In his memoir, Friends, Lovers and the Big Terrible Thing, Friends alum Matthew Perry reflects on his widely publicized romance with Julia Roberts and reveals what led him to break up with her. According to an excerpt published by The Times, Perry writes, "Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me ... So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."
Roberts appeared in season 2's "The One After the Super Bowl, Part 2" as Perry's character Chandler’s elementary school classmate, Susie Moss. Her goal was to seek revenge on him for pantsing her on stage during their fourth-grade recital. Besides Moss, Chandler had both brief flings and serious relationships on the show. While some of his exes are not that notable, Reddit thinks others are terrific.
Joanna
The first time Chandler dated Rachel's boss, Joanna, he dumped her because he thought she was "a big, dull dud." The second time was different on of their chemistry and penchant for adventure.
Redditor GingerFurball praises said love interest saying, "Joanna's 'hello Rachel' as she goes from the shower to Chandler's room is one of my favourite moments. I loved Joanna, she was a great character." They are correct, for Joanna came from a position of power, and certainly knew how to give people a piece of her mind, including the smart mouth, Chandler, himself. She was an accomplished woman and had she stayed on the show for long, she would have added a progressive story element by seeking an equal partnership with Chandler.
Ginger
In a Reddit poll asking fans to pick their favorite Chandler girlfriend, Redditor twothousandsteps remarks, "Maybe Ginger but she was hardly shown..." Chandler's girlfriend from season 3, Ginger had a bit of history with his roommate, Joey. They used to date, and once during their courtship, Joey woke up in the middle of the cold night to find fire they had built was dying out. Unbeknownst to him, he threw Ginger's prosthetic leg on the fire and ran away. Chandler was less than pleased with his roommates' behavior, as he'd genuinely begun to like the new woman in his life.
Ginger was witty and she made Chandler laugh. The first conversation that they had outside the men's room at Central Perk demonstrated that she had kind of the same sense of humor as him. They would have made a great pair had Ginger not freaked out on seeing Chandler's third nipple and run away. Though they had chemistry, the relationship needed time and mutual appreciation.
Susie Moss
In the same thread, Reddittor ibiZas_ remarks, "I really thought Chandler and Susie had a nice chemistry too." Chandler and Susie's tempestuous romance featured in the second part of season 2's post-Superbowl episode. They happened to bump into each other by chance on the NYC sets of Outbreak 2: The Virus Takes Manhattan. Susie and Chandler each had their own expectations in the relationship. He genuinely liked her and she was with him because she wanted to get revenge on him for pantsing her in grade school.
Eventually, Chandler did find himself in a sticky situation on Friends when Susie ran away with his clothes and left him high and dry in the bathroom stall. That said, Susie added a sense of adventure to their relationship. She got the best out of their brief, risqué fling, and it was she who helped build the momentum and transformed Chandler into a bit of an adrenaline junkie.
Aurora
In season 2, Chandler falls hard for a beautiful Italian woman named Aurora. Reddit VividTangerin "loved" her and Chandler together on Friends, and they comment, "He was so fun and romantic with her even though he, Ethan, and Rick weren’t enough to satisfy her."
Aurora and Chandler met at one of Joey's awful plays and the two of them hit it off right away. She entertained him with her adventurous stories and her sharp sense of humor. The only problem was that Chandler preferred to date one woman at a time and Aurora was polyamorous. Chandler heavy-heartedly called things off because he knew Aurora was a catch. She was honest with him from the very beginning and cherished his presence. Her wit and smarts make her one of Chandler's memorable exes on Friends.
Nina Bookbinder
Chandler dated a terrific woman and a co-worker named Nina Bookbinder in "The One With Two Parts, Part 1." They broke up because Chandler abused his position of power and, unbeknownst to Nina, retained her instead of receiving clear-cut orders to lay her off.
Reddit the worst bosses on Friends, and Nina definitely deserved much better than him.
Kathy
In season 4, Chandler felt a deep connection to Joey's girlfriend, Kathy, and she, in turn, reciprocated his feelings. Things, however, got a little messy when the two of them ended up kissing behind Joey's back. Since they were besotted with each other, it was only a matter of time before Joe gave his approval, and the pair dated for a brief while.
Redditor one of Chandler's best girlfriends on Friends.
Danielle
Chandler also dated a woman named Danielle early on in season 1's "The One With The Evil Orthodontist." He described their first meeting to his friends as "unbelievable" and "the greatest first dates of all time." Redditor David_Turck appreciates the character saying, "Was Danielle a wasted opportunity?" to which Reddit Jennifer_Mckenze writes back, "She’s good."
Both Redditors' are correct in their assessment because Chandler was quite enamored by Danielle. The fact that he said they could be totally themselves around each other and enjoy their time said a lot about Danielle's caliber and their chemistry. She was the perfectly good, sensible, and smart woman who Chandler wrongly fobbed off for being a "needy person," and there's no denying that she deserved more screen time on Friends.
Janice Hosenstein
A Reddit poll by Redditor Loonyluna66 asks s to share their opinion (via voting) about their favorite Chandler girlfriend, and in the comment section, a now-deleted Reddit writes, "I picked her [Janice] cause I love her, but I also think she was too good for Chandler. She is so sweet and funny, there’s no reason to dislike her other than her being loud."
They are a percent correct for Janice has undoubtedly emerged as a fan-favorite love interest. She breathed comic relief in episodes such as "The One With Barry And Mindy's Wedding" and "The One With The Candy Hearts." These and a couple more Friends episodes prove that Janice was Chandler's soulmate. She made him a happy man and genuinely loved him for who he was and who she hoped for him to be.
Monica Geller
In the same thread, Redditor BookWorm707 writes, "Janice was real funny for comic relief but as Monica was the best gf." Monica and Chandler are arguably TV's best couple. They demonstrated the importance of understanding and open communication in relationships.
Monica helped Chandler open up and gave him enough space to figure out his commitment issues. She stayed with him through thick and thin, treated him with love, and most of all, gave him an honest opinion whenever he asked for one.