Prison Break: 15 Sweetest Michael & Sara Moments

Michael and Sara’s Prison Break relationship was one of the most heartwarming aspects of the crime series. Though the series was an intense ride from beginning to end, filled with tough characters and shocking deaths, Michael and Sara delivered some of the most memorable moments that showed a real connection. A convicted felon and a prison doctor falling in love with each other made for an exciting setup, but that was just the beginning.

From the walls of Fox River to the Ogygia prison, Michael and Sara’s love had to overcome a lot of difficulties. Over time, both individuals have been loving and loyal to each other even when things have not gone according to plan. With moments of betrayal, reunions, and even a couple of fake-out deaths, it was a wild ride that made for an epic romance. Looking back on Prison Break, some of the most memorable moments are those that highlight Michael and Sara’s relationship.

15 Michael Gives A Flower For Sara’s Birthday

Michael’s Simple Gift Gets Through To Sara

It is likely that, as the prison doctor, Sara is used to getting attention from the prisoners she interacts with. However, something that likely sets Michael apart from them is that he is interested in her as a person and tries to get to know her on a personal level. During one episode, Michael notices flowers in Sara’s office and learns that it is her birthday.

However, Sara is not too keen on the flowers as a present (which came from her father) as she simply sees them as something that will wilt and die before long. After a conversation about cynicism versus optimism, Michael leaves behind an origami flower for Sara as a sweet birthday present. Not only is it a nice moment of him gifting her with something on her birthday, but it also speaks to the relationship they have. Unlike the real flowers that have a limited lifespan, Michael gifts her with something that will last.

14 Sara Tends To Michael’s Injury

Michael Reacts To Sara’s Compassion

Though Michael arrives in prison in Prison Break season 1 with a solid plan in place, that doesn’t always protect him from the other prisoners. One of the keys to his plan is convincing mobster John Abruzzi to help him in exchange for the identity of a rat in his organization. However, John isn’t one to negotiate and he attempts to torture the information out of Michael by cutting off his toe.

Sara is clearly a doctor who cares a lot about her patients, even if they are criminals. Seeing Michael hurt in this way draws compassion from her and she tries to get him to tell her what happened. Instead of making up some story that he knows she is not going to believe, he tells her “Don’t make me lie to you.” It shows a level of respect he has for her but also a relationship that he doesn’t want to tarnish.

13 Michael Tells Sara About His Fears

Michael’s Vulnerability Brings Them Closer

Michael is a bold man with this plan that he has in place. He is also tough, but that toughness is put to the test with the dangerous elements he is forced to live among in prison. He understands enough about prison to know that he has to maintain a persona of strength around the other inmates, but he allows himself to let his guard down around Sara and show some of the fear he has.

Following his attack from Abruzzi, Michael tells Sara about when he and Lincoln were younger and Michael was afraid of monsters in the dark. It is a charming story that highlights the close bond the Burrows brothers have and explains why Michael is so willing to risk everything in order to save his brother. However, it is also a moment of vulnerability where Michael opens up to Sara to let her see that he trusts her.

12 Michael Makes A Bet With Sara

Michael Imagines A Life For Him And Sara

It seems that throughout Prison Break, Michael and Sara are able to steal these little intimate and touching moments amid all of the chaos of the world they are in. This is even true in the first season of the show, where they can have these charming conversations together in her office, but the violence of their reality does often intrude. The more times Michael shows up in Sara’s office with a new injury, the more she worries about his safety.

In one instance, Sara ensures Michael that he is going to die if he does not take care of himself in prison. Michael attempts to address her concerns by making a bet with her that when he leaves prison alive, he will take her out to dinner. While she is not amused by his seemingly careless attitude in the face of death, it shows that Michael is thinking about a future in which he is no longer locked up, and they can have the relationship they both clearly want.

11 Michael Tells Sara His Plan

Michael Puts The Plan In Sara’s Hands

A lot of the tension in the first season of Prison Break comes from the anticipation of when Sara is going to find out about Michael’s plan. The closer the two become, the more it becomes clear that Sara will be devastated by the revelation. While there is no softening the blow of the truth, it comes in an unexpected way as Michael simply tells Sara the truth and asks for her help.

