This is Us has chronicled many relationships throughout the past five seasons. From the iconic fairytale romance between Jack and Rebecca, the healthy, inspiring marriage of Randall and Beth, and Kate and Toby’s adorable relationship that has evolved from the very first episode, This is Us knows how to tell a good love story.
Most of Kevin Pearson’s journey through the years has been his search for his great love story. He’s gone back to his first love, built long-term relationships that ultimately failed, but he never gave up. Fans have given their two cents as to who his true love and future wife will ultimately be, but only time and creator Dan Fogelman will tell what is meant to be and when.
7 Olivia
Kevin’s short-lived romance with his co-star Olivia Maine was a cute enemies to lovers story, but it was also just that; short-lived. Kevin and Olivia were set to star together in the play, The Back of an Egg but Olivia’s self-entitled, flighty attitude led her to ditch Kevin and the project completely.
The only thing Olivia and Kevin really had in common was that they were both actors. He attempted to make their relationship more serious by bringing her home for Thanksgiving, but that only made things more uncomfortable and proved that they were never going to last longterm.
6 Sloane
Sloane wrote The Back of an Egg and was the antithesis of its star, Olivia. When Olivia went off the grid, Sloane became the star of her own production and developed a relationship with her lead actor, Kevin. The two of them were an unlikely pair, and much more compatible than Olivia and Kevin.
However, Sloane and Kevin’s relationship was also incredibly short and seemed mostly like a rebound from the famous actress he dated prior. Their relationship was never given the chance to be fleshed out, and because of that it ultimately didn’t come off as very believable. That, and after a deep conversation with Toby, it was revealed that he was still hung up on his first love.
5 Cassidy
The Season 4 premiere introduced war veteran Cassidy Sharp, a recovering alcoholic who befriends both Kevin and his uncle Nicky. She and Kevin get off to a rocky start because she is unimpressed with his large ego and superstar status. However, he allows her to realize that she wants to save her failing marriage and estranged relationship with her young son.
Cassidy and Kevin end up having a brief romantic relationship that ends rather abruptly once Cassidy decides that she belongs with her ex-husband, Ryan, and needs to work harder to mend what she broke. The chemistry between Kevin and Cassidy was strong enough to build the foundation for a lasting relationship, however the characters were just at two different places in their lives, and ultimately didn’t work out.
4 Adult Sophie
Sophie and Kevin’s childhood love story is one for the books, so it’s no wonder fans continue to root for them even after watching them part ways several times. Unfortunately, his relationship with Sophie as an adult never seems to pan out.
Professing his love after not seeing her in 12 years in Season 1, the two decide to try their relationship again, this time in their 30’s. Kevin’s alcoholism and acknowledgment of the demise of their marriage (Kevin cheated on her) leads to them breaking up yet again. They reconnect on a friendly level throughout the series, but the episode “A Hell of a Week: Part 2” hints that their story has officially come to an end.
3 Zoe
Kevin and Beth’s cousin, Zoe, develop a relationship at the end of Season 2. Later, they travel to Vietnam together to learn more about his father’s war experience. Their relationship was, for a long time, the strongest Kevin had had since Sophie. They communicated together well, and she attempted to help him battle his alcoholism.
At one point they even move in together and start discussing their future. However, Kevin wants to be a father and Zoe has no interest in having kids. They try to make it work for a while, but Zoe makes it clear to Kevin that she is not going to budge on the kid-front, and that she knows he needs to be a dad, so she lets him go. It’s a heartbreaking breakup, but a relationship Kevin needed to help him grow.
2 Teen Sophie
What started as a childhood crush on his sister Kate’s best friend led to decades worth of The Princess Bride and Good Will Hunting references. Kevin and Sophie stayed madly in love from the time they were kids until their early 20’s. They went to prom, moved to New York together, and got married.
Sophie was even with Kevin the night that Jack died, and stood by his side through it all. It’s a shame that Kevin and Sophie didn’t work out long term, because their relationship as teenagers was reminiscent of the love Kevin so badly wished for later in life. Ultimately, this romance taught him to treat his future partners better, and to never stop looking for love.
1 Madison
Madison has been around for all of the Pearson’s big life events. From being present at Kate and Toby’s meet-cute to planning their wedding and being present for the birth of their son, Madison has always remained a true friend and someone the Pearson’s may have taken for granted. Kevin initially showed disdain for his sister’s friend, but eventually, they formed a connection that led to them sleeping together. This then led to her becoming pregnant with his twins.
Madison and Kevin’s relationship is still slowly building, even after she gave birth to their kids, Frances and Nicholas. They started backward, creating a family before falling in love. However, their romance has an incredible amount of potential to give them both the love they deserve. Madison holds Kevin accountable, and Kevin makes Madison more authentically herself. Kevin finally has the pieces to complete his perfect life puzzle, all he has to do is put the pieces together.
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