A couple of years ago, I started a new series where I ranked the love interests of the main Friends characters. I took a break from Friends for a while and I never continued the series, until now! If you’d like to check out my ranking of Phoebe’s love interests, click here! This time, I’m ranking the women that Chandler has kissed, dated, and married throughout the show. I hope you enjoy and let me know which one you liked the most!
Kathy (Paget Brewster) and Chandler (Matthew Perry) had fantastic chemistry and she had the potential to be near the top of this list. However, their relationship was rocky from the start, considering she dated Joey before him. With how they ended up together, Chandler accused Kathy of trying to do the same thing with her co-star, Nick (Craig Strong). After that accusation, instead of talking and working past their argument, Kathy just slept with Nick on a whim, which was revenge on Chandler, but also proving him right. That act of impulsivity ruined their reconciliation.
There was a lot of hope with Janice (Maggie Wheeler). She was sweet, fun, and she was very tolerant of Chandler’s shenanigans and fear of commitment. In the third season, he was even pushing past his fear of commitment for her, and it seemed like everything was going great. However, she couldn’t choose between him and her cheating ex-husband and in the process of choosing, she ended up cheating on Chandler. She could’ve been the one he ended up with. Instead, she knocked back his commitment progress and knocked herself down this list.
Susie Moss (Julia Roberts) had nothing but revenge on her mind. After he pulled a horrible childhood prank that left her traumatized, Susie saw Chandler Bing once again years later and started planning on her payback. Granted, the way she got him back was very clever. However, holding a 20 year grudge against someone? That’s just not healthy for anyone. She could’ve learned to forgive and let go or be honest with him and tell him she wanted nothing to do with him.
The first time Chandler dated Joanna (Alison La Placa), it was an awkward disaster. Chandler blew her off after the first date and she started to obsess over him, even wondering if Rachel (Jennifer Aniston) was the reason he didn’t call her. The second time they dated, things seemed fine until she cuffed him to her office chair and left to meet with her boss. True, she didn’t know how long she was going to be gone, but it was still a crappy thing to do. THEN, she got angry when he did the exact same thing to her. I can’t really blame her because he did it to her out of spite and left her cuffed all night. The relationship had a terrible start and an abysmal finish.
I had a hard time figuring out where to place Jade (Brittney Powell) on this list. I’m conflicted because she was manipulated into a date by Chandler and in a way, I believe Chandler got what he deserved. However, as someone who was unaware of Chandler’s actions, she wasn’t much of a saint. She couldn’t get over her ex and after having an intimate night with Chandler, she still contacted who she thought was her ex and completely bad-mouthed Chandler. Both parties in the relationship were sneaky and they were never going to work.
I liked Ginger (Sherilyn Fenn) until she became a hypocrite when it came to Chandler. When Chandler found out about her artificial leg, he was stand-offish at first. However, after talking to Ginger about it, he realized he was capable of not letting it ruin things between them. She unfortunately couldn’t return the favor. Once she realized he had a third nipple, she immediately left in disgust. I get the irony, but I’m still disappointed in her.
7. Chandler’s Co-Worker
There isn’t really much we know about Chandler’s co-worker, other than the fact he didn’t want to date her because she had a “big head.” From their one date, I’m already on the co-worker’s side. She seemed very sweet and fun, but Chandler’s judgment couldn’t let him just enjoy his date.
When it comes to Marjorie (Christina Moore), we don’t really know much about her either. All we know is that she talked (and sometimes screamed) in her sleep. She seemed to have a good personality and her and Chandler really got along, so to me she ranks higher on this list than most.
I really liked Nina (Jennifer Grant). She was pretty and had a lot of pep. She was done very dirty by Chandler. When told he was supposed to fire her, Chandler instead decided to ask her out. If that’s not bad enough, he lied and told his boss he couldn’t fire her because she “had a psychotic breakdown”. He might have had good intentions, but he ruined her reputation around the office (and possibly in the future when she was looking for another job) and kept her in the dark about the truth. He made selfish decisions and Nina didn’t deserve what he did.
4. Mary Angela
Poor Mary Angela (Holly Gagnier). While Chandler was mourning the death of his relationship with Janice, he got very drunk at Joey’s (Matt LeBlanc) birthday party, where he met and fooled around with Mary Angela. Now, I know more than anyone that you can say and do stupid things when you’re drunk. However, instead, of being honest with Joey and Mary Angela, he made things worse by going to her house and making out with her sister (who he thought was her). Mary Angela deserved better from the guy she was interested in AND her sister.
Danielle (Lynn Clark) was such a sweetheart. After a wonderful first date, Chandler didn’t hear back from her for various reasons. We’re led to believe she’s ghosting Chandler. The truth is she had Chandler’s number wrong the whole time. So after not being able to get ahold of him, what did she do? She tracked him down to make sure he was alright. That was such a sweet and selfless moment, and she deserved a lot better than Chandler suddenly being disinterested in her.
I really liked Aurora (Sophia Milos). She was honest and upfront with Chandler about what kind of relationship she wanted with him. For a while, it seemed like a sweet deal to Chandler. Even with multiple partners, she made sure to have time for him… it just wasn’t enough for him. They realized they both wanted different things and separated in a respectful manor. She even left the door open for him if he ever changed his mind.
There was no way that I wasn’t going to put Monica (Courteney Cox) at the top of this list. For starters, even at the start of the show, you can see how strong the chemistry is between them. When their relationship started out as just physical, neither side pressured the other for more. At one point, they both just realized they were ready for more. Sure, they had their rocky moments at the start, but it was never anything severe. Monica helped Chandler climb out of his commitment hole, and she forgave him for almost running out on their wedding. When he quit his job, she was very supportive and helped him figure out what he wanted to do in life. Even when they became a couple, they never stopped being best friends.