It is a tense moment with the two becoming combative with the impact of Michael’s confession, but there is no denying that this shows an incredible level of trust that Michael has for Sara. Instead of manipulating her and continuing to lie to her, he puts his entire plan at risk based solely on the fact that he thinks she is a good person and will do the right thing to help an innocent man.

10 Michael And Sara’s First Meeting

Sara And Michael Find A Quick Connection

When looking at Michael and Sara’s relationship, the first time they meet at the beginning of the Prison Break timeline is obviously an important moment for their future together. When getting to know each other, Michael asks why someone like Sara, being the governor’s daughter and all, would choose to work in a prison. She states that she believes in being part of the solution. Michael then quotes the famous Gandhi quote “Be the change you wish to see in the world”, which gets Sara’s attention.

It makes for a charming scene in a show that doesn’t feel like it will have too many of them. Within the dangerous walls of the prison, Michael is able to find someone he can connect to in a way that reminds him of his life on the outside. Given that he is in prison for honorable reasons in his mind, he is happy to meet someone decent. Likewise, Sara does not expect to meet an intelligent, polite, and considerate prisoner like Michael.

9 When Sara Looked Out For Michael in Fox River

Michael Found A Kind Friend In Sara

When Sara finds out that Michael and Lincoln are brothers, she suddenly feels a sense of empathy for Michael and extends him a listening ear in the prison. Not only does she provide Michael with a sense of emotional support during his visits, but she is considerate enough to schedule Michael and Lincoln’s infirmary visits close to each other so the brothers catch a glimpse of one another in the prison.

This offers Michael kindness that he doesn’t find much of in prison. He is doing so much to help his brother that someone helping him out of the goodness of their heart is touching to him. Sara goes as far as looking into Michael’s past and when asked by fellow nurse Katie why she was doing so, she said that she felt like Michael was someone she could get through to.

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8 When Michael Rescued Sara

Michael Plays Hero During A Prison Riot

“Riots, Drills and The Devil” is one of the most exciting episodes of the series, coming early in Prison Break‘s excellent first season. The episode sees a riot breakout in Fox River prison which puts Michael and the other hero prisoners in danger. However, as a prison employee, Sara also finds herself in a vulnerable place. Knowing this, Michael sets out in the middle of the chaos to find Sara and make sure she is okay.

Though Sara is able to defend herself well, when her office is beginning to be overrun, Michael arrives to pull her to safety. He then stays with her to ensure she makes it out of the ordeal safely. Michael not only puts himself in danger by rescuing Sara but also risks jeopardizing his breakout plans to save the good doctor. His heroics show her that he is not just a polite inmate but a good person.

7 Michael And Sara’s Many Reunions In Season 2

Tense And Romantic Reunions Further Their Romance

Sara and Michael’s relationship was at a standstill at the beginning of season 2. Following Michael’s escape, both parties found it difficult to not only unite but also mend their relationship. However, that didn’t stop them from trying to reconnect multiple times throughout the season. In season 2, episode 10, “Rendezvous”, they meet for the first time since the breakout, and Michael takes the chance to apologize to Sara for all the harm he had caused her.

Although this does not mend their relationship, it is obvious that they both still care for each other. They eventually meet up again in season 2, episode 16, “Chicago”, and this time Sara gives Michael a warm embrace and this is where they kiss for the first time outside the prison walls. By their final reunion in the finale episode of season 2, it becomes clear how much these two have fought to be together when they have a triumphant embrace.

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6 When Michael Finds Out Sara is Alive

Michael And Sara Reunite After A Fakeout Death

The reunion in the season 2 finale of Prison Break was an epic one, but it would be the last time these two characters saw each other for some time. Despite being a central part of the series from the beginning, actor Sarah Wayne Callies wasn’t in Prison Break season 3 as the showrunners decided to kill off Sara Tancredi. After being kidnapped by the Company, Lincoln is sent a decapitated head which is supposedly Sara’s as a warning.

However, as a result of fan outcry, the show brought her back at the beginning of season 4. It is revealed that the death was faked and Sara escaped to Chicago. After Michael and Lincoln are bailed out of prison by an associate who has been helping Sara, she and Michael are reunited once again. It is a moment of complete disbelief and relief on Michael’s part while also undoing one of the most controversial storylines in the show.

