Monica Geller (Courteney Cox) had a couple of notable habits on Friends, amongst them cleaning as if her life depended on it. She also had a bit of a sweet tooth and had shed a lot of weight. There was nothing sweet about Monica’s love life, however. Until she met Chandler, she dated a couple of guys. Here’s a complete timeline of Monica’s relationship history:
1. Paul The Wine Guy Made Up A Moving Sob Story
Monica was excited when Paul, The Wine Guy, finally asked her out. More excited were her friends, who’d heard a lot about him. Although Paul (John Allen Nelson) told Monica the little secret he kept was a fifth date kind of thing, he revealed it anyway. Ever since his divorce from his wife, he couldn’t bring himself to perform in bed. Monica fell for it, and in the end, it turned out that Paul The Wine Guy used the same line on other girls. Even Joey, the hook-up expert, was shocked that Monica fell for the lie.
2. Alan Was Monica’s Most Loved Boyfriend
It wasn’t the norm for Monica’s boyfriends to be loved. When Alan came around, however, he won the heart of every single friend. Ross (David Schwimmer) loved him for the way he made him feel. Though everyone was heavily invested in Alan (Geoffrey Lower), Monica wasn’t happy in the relationship. She broke up with Alan, much to the disappointment of all the friends. Rachel (Jennifer Aniston) already had plans of taking him to meet her parents at the time of the breakup.
3. Fun Bobby Was Just Not Fun Anymore
Fun Bobby (Vincent Ventresca) had earned a reputation for being the life of the party. He too, just like Alan, was loved for always lightening the room up. He turned out to have an alcoholic problem, downing three bottles of wine in a single sitting. Fun Bobby later showed up to Monica’s party in a somber mood. He was worn out. His grandfather had passed away two hours prior, and he couldn’t get a flight out until the next day. He had everyone at the party reaching for tissues. Everyone but Janice (Maggie Wheeler), who was busy being photogenic, thanks to her ‘Janice Cam’.
4. Young Ethan Was…Young
During a conversation with Young Ethan (Stan Kirsch), Monica learned that, until he was nine years old, he thought that ‘gunpoint’ was a place where crimes happened. He was charming to say the least. So much, that he and Monica ended up in bed. Only then did Monica learn the truth. Ethan, who’d previously revealed that he was a virgin, was not only an amateur at sex, but he was also underage. While he was happy that he’d had his very first sexual experience, Monica was devastated that she’d just hooked up with a high school senior.
5. Monica And Rachel Fought Over Jean-Claude Van Damme
The first time Monica saw Jean-Claude Van Damme, she was starstruck. She’d watched all of his movies, including one in which he ‘totally changed time.’ Rachel, on the other hand, didn’t think so highly of him. Rachel tried to link Monica and Van Damme, only for him to be interested in her instead. What resulted was a nasty rivalry that Phoebe (Lisa Kudrow) had to help break up.
6. Monica Broke Down When She Broke Up With Dr. Burke
Richard (Tom Selleck) and Monica were deeply in love. Though Monica’s parents thought it better for her to be in a relationship with Richard’s son instead, she shocked them when she unveiled him as her boyfriend on her father’s birthday. Soon, age would become an issue, since Monica wanted to have kids while Richard already had grown ones. When they figured out they couldn’t be together anymore, both of them went separate ways. Not even being friends who saw each other from time to time could help them come together again.
7. Julio Had A Way With Words
Julio (Carlos Gomez) worked at a diner in which Monica was also employed. Although she was hesitant to approach him at first, Monica did and found out that Julio loved to read, and was quite the poet himself. He had a habit of writing about things that moved him like shadows of trees, the laughter of a child, or Monica’s lips. Julio used Monica as his muse for a poem dubbed “The Empty Vase”. Phoebe had a different interpretation of the poem. She thought Monica was being referred to as an empty vase. Monica went on to give Julio a read of a lifetime, only for him to let her know she wasn’t the subject of the poem. He’d written the poem for all American women.
8. Pete Had A Dream Of Conquering The UFC
Peter Becker was the high-achieving man who gave Monica a heavy tip she likened to the tax of Romania. Pissed at the tech mogul, Monica went to his office to give him a lecture then ended up on a date. Though her friends loved Pete (mainly for his money), Monica found herself unattracted to him physically. With time, the pair did find their way into each other and officially became a couple. Their love came to an end when Pete had a dream of conquering the UFC and got himself beaten to a pulp.
9. Chip From High School Was Stuck In Time
When people think of their high school crushes, the expectation is that time would have changed them in a particular way. In the case of Monica’s high school crush, Chip (Dan Gauthier) who was popular back then, he seemed to have frozen in time. He lived with his parents, kept in touch with his high school friends, worked at the Multiplex, and had a curfew. Monica did date Chip from high school, except she was a grown-up.
10. Dating Dr. Burke’s Son, Timothy Was Awkward
Judy Geller’s (Christina Pickles) dreams came true when Monica finally met the person she had recommended, Dr. Burke’s son, Timothy(Michael Vartan). Except for Monica, it was an awkward Thanksgiving invite. Parts of the son reminded her of the father, forcing the two of them to call it off. Monica had met Timothy when she went to Dr. Burke’s place of work with an eye problem. It was ironic that she thought she couldn’t go to Dr. Burke’s without a boyfriend, yet she ended up finding his son attractive.
11. Chandler Was ‘The One’ All Along
At some point, Monica was worried that she’d end up all alone. Lucky for her, the one she’d been looking for had been there all along. She and Chandler (Matthew Perry) first linked up at Ross’s wedding in London. The two of them dated for a while, kept everything under wraps until it was safe for everyone to find out in their own unique ways. It was the happily-ever-after Monica had imagined.