Top 10 Most Heartbreaking Pretty Little Liars Moments

Haleb is one of "Pretty Little Liars'" four main pairings, and the show tries every trick in the book to break the couple apart. Hanna and Caleb call it quits four separate times, but the last one hurt the most. While the other breakups were a byproduct of all the crap that goes down in Rosewood, Haleb's Season 6 split was a result of the couple drifting apart over a five-year period. With Hanna's profession necessitating a lot of traveling, the fashion designer struggled to find time for Caleb, who grew sick and tired of playing second-fiddle to a job.

Charlotte may be a mentally unstable sociopath who manipulates the Liars like dolls in a playhouse, but the character's backstory genuinely tugs at the heartstrings. Foreshadowed in a number of short videos, Charlotte was born as Charles, a young boy who transitioned into a transgender girl. Unfortunately, Charles' gender identity proved to be a sticking point for the kid's adoptive father, who misread an act of kindness as an attempt to hurt Alison and institutionalized Charlotte in a psychiatric hospital. Punished for trying to be herself, Charlotte barely had a fighting chance.

Season 5's second half sees Alison standing trial for Mona and Bethany Young's murders, while the Liars attempt to prove the girl's innocence. Due to Alison's vindictive and cruel nature, particularly whenever Mona happens to be involved, the jury finds Ali guilty of murder in the first degree. As the icing on the cake, the verdict prompts Tanner to arrest Spencer, Emily, and Aria as accomplices. With most of the Liars in tears and behind bars, it truly seems like "A" has won the game.

The show literally has "liars" in the title, so trust issues are going to be a factor! Right from the start, these two girls clearly have feelings for each other, but Paige's reluctance to come out of the closet puts the brakes on any potential romance. Eventually, the stars align and Paily is born, but Alison's return puts a strain on Paige and Emily's relationship. Along with being Emily's first love, Alison bullied Paige, who finally takes revenge by informing the cops about Ali's whereabouts. No longer able to trust Paige, Emily says goodbye.

What is a teen drama without a love triangle? During those brief moments when "A" is not the focus, "Pretty Little Liars" tends to revolve around couples getting together, breaking up, or making up. After Caleb comes clean about still being hung up on Hanna, Spencer questions whether their relationship has a future. In an attempt to put things right, Caleb goes to Spencer's house to deliver an incredibly moving declaration of love. Unbeknownst to Caleb, at that very moment, Hanna happened to be staying at Spencer's place. By the end, there was not a dry eye in sight!

The Liars are pros at keeping secrets, but certain truths are too significant to hide. "Pretty Little Liars" handles Emily's sexual awakening in a sensitive and realistic manner, as the teenager gradually realizes this is more than just an experimental phase. Tired of pretending to be someone else, Emily comes out to her father in a scene that is simultaneously cathartic and nail-bitingly intense. Emily's mother reacts rather poorly to the news, but both adults eventually came around to accept the high school student's sexuality.

From the pilot to the finale, Aria and Ezra's turbulent relationship lasts the distance, but one moment threatened to derail everything. In a single episode, Aria learns that Ezra is a liar, a true mystery writer, and may potentially be "A." Aria discovers a manuscript Ezra has been writing about Alison's supposed murder, containing details about Aria and the other Liars. Ezra's explanation only makes things worse, leading to a harrowing scene were a devastated Aria breaks up with Ezra. Just in case Lucy Hale's brilliant acting failed to sell the moment, the breakup happens on a ski lift.

Manipulative and resentful, this teenage bully is not always the most likable person in Rosewood, but a near-death experience tends to change one's personality. Initially assumed to have been murdered, Alison resurrects from the dead to reveal what truly happened that night. After returning home, Alison was attacked and seemingly killed by an unknown assailant. Rather than run to the cops, Alison's mother elected to protect the would-be murderer by burying the corpse. Temporarily paralyzed due to the attack, Alison could only watch as Jessica covered up the crime.

During Season 3, "Pretty Little Liars" exposes Toby as the new "A," a revelation that shocks nobody more than Spencer. On the relationship’s one-year anniversary, Spencer confronts and smacks the hell out of Toby, but the real gut-punch occurs after the couple officially split. Desperate for some closure, Spencer storms Toby's door and demands answers, before ultimately breaking down into a sobbing mess. Adding insult to injury, the only person inside Toby's place is the amused Mona, who gleefully eats the couple's anniversary dinner while Spencer cries in the background.

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

Spencer & Toby Break Up
"Over My Dead Body"

Caleb Goes to California
"Picture This"

Emily Loves Alison
"The Perfect Storm"

Spencer Believes Toby Is Dead
"Will the Circle Be Unbroken?"

Mona’s Dollhouse Breakdown
“Game on, Charles"

"Pretty Little Liars" seldom hesitates to ax or revive a character, but there was no coming back from one specific death. Declared missing a few episodes prior, Maya's history with drug addiction suggested the girl had simply run away; unfortunately, that was not the case. Out of nowhere, the Liars learn that the police have found Maya's dead body, and the cast's distressed reactions are absolutely heartbreaking. Along with supplying one of the show's best twists, Maya's death served as a reminder that "A" was not the only person worth fearing.