5 When Sara Calls Herself Michael’s Wife

A Small Lie Hints At Their Future

Given all the stress that Michael goes through over the course of the series, it is not surprising that it eventually catches up with him. When Michael collapses and finds himself in hospital in season, Sara stays patiently by his side while the doctors treat him. Afterward, Sara lets Michael know that in order to keep updated on his condition, she had to tell the nurses that she was his wife. Michael, pleasantly surprised, says “That has a nice ring to it”.

With Michael and Sara constantly on the run for their lives, it is not too often that these two have the time to share little moments where they can laugh together and even think about their future. This sweet moment is what keeps both parties fighting for each other during this season, especially as Michael’s condition deteriorates.

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4 Michael And Sara Finally Made Their Relationship Official

They Agree They Want A Future Together

Michael and Sara have had many ups and downs, to say the least. This has led to their relationship status being left up in the air. When they reunite in season 4, episode 2, Sara tells Michael that the only reason she stayed alive through Gretchen’s torture in season 3 was in the hopes that she could him again. Sara states that she wants a clean slate and for them to start fresh in their relationship.

Although Michael jokingly states that he hasn’t quite found the time to divorce his wife Nika and commit to Sara, he agrees that they both should put the past behind them and start fresh. In that episode, they finally decide to commit to one another and become a couple. After seeing them kept apart for so long and dealing with some of the mistrust of their previous time together, this was a triumphant moment of the two finally admitting to each other that they were each other’s endgame.

3 Michael And Sara Get Married

Michael And Sara Earn A Moment Of Happiness

Michael and Sara’s love for each other grows more and more apparent throughout the series with every new threat they face. Part of this is because, no matter what they are running from or dealing with, they always take the time to remind themselves that they love each other and this relationship is important to them. This eventually leads to them getting married in Prison Break’s two-episode movie.

Unlike Michael’s plans, which always seemed too elaborate and grandiose, Michael and Sara’s wedding was simple and minimal. Married at a beach with Lincoln and Sucre as witnesses and a marriage celebrant, this wedding was the sweetest break that these two characters ultimately deserved. Regardless of what they have been through and the difficult road that lies ahead, Michael and Sara seem to forget all of that and share this moment together where they are genuinely happy.

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2 Michael And Sara Reunite In Season 5

The Couple Overcomes Another False Death

Just as Sara had to supposedly die in the course of their relationship. The original run of the series ended with Michael’s apparent Prison Break death. It was certainly a tragic way to end the series given everything he and Sara had been through to be free and together, so it is not surprising that they walked back on this death as well.

Sara discovers that Michael is alive and being held prisoner once again in the Prison Break revival series, which serves as season 5. After years of not seeing each other, the two share an emotional reunion. Unlike their other reunions, this is not a passionate embrace but rather a tearful moment of years of injustice and pain keeping them apart, as well as tears of joy at finally being together again. Happily, they are able to enjoy the rest of their lives together along with their son, who Michael finally gets to meet.

1 Michael And Sara’s First Kiss

Michael And Sara Admit Their Feelings

First kisses on TV often make for some iconic romantic moments. There is usually a good build-up within these relationships, making the inevitable moment all the more satisfying for audiences. Michael and Sara are a great example of this, with their taboo and complicated romance throughout the first season building to a thrilling and deeply romantic moment they share together.

Even though Michael was using Sara as part of his escape, this first kiss showed that Sara wasn’t just part of the plan for Michael, as he truly started to fall for her and she for him. It was a long-awaited acknowledgment of the feelings that were obvious between them but that neither wanted to address. Although they don’t kiss again until Prison Break season 2, Michael and Sara’s first kiss is enough to keep viewers invested in their relationship until the next season.

Prison Break

Prison Break tells the story of two brothers who must unravel a political conspiracy while escaping from one of the most secure places on Earth. When petty criminal Lincoln Burrows (Dominic Purcell) is falsely convicted of murdering the Vice President’s brother, his own brother, Michael Scofield (Wentworth Miller), has himself incarcerated in order to stage a daring prison break using the blueprints of the facility he has tattooed on his body.  

Cast

Curtis Lum , Sarah Wayne Callies , Marina Benedict , Amin El Gamal , Wentworth Miller , Steve Mouzakis , Dominic Purcell , Bobby Naderi , Christian Michael Cooper

Release Date

August 29, 2005

Seasons

5

Writers

Paul Scheuring , Nick Santora