If one were to summarize the collective dating life of the main characters on Friends, nothing would make more sense than this:
“Married a lesbian; left a man at the altar; fell in love with a gay ice dancer; threw a girl’s wooden leg in the fire; live in a box!”
To write any successful sitcom, character progression is essential and a way of doing that is by showing them through their relationships. Chandler Bing is known to have the worst luck with women on the show. He most probably dated the least, partly because women mistook him as gay. And because he couldn’t get himself to stop talking stupid, even though he is a highly intelligent character.
Today we decided to count and rank every worst date that Chandler has had.
Aurora
Aurora and Chandler meet at Joey’s awful play. Aurora is shown to be a beautiful woman, or in words of Chandler, “She’s amazing. She makes the women I dream about look like short, fat, and bald men.” Chandler ends up going over to her and gets himself a date.
Aurora is Italian and pronounces Chandler’s name peculiarly. The two hit it off after their first date, except it turns out she’s married to Rick, and is going out with another man named Ethan. Aurora supposes she will mainly have a sexual relationship with Chandler, which is something he agrees to initially. However, Chandler objects to Aurora’s polyamory as soon as she adds Andrew to the list. And so he walks out saying it’s too hard.
Missy Goldberg
The least influential woman Chandler has ever been with- Missy Goldberg. We call her the least influential because she and Chandler never went out in the strictest sense of the term. In “The One Where The Stripper Cries,” it is revealed that Ross and Chandler, both liked Missy in college. So they made a pact between themselves not to go out with her. Except, Chandler broke the pact.
Chandler and Missy used to make out a lot, behind Ross’s back. Missy herself confesses she would go with Chandler to Ross’ turf, the science lab in the after-hours.
Mary Angela
Chandler’s dating history is brief, one because he and Courtney Cox’s Monica were woven into a beautiful romance in Season 5. The other reason being, lady luck never really shined upon him before. Mary Angela is one of those examples.
In “The One Where Chandler Can’t Remember Which Sister,” a wasted Chandler tries to get over Janice by groping Joey’s sister in the storage room. Only he can’t remember which sister. Moments of panic and confusion ensue, and Chandler deservedly gets punched in the face by Joey.
Janice
Janice was right, Chandler seeks her out. Throughout the series, Janice continually makes appearances as Chandler’s on-and-off flame. Janice is the woman Chandler has dated the longest, after Monica. The two shared quite an eccentric and lovable chemistry.
If Janice hadn’t gone back to her Mattress King husband in Season 3, things may have worked out between the two. Chandler grieved over her once she left, proving clearly she wasn’t as irritating as she was made out to be. She’s known Chandler the longest, heck they even found each other anonymously online, remember?
Ginger
One of the most progressive storylines of Friends is of Ginger and Chandler, albeit with a twist. Ginger dated Joey in the past, which was experience that didn’t turn out well for her. On a date night, Joey and Ginger happened to fall asleep in front of a fireplace. When it got cold, Joey woke up in the middle of the night to warm up the room by accidentally throwing Ginger’s wooden leg in the fire.
Chandler is unfettered by Ginger’s special ability. We wish it was the same from her side. The moment she sees Chandler’s third nipple, she’s out of his life.
Julie Graff
Chandler’s camp girlfriend, Julie Graff has resented him ever since they went out and he broke up with her. 16 years later, while eating at a restaurant, Julie happens to overhear Rachel raise a toast to the future Mrs. Chandler Bing, Monica. It’s appalling to learn why Chandler breaks up with Julie - she came back the third summer and she’d gotten really fat.
Because Monica has had similar childhood experience with Louis Posen, her best friend from fifth grade, she drags Chandler to apologize to Julie Graff. They track her down, and Chandler makes quite an apology.
Nina Bookbinder
You never dip your pen in the company ink, for you may have your hand stapled. Chandler fools around with a co-worker and a junior, Nina Bookbinder. After a dip in the company profits, Chandler is asked to fire a bunch of employees, with one them being Nina. Being the good boss, Chandler tells Nina he’s promoting her instead. He spins stories about not firing Nina to his boss. And when he finally has the real talk with her, Nina staples his hand before walking out the office.
Marjorie
Can’t really blame this one on Chandler. To be fair, Marjorie did scare the bejesus out of him in bed. Chandler and Marjorie meet at a sleep clinic, where he accompanied Joey. Although, she tells him, she’s in for talking in her sleep, she does more than that. The two shared a brief romance until Chandler is spooked by Marjorie screaming atop her lungs in sleep. So he does what’s for the best, and calls it quits.
Kathy
Kathy was one hell of a woman, for Chandler of course. Although she dated Joey, Chandler was smitten by her the moment he laid eyes on her at Central Perk. Of all the men in the world, Kathy had to be going around with Chandler’s best friend and roommate. When Kathy and Chandler shared a kiss at his apartment, their feelings were pretty apparent for each other.
They quickly broke up thanks to Chandler’s distrust over Kathy’s co-actor Nick. Chandler caught Kathy and Nick at her apartment and he never looked back again. Joey gave him a sympathetic hug though.
Susie Moss
Julia Robert’s Susie Underpants is Chandler’s nightmare on Friends. Susie spots Chandler at a movie set years after high school finished. And this time, she has an agenda. She indirectly encourages Chandler into asking her out on a date, with the latter oblivious to the fact that it is a setup. Then Susie coaxes Chandler into wearing women’s underwear before their date. At the restaurant, she signals him into the men’s toilet.
It’s very hard to process what happens to Chandler next. Not only does Susie make him strip, but she actually runs off with his clothes, leaving him in women’s underwear. Just a little payback for the fourth grade - Chandler’s high school misdeed. He’d lifted off Susie’s skirt and the whole class had laughed at her. She was Susie Underpants till she was 18!
Joanna
The only interesting plot in Chandler and Joanna’s romance was the fact that she was Rachel’s boss and made life miserable for her during the time she dated Chandler. Other than that, Chandler and Joanna had no chemistry, none what so ever.
The first time Joanna and Chandler meet, he dumps her and calls her a big, dull dud! But the second time, he’s genuinely interested in her and she appears to be bossing him around. Only Joanna locks Chandler in her office, without his pants and heads out for a meeting. Chandler parlays with Rachel to end things with her boss. In the end, Chandler gags Joanna’s hands instead.
