Ranking ‘Outlander’s 16 Most Heartbreaking Moments

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Fans of Outlander are no strangers to heartbreak. Whether it be for a happy occasion or a sad situation, the Starz series has been one big rollercoaster ride.

Since Outlander debuted in 2014, viewers have followed the turbulent love story of Jamie (Sam Heughan) and Claire (Caitriona Balfe) through 200 years in time. Nothing is ever easy and there have been plenty of tears shed along the way.

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Below, we’re taking a look at some of the show’s most heartbreaking moments. See where they rank from least to most heartbreaking.

Outlander, Season 6, TBA, Starz

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OUTLANDER heartbreaking ranked frank brianna
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16. Bree Sees Frank in Scotland (Season 4, Episode 7)

When Brianna travels through the stones to the 18th century, she begins her journey to America. But before boarding her ship, she looks back at the docks to see a vision of Frank smiling in approval. The bittersweet exchange gave Bree the assurance she needs to pursue her mother and biological father across the pond and surely brought a few tears to most fans’ eyes.

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15. Lord John Grey’s Confession (Season 4, Episode 6)

In Season 4 during an excursion to Fraser’s Ridge, Lord John Grey falls ill and Claire takes care of him while Jamie and Willie stay away for contagion reasons. While in his feverish state, John Grey admits to Claire that he’s in love with Jamie and envies her for her relationship with him. Claire reminds Lord John that he has Jamie’s son, so he’ll always have a piece of him — even if it’s not in the way he wishes.

Outlander Season 4 2018
Starz

14. Roger’s a No-Show (Season 4, Epsiode 13)

After months of traveling to track down Roger, Claire and Jamie return without him and new mother Brianna is devastated thinking he chose against being with her. Despite her parents’ reassurance that they will support her, Bree’s reaction to his absence is wrenching.

Outlander Season 4 2018
Starz

13. Ian Stays With the Mohawk (Season 4, Episode 13)

Upon their arrival in the Mohawk settlement in the Season 4 finale, the Frasers quickly learn they’ll need to come up with a plan to free the captive Roger. Ian decides to sacrifice himself, telling his uncle that he’ll remain with the natives in exchange for Roger’s freedom. Their tearful goodbye is filled to the brim with emotion.

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12. Frank’s Death (Season 3, Episode 3)

No matter what viewers think about Claire’s first husband, there is no denying that Frank tries his best to be a good father to Bree. So the shocking reveal that he passes away in a car accident makes his goodbye a bittersweet one. He may not be perfect, but his life isn’t exactly what he bargained for and he makes the best of it that he can.

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11. Bonnet’s First Attack (Season 4, Episode 1)

In the Season 4 premiere, the evil pirate Stephen Bonnet appears kindly on the outside but quickly turns on Claire and Jamie after they extend kindness his way. Robbing their boat, Bonnet’s worst offense — other than killing innocent crew members — is brutally ripping Claire’s wedding rings from her mouth after she tries to swallow them. She manages to retain her ring from Frank, but Jamie’s ring gets snatched from her.

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10. Claire Says Goodbye to Bree (Season 3, Episode 5)

Before Brianna joins her parents in the 18th century, Claire leaves her daughter in 1968 to go find her love in the past. Their emotional exchange is heightened with the understanding that they believe this is the last time they’ll ever see each other.

Outlander Season 5
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9. Jamie Says Goodbye to Murtagh (Season 5, Episode 7)

It’s never easy saying goodbye to beloved characters, especially when they’re as beloved as Murtagh Fitzgibbons. In Season 5, Jamie and Murtagh were on opposing sides in the battle at Alamance creek but the barriers fell once the elder fell victim to gunfire. As Jamie tended to his side, it was hard to not sob. Adding insult to injury, Jamie was wearing a red coat as the drama unfolded.

Outlander
Starz

8. Roger Struggles to Find His Voice (Season 5, Episode 8)

In a painful exploration of post-traumatic stress, Roger struggles to find his voice after being hung at the Alamance battlefield in Season 5. Between struggling to be the father and husband he used to be and working on his own mental health, Roger is saddled with a nearly impossible feat to overcome an extraordinary circumstance. As Roger’s struggles are depicted, it’s hard not to feel saddened for the historian.

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7. Jamie’s Trauma (Season 1, Episode 16)

After his imprisonment, torture and rape by Jack Randall, Jamie is dealing with the aftermath as he grapples with PTSD. In spite of Claire’s best efforts to understand, Jamie can’t look at her and it’s hard to see the tough highlander struggle.

Outlander Season 4 2018
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6. Brianna Meets Jamie (Season 4, Episode 9)

Not necessarily sad but definitely moving, the meeting between father and daughter brings them both to tears with the realization that they’re in the same place and time. And considering the fan fervor and anticipation for this scene, it’s certainly one of the best.

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5. Bree’s Assault (Season 4, Episode 8)

In one of the most brutal moments of the series, Bonnet rapes Bree after she approaches him about her mother’s ring she recognizes among his belongings. The assault also occurs moments after she and Roger part in anger leaving her feeling alone and viewers’ stomachs churning.

Outlander Season 5
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4. Jamie Finds Claire (Season 5, Episode 12)

The entire episode entitled “Never My Love” is traumatic, as Claire endures abuse and assault at the hands of Lionel Brown (Ned Dennehy). But when Jamie finally arrives at Claire’s side after massacring the group who held her captive, he sees how broken she is and it’s shattering.

OUTLANDER heartbreaking ranked
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3. Jamie Leaves Willie at Helwater (Season 3, Episode 4)

During Jamie’s time at the Dunsany family estate Helwater, he fathers Willie and despite not being able to claim him as his own, he gets a chance to spend quality moments with his own child. But eventually Jamie has to leave for fear people may see the resemblance between the two, so he departs with the promise that Lord John Grey will take care of him. Jamie’s pained expression as he rides away will have you reaching for tissues.

Outlander Season 2 2016
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2. Faith (Season 2, Episode 7)

Much of the Season 2 storyline involved Claire’s pregnancy with her and Jamie’s first child. But when she loses the baby — a daughter they name Faith — she blames his fight with Jack Randall which put her into premature labor. After Jamie is able to return home, Claire admits that she hated him for it and it’s enough to bring any viewer to tears.

Outlander Season 2 2016
Starz

1. Jamie Makes Claire Return to the Future (Season 2, Episode 13)

Since Jamie and Claire’s love story is the central aspect of this captivating series, the Season 2 finale scene between the husband and wife has to be the show’s most heartbreaking. Insistent that Claire returns to her own time so she and their unborn child can survive, Jamie tells her to go on without him as he prepares for the Battle of Culloden. Their whispered promises and steeling glances are both crushing and iconic.