Crazy Ex-Girlfriend started off with Rebecca Bunch dropping her life in New York City to move to West Covina, California to be with her ex-boyfriend (Josh) from high school.

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The problem is, she moved to the small town on a whim and did everything in her power to reinsert her life in her ex's. Along the way to claiming Josh's heart, Rebecca had her fair share of lovers along the way, and let's just say they weren't always winners.

Greg’s Dad

In the third season, Rebecca does everything she can to find Greg after he lowkey disappears to attend business school. After a long day of soul searching, Rebecca receives a butt-dial from Greg and realizes his dad is sitting at the same bar she is.

After a long heart-to-heart, Rebecca goes home and sleeps with Greg's dad. Because sleeping with your ex-boyfriend's dad out of sadness is always a good idea...

Robert Donnelly

Robert Donnelly was Rebecca's former Harvard professor. As a married man, his affair with Rebecca ended horribly when she tried to burn down his house. This little secret hung on Rebecca's shoulders for most of Crazy Ex-Girlfriend.

When the name Robert was brought up, Rebecca said it was the name of a dog she used to have; in reality, he was the reason behind most of her relationship and mental issues.

Trent Maddock

Ah, Trent. It's later in the first season that viewers learn about this offputting man. In an effort to prove to the gang that Rebecca had a boyfriend, she told everyone she was dating a former classmate of hers who lived in the area. As it turns out, the man they chose as her fake boyfriend, Trent, had a real-life obsession with Rebecca.

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Trent became obsessed with Rebecca's life and did every creepy thing he could to implement himself in it. And while they technically never dated in real life or slept together, their strange fake relationship was enough to include him on this list.

Jason From Tinder

With Rebecca upset over Josh, she joins Heather in an attempt at Tinder. The two start browsing the app when they land on a guy named Jason. He's an attractive man who meets Rebecca at the bar and she ends up going home with him. However, the two never slept together because he wasn't a "healthy choice" for her.

Years later in season four, the two bump into each other where they date briefly. After all, it was about time Rebecca dated someone she didn't work with or wasn't friends with. However, this ended as quickly as it started.

The Vegan Guacamole Guy (Xander)

In the first season, Rebecca and Greg are trying to have an authentic and honest relationship. They start by going on a date to a Mexican street festival. With the smell of tacos filling the street, Rebecca runs into an attractive hipster, Xander, while she's comparing guacamoles.

Although she had the best intentions with Greg while on the date, Rebecca had a moment of panic and fled the scene to sleep with the hipster. If that sounds bad, it gets worse. Greg shows up at her door where he sees Xander leaving Rebecca's apartment. We never see the hipster again but it's safe to say this was a bad decision.

Josh

Ah, the man who started it all! Rebecca won't like hearing this but Josh was never the man for her. She literally left a job that was making her half-a-million dollars a year for a man she dated in high school for a summer.

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Their relationship was never based on truth. Rebecca lied about her reasons for moving to West Covina and morphed her way into Josh's life whether he liked it or not. The only good thing that came from Josh and Rebecca was that the latter made Josh think more about the world. Her bright mind made him realize that he should have never been with Valencia and he had no real career goals. This inspired him to do better. But on Rebecca's side, Josh's mere presence drove her insane.

Warren

Yes, a guy Rebecca slept with in college was a better match for her than Josh.

In the episode "Josh Has No Idea Where I Am!," Rebecca is flying back home to New York where she starts thinking back to her past relationships. While in college, Rebecca joins a drama program where she rehearses for Moby Dick. It's there that she falls for the director Warren; a senior who has a superiority complex.

After sleeping with each other, Warren promotes Rebecca from Fish #3 to Fish #2, proving that she was sleeping her way to the top from a young age and didn't even realize it. By the end of the episode, Warren was sleeping with other women, which was enough to push Rebecca out of the drama program.

Greg Serrano

Santino Fontana as Greg in Crazy Ex-Girlfriend Season One

The relationship between Greg and Rebecca is an interesting one. Rebecca met him when she first moved to West Covina and as it turned out, he was close friends with Josh. In Rebecca's own cooky way, she used Greg to get to Josh but Greg saw right through her act.

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As time went on, these two went from liking each other to hating each other to semi-loving each other. In the end, Greg went off to school and didn't come back until the fourth (and last) season. As great of a guy as Greg is and how good these two could have been, her intentions with this relationship were never pure.

Nathaniel Plimpton II

If there was one guy in the entire series that Rebecca should have ended up with, it would have been Nathaniel. This relationship transformed both people. Nathaniel became a softer, more vulnerable person because of Rebecca; conversely, Rebecca learned to be more honest and thoughtful.

All the mistakes Rebecca made with Josh, she learned from them with Nathaniel. Due to Rebecca trying to save Nathaniel's life, her honesty about her past came out and guess what? Nathaniel wasn't disturbed. Through the ups and downs, he loved Rebecca and wanted to help her.

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