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10 Major Relationships, Ranked Least To Most Successful

Leonard Vanya Alison Raymond Hazel Agnes Umbrella Academy

Even though it’s only had two seasons, The Umbrella Academy has established itself as one of TV’s most unique superhero shows. It plays with time travel concepts in a fascinating way while focusing on the oftentimes dysfunctional family trying to save the world.

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In addition to the family dynamic, the show also explores the romantic relationships between the characters, most of which usually involve at least one of the Hargreaves children. In between trying to stop the apocalypse twice, the characters have had several important romances, varying from terrible to good, even though most were only temporary.

10 Ben and Jill

Ben and Jill The Umbrella Academy

Despite originally wanting to return to San Francisco after being transported with Klaus to 1963, Ben starts to have feelings for Jill, a member of Destiny’s Children, upon arriving in the past.

After a lot of begging, Ben convinces Klaus to let himself be possessed so that he can talk to Jill. The two end up spending most of the day together and end up kissing before being interrupted by Diego, who tells them of Five’s plan to return to the future. Unfortunately, because they leave the cult behind so abruptly, Ben never gets a chance to tell Jill who he really is before his death.

9 Diego and Patch

Patch and Diego The Umrella Academy

Eudora Patch is Diego’s partner at the police academy before he gets kicked out. Afterward, the two start a relationship that ends for an unknown reason. They begin to work together again when Patch, now a detective, catches Diego leaving an investigation at Griddy’s Doughnuts after it’s attacked. Ignoring her pleas for him to stay out of it, Diego continues to interfere with the investigation.

After the death of his mother, Diego goes to Patch and she comforts him, knowing how close the two were. Sadly, Patch is killed by Cha-Cha after finding Klaus, who had been kidnapped, and helping him escape before Diego arrives late to find her bleeding out. After mourning Patch, Diego begins to hunt down Cha-Cha and Hazel to avenge her death.

8 Vanya and Leonard

leonard and vanya woods

While things aren’t going great for Vanya at first, they start looking up after she meets her new violin student, Leonard Peabody. The two bond and eventually form a relationship with Vanya believing Leonard is the only one that understood her.

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She later discovers that he wants her to use her powers to hurt her family as revenge for being turned away from the Umbrella Academy when he was younger. After Leonard manipulates Vanya to hurt Allison, he tries to get Vanya to use her powers against the others but she refuses. When he lashes out at her in response, Vanya uses her powers to kill him.

7 Lila and Diego

The Umbrella Academy Diego and Lila

After arriving in Dallas in 1963 and attempting to stop the assassination of John F. Kennedy, Diego is put in a psychiatric hospital. There, he meets a fellow patient, Lila Pitts, who helps him escape when the Swedes come looking for him.

After making it out successfully, a relationship sparks between them but what Diego doesn’t learn until later is that Lila is actually the daughter of the Handler — and meant to keep tabs on him. Before he can leave 1963 with his family, Lila drugs him and attempts to get him a job at the Commission but he escapes. She eventually displays powers and reveals that she was one of the children born on the same day as the others. When Lila learns that the Handler killed her real parents, Diego lets her escape before admitting that he loves her.

6 Klaus and Dave

After accidentally time-traveling to the A Shau Valley in 1968 during the Vietnam War, Klaus meets a soldier named Dave Katz. Klaus joins the army alongside Dave and the two fall in love with each other. Unfortunately, Dave is shot in the back during battle and dies in Klaus’ arms from the gunshot wound.

After losing Dave, Klaus returns to the present and attempts sobriety in an effort to be able to conjure him. When Klaus and his siblings get sent back in time to 1960, he finds and attempts to keep a young Dave from enlisting in order to prevent his death, using his nametags from the future to try and convince him. However, due to Klaus’ interference in the timeline, Dave’s uncle enlists him in the Marines instead of the Army much earlier than before.

5 Luther and Allison

The Umbrella Academy Allison Luther

Although they are basically siblings, Luther and Allison share an obvious romantic connection with each other. The relationship started when they were younger when the two would sneak off to be alone together and while they go their separate ways, with Allison getting married and having a child, their feelings for each other resurface after they reconnect following the death of their father.

After being transported to 1962, Luther tries looking for her but doesn’t find her until years later. He becomes extremely distraught after learning that she had gotten married and moved on, leading him to intentionally let himself get hurt. However, there could still be a chance for them considering Allison is no longer married.

4 Reginald and Grace

Reginald and Grace The Umbrella Academy Season 2

While it’s unclear when they first met, Grace worked alongside Reginald on the mission to send Pogo into space.

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The two seemed pretty happy together but she decides to leave him after Diego makes her aware of Reginald’s secret plans involving the President, and Reginald refuses to tell her about them when confronted.

3 Sissy and Vanya

Umbrella Academy season 2 Sissy Harlan Vanya

When Vanya first lands in 1963, she almost immediately gets hit by a car driven by a woman named Sissy, causing her to get amnesia and have no memory of her life before. The family that hit her takes her in and she lives with them on their ranch where she forms a connection with their son, Harlan, and a bond with Sissy develops into a romantic relationship behind her husband, Carl’s, back.

After her family finds her, Vanya attempts to leave with Sissy and her son and return to 2019 but she ends up being caught by the police. She eventually manages to escape, but Sissy says she and Harlan can’t go with her on the off chance they get separated while returning.

2 Raymond and Allison

After being transported to 1961, Allison finds shelter in a Black-owned hair salon where she is given a job. She has been working there for months when she meets Raymond Chesnut, a member of the civil rights movement, who asks her on a date.

The pair eventually marries, she joins the civil rights movement herself, and they live a happy life together for some time before her siblings begin to show up. Raymond becomes afraid of Allison when she uses her powers to stop a cop from killing him but understands when she reveals the truth about her powers and her family. Unfortunately, Allison and Raymond’s relationship comes to an end when she has to return home without him, despite her offering to bring him along.

1 Hazel and Agnes

Agnes and Hazel The Umbrella Academy

Agnes Rofa worked at Griddy’s Doughnuts where Hazel, an assassin for the Commission, would frequently come in to get coffee. Eventually, Hazel and Agnes’ friendship develops into a romantic relationship and upon learning about Agnes’ dreams about owning her own bakery, Hazel decides to quit working for the Commission. As a result, Agnes is then taken hostage by Cha-Cha and then by the Handler herself, who wants them to complete their assignment. However, Hazel manages to stop both of them and free Agnes before asking her to run away with him. Despite finding out about his past, Agnes agrees and the two narrowly escape the Apocolypse using a briefcase.

In season 2, a much older Hazel arrives to give Number Five pieces of information about the assassination of John F. Kennedy, and he also reveals that he and Agnes were together for 20 years before she died of cancer.

NEXT: The Umbrella Academy: 10 Questions We Want Answered

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