11. Aurora

10. Ginger

9. Julie Graff

8. Missy Goldberg

7. Mary-Angela Tribbiani

6. Kathy

5. Jill Goodacre

4. Joanna

3. Monica Geller

2. And finally, Janice Hosenstein

Chandler got a bad rap for being the "undateable" one of the group, but in reality, while his girlfriends may not have been winners, he still had them...
Just another missed opportunity devastated by poor timing. Aurora was by far one of the most beautiful women Chandler ever dated and she had an aura of mystery about her that was intriguing. However, I cannot openly condone the behavior of a person who cheats on her husband and boyfriend — Chandler deserved better!
A relationship is meant to be built on trust and honesty, and accepting your partner's flaws is the key to any happy relationship. Sadly, Chandler could not get over her wooden leg, and she could not get over his third nipple so, while their relationship was hilarious, it never would've worked long term.
Sadly, Julie didn't get much screen time, but the two of them had a lot of history, going all the way back to summer camp. Their relationship started out a little rocky and suffered from a "slight" case of miscommunication, but both of them matured from their younger selves, and I saw bright things in their future. Besides, who doesn't love high school sweethearts?
Not only was Missy a beautiful woman, but she satisfied Chandler's fun and wild side. He was always a big supporter of music and I think they could've had a lot to discuss, from their experiences in college to Missy's band to bonding over the dorkiness that is Ross Geller.
Chandler was definitely breaking some best friend codes when he decided to pursue Joey's sister, but there is no denying that she came from a loving, fun, and close-knit family with good values. And clearly they were both willing to risk something big to be together...
Aside from the fact that she flat out cheated on Chandler and broke his heart, only AFTER cheating first on Joey, she also just played into Chandler's insecurities too much, making him always feel unworthy and inferior. She was really talented and knew how to laugh, but the foundation of their relationship was shattered right from the start.
The two were brought together by the powerful, unforeseen circumstances of an earthquake and spent a few magical hours together. She definitely always had good breath because of her stash of gum and she was definitely protective, as she leapt into action when Chandler was choking. If only these two had more time, what could have been?
Commonly known as Rachel's "eccentric" boss, she might have had some red flags, like when she handcuffed Chandler to her desk but, at the end of the day, she was a total girlboss. She was head of her department at Ralph Lauren, did not conform to arbitrary gender standards, and was always up for a good time.
People may be surprised to see Monica in the #2 spot, but there are just some aspects of their relationship that rubbed me the wrong way. Of course, the best friend falling in love stereotype was beautiful to watch and the two really did complement each other, but Chandler was not always one of her top priorities, and she had some flaws that were a lot for Chandler to take on.
Janice is ABSOLUTELY, no doubt in my mind, Chandler’s best love interest. Yes, she might have had a loud and abrasive personality and a few annoying ticks, but, all in all, she had the biggest and kindest heart, was fiercely loyal, and loved Chandler more than anything. She was always willing to go out of her way to prioritize him and the people and things in his life. Not to mention, the two always seemed to find their way back to each other. JANICE AND CHANDLER 4EVER!
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