museum, so his carefully prepared commentary on the collection makes no sense.
The Frick Collection
The Museum of Modern Art
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