When news broke of Matthew Perry’s untimely death, the world mourned one of the greatest comedic talents. Most celebrated for his role as Chandler Bing in Friends, Matthew’s sardonic wit and humor brought a much-needed honest charm to the series. And although he was “awkward and lonely and desperate for love,” he was also a heartbreaker in more ways than one.

In reality, Matthew was a charmer—Selma Blair and Gwyneth Paltrow remembered his flirtatious energy and quick wit. This charm peeked through his portrayal of Chandler, an archetype of an attractive man who needs therapy but instead uses humor as a defense mechanism. Of course, this led to many love interests for Chandler, some of whom we loved and some of whom may not have been the right fit. Luckily, he found his happily ever after with Monica, but only after many love trials and tribulations. So here’s our official ranking of Chandler’s girlfriends.

Best: Monica Geller (Courteney Cox)

We would be remiss if we didn’t make Monica Geller Chandler’s best girlfriend. Apparently, Courteney and Matthew’s chemistry was so good that, although writers hadn’t planned to pair them up, they decided to explore the option in Season 3. Fans loved them together after “The One With the Flashback” in which they share a long, intimate hug while Chandler comforts Monica.

In “The One With the Jellyfish,” the Season 4 premiere, Monica says that she wouldn’t sleep with him if he was the last man on Earth. But by the Season 4 finale, they’ve jumped into bed together, at first for comfort, and then for love. As their relationship develops beyond friendship, their sexual relationship turns into a romantic one, and we love that Monica is the one who gets Chandler to finally embrace commitment. We could go on and on with our favorite moments of the two of them, but they bring out the best in each other, becoming our TV mom and dad by the series finale.

Janice Litman-Goralnik (Maggie Wheeler)

Some people might say that Janice is the worst, but those people would be wrong. Janice is a strong and independent woman who knows who she is, and she takes no BS from Chandler or any of the Friends. While Janice is often the butt of jokes—her nasal voice and overbearing nature are pure fodder for sitcom humor—she is open and loving and teaches Chandler to embrace commitment. When she cheats on him with her ex-husband, it’s devastating (and a good reason to rank her lower), but this allows Chandler to let her go.

Marjorie (Christina Moore)

Marjorie is a sweetheart, so we have no complaints. The only issue is that she screams violently in her sleep, which obviously isn’t ideal for Chandler (or Joey). Even though it didn’t work out, she’s Chandler’s last girlfriend before he jumps into bed with Monica, so we don’t really mind that it doesn’t grow into a long-term relationship.

Nina Bookbinder (Jennifer Grant)

Nina is perfectly nice and perfectly sweet, but Chandler should have never dated her in the first place. When he’s faced with firing her, he makes her look crazy instead to save face. We don’t discover too much about Nina before she is gone, but she does not bring out Chandler’s best side.

Joanna (Alison La Placa)

Joanna and Chandler’s relationship is a weird one. She immediately crushes on Chandler, who goes out with her only to realize that she’s a “big dull dud.” But Chandler’s fault in the situation is that he’s not upfront with her. It’s okay that they’re not compatible! Then, Chandler bumps into her and they go out again. She locks him in her office with sexy handcuffs, which some people (including Chandler) might not like, but it’s hilarious, especially after how he treated her.

Aurora (Sofia Milos)

Aurora is the epitome of a hot, ethnically ambiguous woman who men believe is out of their league. She teaches Chandler to be more confident in himself and in his looks, but her polyamorous lifestyle doesn’t match up with Chandler’s desires. Although her time as an Israeli soldier and her unique background make her an interesting character, we can’t help but feel that she feeds into an archetype of the hot, mysterious, unattainable woman. And Aurora’s multiple boyfriends only heighten that characterization.

Jade (Brittney Powell)

Jade is definitely not Chandler’s ideal girlfriend. He basically tricks her into sleeping with him by pretending to be Jade’s ex, Bob, and then shows up as a shoulder to cry on when “Bob” stands her up. It’s definitely not a great look for Chandler, and Jade’s disinterest in Chandler after they hang out makes it clear that they’re not a good match.

Ginger (Sherilyn Fenn)

We love when Chandler gets the girl, but it’s not as fun when that girl turns out to be Joey’s ex. Of course, Joey acted weird about Ginger’s wooden leg, but Chandler rose above it. However, Ginger couldn’t get past Chandler’s third nipple, which is pretty hypocritical and shallow of Ginger. We love his nubbin!

Susie “Underpants” Moss (Julia Roberts)

Susie is so disappointing because we loved the potential for more of Matthew and Julia’s on-screen romance. Their chemistry was off the charts, mirroring their off-screen relationship. But we have to give it to Susie for getting her revenge on Chandler, who pulled up her skirt in elementary school (which led to her unfortunate nickname).

Worst: Kathy (Paget Brewster)

Kathy was the woman who changed everything for Chandler, but she also broke his heart the most. She started dating Chandler by cheating on Joey. Then, her relationship with Chandler ended because she cheated on him with her co-star. Despite showing Chandler that he was ready for a real relationship, which led him to Monica, Kathy is definitely the worst for breaking our boy’s heart.