Friends is one of the best shows of all time. The popular NBC television series told the story of a group of friends living in New York City who struggled to work through friendships, getting older, careers and, of course, relationships. As such, we watched each and every character goes through several different relationships throughout the course of the series (some more than others, ahem Joey). Played by Matthew Perry, Chandler was one of the characters who went through several brief relationships before he finally met his match in Monica Geller. Here’s a definitive ranking of his 12 love interests:
12. Ginger
The storyline around Ginger is quite funny, especially when we learn she dated Joey first. She’s introduced in season 3’s episode “The One With Phoebe’s Ex-Partner” after Chandler meets her while walking into the washroom at Central Perk. When Joey finds out who Chandler is dating he starts to get nervous because the last time he saw her he’d accidentally thrown her artificial leg on the fire and then snuck out! Surprisingly, after a little coaxing Chandler is able to get onboard with the fact that Ginger is an amputee, but then when she finds out he has a “nubbin” (a third nipple) she gets totally freaked out and dumps him!
Warner Bros./Comedy Central11. Julie Graff
This relationship was all wrong, mainly because of the fact that Chandler was extremely shallow when he was younger. Chandler admits to Monica that he dated a girl named Julie Graff for two summers when he was 15 but shamelessly broke up with her after she gained weight. Unsurprisingly, Monica is shocked at his behavior and becomes worried he might do the same to her if she ever gained her weight back again. She forces Chandler to apologize to Julie, but it only makes it worse because she had never known the truth behind why he broke up with her!
NBC10. Margha
This isn’t the last time Chandler and Joey fall head over heels with the same woman, but it’s the first time we see it! In season 3’s “The One With The Football” they meet a Dutch woman named Margha. After hilariously arguing over who gets her, they finally decide to ask Margha who she wants to date. She chooses Chandler, but after she sees how he gloats in Joey’s face, she changes her answer to Joey! While Chandler didn’t necessarily date Margha, she was definitely one of his ‘love interests.’ But let’s face it, even if she had stuck with Chandler, it would never have lasted.
Warner Bros./Comedy Central9. Jade
Jade is a woman who Chandler basically tricked into dating him. She thought she was calling her ex-boyfriend, Bob, but really she was calling Chandler. He thought she sounded sexy, so he pretended to be Bob when he answered the phone. He subsequently set up a date with her at Central Perk as Bob knowing she’d be stood up which is when he planned to swoop in and sweep her off her feet! He ends up sleeping with her, but when she calls ‘Bob’ the next day to tell him she met another guy, he [Chandler] asks how the sex was and she replied with ‘eh.’ Ouch! These two parted ways amicably.
NBC8. Missy Goldberg
Technically Chandler never dated Missy, but he and Ross had a huge crush on her during college. Since they both liked her, they made a pact not to hook up with her in order to save their friendship. In season 10 they attend a college reunion and run into their old fling. By this time Chandler is married, but Ross is single, so he asks Chandler for permission to break the pact. Chandler tells him to go for it, and Ross later finds out from Missy that she and Chandler used to make out all the time! Sounds like these two had some serious chemistry back in the day!
NBC7. Aurora
Aurora was the first woman Chandler dated way back in season 1. Chandler met her in the audience when he went to see Joey perform in the musical drama “Freud!” The two go out on a date and Chandler falls head over heels. Unfortunately he finds out he’s not the only man in her life. She’s married to a man named Rick and has a lover named Ethan. At first, Chandler thinks he gets to have his cake and eat it too, but when she takes up an additional lover named Andrew, he quickly learns he’s not okay with having an open relationship, and so he ends things with her.
Warner Bros./Comedy Central6. Mary-Angela
While it might have worked for Rachel and Ross, it’s never a good idea to date a friend’s sibling, and Chandler proved this when he drunkenly hooked up with Joey’s sister, Mary-Angela. They kissed at Rachel’s birthday party, but the next day he couldn’t remember which one she was! After much convincing from everyone, Chandler realizes he has to go to Joey’s parent’s house and break up with Mary-Angela. He hopes that if he simply says her name, she’ll come forward. Sadly, it wasn’t that easy and he ends up revealing he has no clue which one Mary-Angela is. Joey gets even by punching him in the face! Safe to say that relationship was doomed to be a disaster.
© WARNER BROS. NBC5. Susie Moss
Susie Moss is one of our favorite guest stars because she was played by none other than Julia Roberts! The two meet in season 2, but actually have a long history together. Susie is Chandler’s classmate from the fourth grade. The two are reconnected when Chandler goes to visit Marcel on a film set. They decide to go out on a date together, but little does Chandler know, Susie has an agenda — she’s out for revenge. She holds a grudge from the fourth grade when Chandler lifted up her skirt. When the two are out for dinner, Susie tricks Chandler into getting naked in the bathroom and then steals all his clothes! We’re thinking if Chandler hadn’t embarrassed her back in the day, they might have actually been a good couple.
NBC4. Joanna
Chandler met Joanna through Rachel because Joanna was Rachel’s boss at Bloomingdale’s. Rachel sets them up on a date, but Chandler quickly realizes he’s not interested and one of the reasons is because she always has mascara goop in her eye. After much encouragement from Rachel, she finally convinces him to confront Joanna and dump her properly which he eventually does, but then hooks up with her again in season 4! Remember when Rachel finds Chandler handcuffed to the chair in Joanna’s office? Rachel forces Chandler to agree to never date her boss again because she doesn’t want it to jeopardize her job so that ended the Chandler and Joanna saga for good.
NBC3. Janice
Even though she was totally annoying at times, there’s no denying that Chandler obviously had a thing for Janice. They dated on and off throughout the early seasons of the show, and she continued to make appearances later on as well. We always knew these two wouldn’t end up together, but she definitely was Chandler’s first long-term relationship.
Source: NBC2. Kathy
If Kathy and Chandler had met under different circumstances they might have actually made a great couple. Chandler first met Kathy in season 4 when she was dating Joey. He developed a crush on her and she began to reciprocate those feelings emotionally until they eventually kissed (while she was still dating Joey). When Chandler and Kathy got Joey’s blessing and dated, she ended up cheating on him with her male co-star! Although these two had great chemistry, seems like she was a bit of a jerk. First, she cheats on Joey with his best friend, and then on Chandler!
NBC1. Monica
There is no doubt that Monica and Chandler were not only the best couple out of all their previous love interests but arguably the best on the show! They first hooked up in season 4 when the group travelled to London for Ross’ wedding to Emily. When their affair continued on long after they returned to NYC, it becomes clear these two are more than just a hookup. While they might seem like opposites, Chandler and Monica actually complimented each other really well. The series ended with them as a married couple who finally got to start their own family with two adopted kids, a pair of twins!
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