Friends: Chandler’s Girlfriends, Ranked

There will never be another sitcom that has quite the same impact as Friends. The sitcom that followed the lives of New York’s funniest and most dysfunctional group of people ran for ten years, snatched a Golden Globe, and to this day is in the top 50 on IMDb’s list of top television shows. It’s hard to decide exactly what made the show so beloved by audiences, but truth is, once it enters your heart, it stays there.

Arguably, the best bits and plotlines of the show originated from the main characters’ love lives. Each of our fantastic six had their fair share of heartbreak and romantic adventures before reaching their happy ending. But not all of Chandler’s relationships were created equally… and some definitely weren’t that great!

Updated On Sept 24th, 2021 by Rose Graceling-Moore: Friends continues to prove hugely popular, with the reunion special attracting a huge audience (and shocking fans with the revelation that Ross and Rachel actually had a real-life crush on each other!). The focus remains on the big couples of the series, of course, but some of Chandler’s girlfriends shouldn’t be forgotten. 

10 Julie

Chandler’s love life was quite a complicated one. Not as complicated as Ross’s, but still, there’s quite a bit to unpack here. His first girlfriend was Julie Graff, a woman that Chandler dated at camp when they were both teenagers. Audiences later meet a grown-up Julie who wishes Monica luck in quite a sarcastic manner once she finds out she’s to marry Chandler.

Turns out, Chandler broke up with her because she gained over 100 pounds between summers, which angers Monica. Once he apologizes, it is revealed that Julie never knew why he broke up with her in the first place. There are no winners in this situation, but then again, they were still kids at the time.

9 Mary Angela

This one wasn’t technically a relationship, but it almost was – and affected Chandler’s relationship with Joey, too. More of a fling than anything else, she was also one of Joey’s seven sisters, which made the entire situation around Mary Angela ten times funnier.

Chandler knows he fooled around with one of Joey’s sisters, but he doesn’t remember which one because he was too drunk. If there’s a relationship that never happened because it was doomed from the start, then this is probably it. Fans can’t help but wonder what those potential Bing-Tribbiani babies would look like, though…

8 Susie

Susie Underpants, or Susie for short, was yet another childhood crush of Chandler’s. The two never dated when they were younger, and they parted on bad terms after Chandler pulled a prank on her and showed everyone at school Susie’s underwear.

When they meet again as adults, they actually begin dating. But it turns out the whole thing was just a revenge plot by Susie, who stole Chandler’s clothes in a public bathroom so she could embarrass him in return. She seemed like she would have been a lovely person, if she wasn’t hellbent on revenge.

7 Ginger

Ginger and Chandler have a short but cute relationship after he meets her come out of the bathroom in Central Perk. The two of them hit it off straight away and begin dating, and it seems like this will be a great partnership.

The twist here is that Joey used to date her… and threw her wooden leg into a fire. It was an accident, it was hilarious, and the whole thing became even more ridiculous when Ginger broke up with Chandler because of his third nipple. For her to leave him because of a small physical difference definitely doesn’t endear her to fans.

6 Joanna

One of Chandler’s most inappropriate partners was Joanna, Rachel’s boss at the time. After they go on a date, and in spite of Rachel’s hopes, Chandler decides he’s really not interested. But Chandler being Chandler, he keeps telling Joanna he’ll call her – but he never does.

Despite this, they later start dating, and things come to halt when the two are getting intimate in Joanna’s office and she handcuffs him in there without pants. While it was played off as hilarious at the time, fans now are unimpressed with this situation, Joanna leaving him there without his consent, and with him calling Rachel in to help him out, involving her, too.

5 Marjorie

Some of Chandler’s girlfriends were only around for an episode, and exist as a bit of a joke within the series – like Marjorie, the woman he met when he took Joey to a sleep study.

There was no reason to complain about Marjorie at first glance since she looked like an attractive, friendly, nice woman. The two seemed like they may have even had a future. That was, of course, until Chandler found out she screamed in her sleep. Unsurprisingly, he couldn’t quite handle that in a partner.

4 Aurora

Aurora was arguably one of the most beautiful women Chandler ever dated. Not only was she stunning, but she was also the picture of elegance, bravery, and mystery. Chandler was so taken by her that he honestly didn’t care when she revealed that she was polyamorous and she had a husband and a boyfriend while dating him.

This wouldn’t be an issue in and of itself, and Chandler told her that he was happy with the dynamic at first. However, it quickly became clear that Chandler wasn’t actually comfortable at all, and when she started seeing someone new, his jealousy became too much of a problem. Aurora was great, but she and Chandler were simply not compatible.

3 Kathy

Fans had great hopes for Kathy, as she was so cool, so sweet, so right. It was even forgivable that she and Chandler first fell for each other when she was dating Joey. If he could forgive Chandler for this, fans could too.

But then Chandler’s jealousy became a problem again, and the two started fighting over her friendships with other men. Then, after a fight, she slept with the man Chandler was jealous of, effectively ending things and breaking his heart. Kathy had the potential for being the best girlfriend Chandler ever had by that time, but jealousy and a lack of trust ruined this relationship.

2 Janice

Although fans (and the rest of the gang) didn’t like Janice’s laugh or voice, she was one of the best things that ever happened to Chandler. She wasn’t exactly the most likable person in the world, but she truly did love Chandler, and always managed to find her way back to him. And by season three, Chandler loved her too.

If it wasn’t for Janice realizing she was still in love with her husband, Chandler and Janice should have ended up together. It may not have been the perfect solution – far from it – but in a world where Monica doesn’t exist, perhaps Janice was the best thing Chandler could have.

1 Monica

Monica is the love of Chandler’s life, his best friend, his rock, and the two are arguably the best couple of the show. They may have taken a while to get together, but when they did, they were a phenomenal couple from start to finish.

They complement each other beautifully, plus, everyone is a sucker for two friends who eventually fall in love with each other. Monica and Chandler did have their ups and downs, and Chandler’s jealousy came up around Richard, but they always worked through it.