Timeless: 10 Most Heartbreaking Scenes, Ranked

When a show like Timeless involves trips to the past and a secret organization, fans know to expect the twists and turns. What they might not be ready to expect is just all the heartbreak that can come with those twists. The short-lived Timeless excelled at presenting fans with unexpected reveals while still tugging at those heartstrings.

The fan-favorite Time Team is put through the wringer in the series. Just as they solve one problem, a tragedy gets in their way. From lying families to deaths, Timeless has a way to break every fans’ heart.

10 Lucy Learns Her Mother Is Rittenhouse

Most fans were introduced to Timeless with the idea that it was about a trio preventing one villain from making changes to history as the TV show traveled through time. Pretty early on, however, the series introduced the mysterious Rittenhouse organization, and the actual villain of the series.

Lucy learns a lot about the group throughout the first season, and eventually, the stress of everything became so overwhelming to her that she starts to unload her confidential information on her mother. That proves to be a mistake as she discovers her mother, like her father, is a Rittenhouse legacy. Raised in the organization, Lucy’s mother is all about seeing their plan come to pass. Lucy’s entire world had already been turned upside down so much, but the moment her mother reveals the truth to her is particularly heartbreaking.

9 Wyatt’s Actions Don’t Save His Wife

When Wyatt learns that they’re preserving history, he’s on board with the mission. The soldier, also, however, defies orders because the idea of using a time-traveling vessel to prevent his wife from being murdered is too tempting.

He gets Rufus to help him as they travel to the 1980s to prevent the man who confessed to killing his wife from ever being born. Wyatt’s plan is simply to keep his parents apart. The plan goes sideways as Wyatt’s obsession takes over and he accidentally gets the father of the man killed. Unfortunately, when he returns to the present, Wyatt’s actions mean nothing to the timeline because his wife is still dead.

8 Jessica Returns

When Jessica Logan does return to the land of the living, it’s not a result of Wyatt’s meddling in the timeline. Instead, it’s Rittenhouse that’s responsible, but he doesn’t know that right away. All he knows is that the person he’s been grieving for years is finally alive.

The trouble is, this breaks the hearts of the audience because Jessica’s return comes right on the heels of Wyatt moving on with his life – with Lucy. The duo admit how they feel about one another on a mission, only for them to return to the present and Wyatt decides to give his relationship with Jessica a chance. It’s great to see Jessica make trouble on the show, but not so great for the audience to see Wyatt and Lucy forced apart.

7 Bonnie Parker Dies

American history buffs watching Timeless would have already known that Bonnie Parker and Clyde Barrow didn’t get a happy ending. The two notorious bank robbers went out in a blaze of gunfire. That’s the case for the show too, but the sequence is made all the more heartbreaking because the audience gets to know them through Lucy and Wyatt.

When Lucy and Wyatt cross paths with the two, they have to figure out why Rittenhouse is trying to get close to them. They pretend to be bank robbers as well, and Bonnie and Clyde invite them to stay with them. With Lucy and Wyatt pretending to be a couple, the criminal duo spill secrets and talk about their life together – as well as their dreams for the future. It makes Bonnie’s final moments all the more tragic as she refuses to back down from authorities.

6 Conner Thinks Fanboys Don’t Save The World

Rufus freely admits that his boss was once his hero in the world of science and technology. By the time the audience meets Conner, however, he’s been backed into a corner by Rittenhouse, and no longer willing to be an independent thinker.

When Conner goes on a mission alongside Rufus to the past, Rufus confronts him, and Rufus gets the response of, “fanboys don’t save the world,” from his former mentor. Not only is it sad that all of Conner’s excitement for the field he loves is gone, but also that he believes he can convince Rufus to give up the fight.

5 Denise Gives Lucy A Flash Drive

As the time team discovers early on, only the people actually traveling through time are aware when history is changed. Entire family trees can be wiped from existence by someone interfering in a moment in history.

When Denise realizes the gravity of this, she invites Lucy to dinner with her family. As Lucy’s boss, Denise hasn’t really opened up about her family up to that point in the show. Following dinner though, she gives Lucy a flash drive that contains photos and mementos of her family on it. She wants Lucy to carry it with her on missions in case anything ever happens that makes her forget that she ever had a wife and kids. It’s a horrible risk in their line of work, but at least Denise has the chance to realize she can try to preserve what she has.

4 Wyatt Is Prepared To Die At The Alamo

The standoff at the Alamo is a landmark historic event, and the time team ends up trapped there with seemingly no way to course-correct after Garcia Flynn changes history. It falls to Lucy to rewrite a letter that makes history, but it falls to Wyatt to protect them all.

Throughout the episode, Wyatt has flashbacks to his own time as a soldier, to a particular event that haunts him. His willingness to sacrifice himself to keep Lucy and Wyatt safe becomes an issue as he gives them orders that would see him staying behind while they escape. Lucy won’t accept that, and it’s one of the earliest emotional sequences in the series.

3 Jiya’s Vision Comes True

The season two final almost ended up being the series finale, which would have left a lot of fans heartbroken, indeed. In one of the highest-rated Timeless episodes (by both critics and fans), Jiya’s vision of Rufus being killed finally came true.

While that’s heartbreaking in and of itself, Jiya’s reaction is so much worse. She points all of her grief and anger at Connor when she returns to the present, berating him for allowing Rufus to come on a mission to save her when she warned them of the vision of his death. When she cries about there being no one there to claim Rufus’ body, the audience cries with her.

2 Flynn Sacrifices Himself

As is true for a lot of time travel movies and television series, the events of the plot have to come full circle to make sure the story gets started in the first place. While that’s true as Lucy passes her journal off to Flynn, putting the entire time-traveling journey in motion, before that, Flynn makes a huge sacrifice.

Flynn decides to give up his own life to make sure that Lucy is able to bring an end to Rittenhouse once and for all. It’s a tragic end for the antihero character, and certainly not the ending a lot of fans wanted for him, but it served to tie up the final story in the two-hour movie the show closed its journey with.

1 Lucy Learns Her Sister Doesn’t Exist

While Timeless features a lot of shocking moments, and deaths of beloved characters, the most heartbreaking of all might be the first heartbreaking moment in Lucy’s time on the show. In the pilot episode, Lucy gets asked to help on a secret project because of her historical knowledge. She says goodbye to her mother and her sister and goes to work. When she returns after her first trek through time, she no longer has a sister. It’s a shockingly tragic demonstration of what one change in the past can do to the present.

Lucy repeatedly asks about her, dreams about her, even makes a deal with Denise that she has to find a way to get her sister back. While Denise agrees to try, Lucy never does.

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