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Chandler earned the nickname “Sir Limpsalot” from his friend Ross Geller after Monica Geller dropped a sharp knife on Chandler’s canvas shoe during a 1985 Thanksgiving and cut off the tip of his small toe. By the way, Chandler hates Thanksgiving because his parents announced their divorce on that holiday when he was nine years old. His dad came out of the closet and ran off with a man. 


Yo, paisan! [Joey]. Can I talk to you for a sec? Your tailor is a very bad man...Oh, come on. He said he was going to do my inseam, and then he ran his hand up my leg. And then, there was definite...cupping.

In the “Fears and Pet Peeves” department Chandler admitted that Michael Flatley, the Lord of the Dance gave him the “heebie-jeebies." Chandler justified his fear of this Irish folk dancer saying "His leg flails about as if independent from his body!" He also doesn’t like bra’s because he just can’t figure them out. And he hates dogs because “they’re needy, jumpy and you can’t tell what they’re thinking, and that’s scary!“ But, perhaps, the most disturbing thing Chandler ever saw was his dad doing tequila shots off the pool boy.

Smoking is another of Chandler's vulnerabilities. He quit for a while, but when he began to smoke again due to stress from work, his friends did not approve. In defense of his personal failure of succumbing to his addiction, Chandler angrily told his friends "Hey, you know, I have had it with you guys and your "cancer" and your "emphysema" and your "heart disease." The bottom line is smoking is cool and you know it." Of course, with pressure from Monica and friends, he stopped his nasty habit for good.

Phoebe: All right, y'know forget hypnosis. The way to quit smoking is to dance naked in a field of heather, and then bathe in the sweat of six healthy young men.


Or what my father called Thursday night.

For a time, Joey moved to his own apartment, and Chandler shared his digs with a giggling psycho named Eddie who entered Chandler's room at night to watch him sleep. Eddie was so loopy that he thought a goldfish-shaped cracker in the fish tank was a real fish. To finally get rid of him, Joey secretly moved back into the apartment and convinced Eddie that he’d never left and that Eddie was mistaken in his belief that he'd ever lived with Bing. Later, Chandler moved into Monica's apartment when their romance began to blossom while Joey remained across the hall.

Joey & Chandler relax in their lounge chairs
Joey & Chandler Watch TV in Comfort

Before Chandler fell in love with Monica he had an on and off relationship with an irritating, nasal girl named Janice whose catchphrase was “Oh...My...GAWD!” She called Chandler her "Bing-a-Ling." Janice eventually married, left her husband, had a fling with Chandler, got divorced and resurfaced a last time when she began to date Ross for a while.

Chandler also dated Kathy, Joey's actress girlfriend (Joey forced Chandler to live in a box as penance for dating her behind his back); Joey's ex-girlfriend Ginger the Stick Lady who unbeknownst to Chandler had an artificial leg (which Joey had accidentally thrown in a burning fireplace); Nina Bookbinder, Chandler's pretty office assistant whom he later labeled mentally disturbed; Joey's sister Mary Angela with whom Chandler shared a drunken smooch against Joey's wishes; Joanna, Rachel's boss at Bloomingdales who handcuffed Chandler in her office; Aurora, a married enchantress who only wanted to have wild sex with Chandler - and other men; and a woman in Atlantic City who turned out to be a man - that Chandler kissed.

Going back in time to his fourth grade, Chandler lifted up the skirt of Susie Moss during a play and the entire audience got a good laugh. Years later, Susie, now an actress, reunited with Chandler, lured him into a men’s room stall with the promise of sex and convinced him to strip naked and put on her hot pink thong panties. Susie quickly snatched up his clothes and left Chandler to walk home naked for making her live with the nickname “Suzie Underpants” until she was eighteen.

Another dating tale happened when Chandler was 15. It seems he went to summer camp for two years (his nickname was "Skidmark") and met and dated a girl named Julie Graff. However, when she got fat, he dumped her (this story upset Monica very much who was herself a former fatty).

In college, Chandler used to tell his dates he was a "Kennedy" to have sex with him. He also got drunk one night and slept with the woman who cleaned his dorm. This fact was inadvertently revealed during a heated conversation with his friend Ross.

Chandler’s wish list of celebrities that he would like to sleep with consists of Kim Basinger, Cindy Crawford, Halle Berry, Yasmine Bleeth and Jessica Rabbit. Chandler did have the pleasure of being trapped inside an ATM vestibule during a blackout with Jill Goodacre, a famous underwear model. When she offered him a piece of gum, Chandler said "Gum would be perfection" and then quickly loathed himself for saying such a dumb thing.

When Ross Geller traveled to England to marry Emily, everybody but a pregnant Phoebe went along for the event. But while Ross's marriage ceremony ended in disaster (he said "Rachel" instead "Emily" during the "I Do" portion of the ceremony) sexual sparks began to fly between Chandler and Monica who happily frolicked under the covers and in the bathtub in their hotel suites.

Chandler & Monica after consummating their relationship.

The afterglow of Chandler's first sexual encounter with Monica during their stay in a London hotel. 

On their return to the States, Chandler and Monica both decided to keep their romantic liaison a secret. Eventually, Joey learned about it but he was sworn to keep his mouth shut. But Rachel and Phoebe wiggled the truth from Joey and in the spirit of fun, Phoebe set out to seduce Chandler. But Monica realized that Joey had spilled the beans, and a very competitive Monica forced Chandler to play along with the seduction game. But just as the situation started to heat up, Chandler broke and declared his love for Monica.

In the end, everybody knew about Chandler and Monica, except for Ross who one day saw them making out while looking out his apartment window. Shocked, he cried "That's my Sister!" Thankfully, his initial anger turned into joy when he realized that Chandler really loved his sister. What could be better than having your best friend for a brother-in-law.  

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