Top 10 Saddest Crazy Ex-Girlfriend Moments

We hope you have a box of tissues nearby. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Saddest Crazy Ex-Girlfriend Moments.

For this list, we’ll be looking at times in the show’s four seasons that brought tears to our eyes. Please note: this video will contain major spoilers.

#10: Rebecca Lashes out at Her Friends
“Josh’s Ex-Girlfriend Is Crazy”

When Rebecca’s past finally catches up with her and her friends, they all run to her side and attempt to help the only way they know how. Unfortunately, she feels ambushed and becomes defensive, lashing out and viciously targeting their insecurities. It breaks our hearts to see Rebecca spiral out of control but as hurtful as her comments are, we ultimately wind up feeling, above all else, sympathetic. The more she feels trapped, the crueler her comments become but it's still a clear cry for help. After she storms out we watch her continue to sink deeper into that dark place until she finally hits rock bottom.

#9: The Truth About Rebecca’s Dad
“Josh Has No Idea Where I Am!”

Rebecca always believed that her mom was the reason that she never got to see her dad growing up. But in a flashback to her childhood, she learns that isn’t quite the case. Young Rebecca is understandably super excited to spend time with her dad, which only makes it all the more heart-wrenching when it becomes painfully clear that the feeling isn’t mutual. The argument between Rebecca’s parents is tough to watch; her mom pleads with her dad to spend time with his daughter, but to no avail. Making this heavy dose of heartbreak even worse is the fact that Rebecca can’t recognize that her mother was acting out of love for her in this moment.

#8: Audra Has a Melt Down
“I Need to Find My Frenemy”

After Rebecca abandoned her seemingly perfect life in New York, frenemy Audra Levine felt she finally had the upperhand in their rivalry. When the pressures of being perfect get too hard, however, she abandons her family and moves to Vegas, taking a page out of Rebecca’s book. Rebecca tells Audra that she still struggles with her decisions on a daily basis, causing the former frenemies to finally confront reality. Audra is usually the character we love to hate but at this moment we can’t help but feel sorry for her.

#7: Nathaniel’s Mom
“Josh Is Irrelevant”

After Rebecca’s suicide attempt, Nathaniel wants to reach out but something is holding him back. A photo on his desk brings up a repressed memory from his childhood so he goes to confront his parents about it. At first they refuse to discuss the issue but eventually his mom realizes it’s time to be open and frank about the past. We defy you not to tear up when Nathaniel tells his mom he loves her and that he’s there for her - especially since he then finally finds the right words to say to Rebecca.

#6: Women in Prison Tell Their Stories
“I Want to Be Here”

Crazy Ex-Girlfriend never shies away from harsh realities or tough subject matter. While in prison, Rebecca urges her fellow inmates to use their stories to put on a musical. However, in stark contrast to the “Cell Block Tango”, from which this song takes inspiration, there’s nothing sexy about these women’s tales. Only Rebecca is committed to adding some razzle-dazzle to the song, while the other women provide “bleak anecdotes” that highlight the grim truth of the criminal justice system. By the end of the song, we’re feeling as deflated as Rebecca.

#5: Paula Has a Heart Attack
“I Need a Break”

This episode was praised for showing symptoms of heart disease normally not shown on TV or movies, and how they differ between women and men. As always, Paula is overworked with no signs of slowing down, even when she’s feeling under the weather. Mrs. Hernandez convinces her to visit the gynecologist to see if it’s the onset of menopause but sadly the diagnosis is far more dire. It’s hard not to get choked up when Paula tells Rebecca she doesn’t have time to be ill, but promises to take better care of herself.

#4: Valencia & Father Brah
“I’m Not the Person I Used to Be”

In the love story none of us saw coming, Valencia confesses to Heather than Father Brah is the one that got away. She always assumed that he simply didn’t love her the same way, until she discovers that he never actually received the letter that she wrote to him declaring her love. Sadly, it’s 12 years too late when he eventually gets her note, but the star-crossed lovers finally get some closure on what might have been. It’s bittersweet as they admit they’ve missed their chance to be together but they’re both happy with the way their lives turned out.

#3: Season Two Finale
“Can Josh Take a Leap of Faith?”

The episode is called “Can Josh Take a Leap of Faith?” and (spoiler) the answer it turns out is no. Rebecca thinks getting married will solve all her problems, so when she learns of her runaway groom she goes into meltdown. She ponders why every man she’s ever loved leaves her and blames herself for all her failed relationships, including the one with her father. While Paula assures her that this is not the case, it only ignites Rebecca’s fury and it’s devastatingly clear that she’s headed down a slippery slope.

#2: Dr. Akopian Tells Rebecca She Deserves Love
“Nathaniel and I Are Just Friends!”

When Nathaniel confesses his feelings to Rebecca, she’s afraid to reciprocate, based on her previous experiences. Dr. Akopian tries to reason with her that she’s not the person she used to be, but that brings little comfort. The therapist then proceeds to tell Rebecca that she deserves love, in a moment that’s likely to bring you to tears. And if that doesn’t do it... Rebecca’s answer definitely will. Dr. Akopian tells Rebecca that while she understands her fears, she hopes one day Rebecca will learn that she deserves love, and we couldn’t agree more.

Before we unveil our top pick, here are so honorable mentions.

Rebecca Comes Clean to Paula, Nathaniel & Josh
“Nathaniel Is Irrelevant”

Rebecca Asks Nathaniel to Let Her Be Happy
“I’m Almost Over You”

Rebecca’s Parents Break Up
“I Hope Josh Comes to My Party!”

“You Stupid...”
“That Text Was Not Meant for Josh!”

White Josh & Daryl Break Up
“Getting Over Jeff”

#1: Rebecca Overdoses
“I Never Want to See Josh Again”

Mental health is a major theme throughout the series and this episode brought Rebecca and the show to it’s darkest place. Feeling completely trapped and at a loss, Rebecca decides to overdose on her mom’s anti-anxiety medication. What breaks us is when Rebecca tells Paula that she didn’t want to die, she just wanted the pain to stop. It’s so hard to watch and we sincerely doubt that there was a single dry-eyed viewer when this episode aired. Thankfully, it ends with a message of hope as Rebecca decides to reach out and get help.