We are he has narrated many relationships over the past five seasons. From the iconic fairytale romance between Jack and Rebecca, Randall and Beth’s healthy and inspiring marriage, and Kate and Toby’s adorable relationship that has evolved since the first episode, We are knows how to tell a good love story.
Most of Kevin Pearson’s journey through the years has been the search for his great love story. He went back to his first love, built long-term relationships that ultimately failed, but never gave up. The fans have done their bit as to who his true love and future wife will be, but only time and creator Dan Fogelman will tell what it’s supposed to be and when.
7 Olivia
Kevin’s brief affair with his co-star Olivia Maine was a cute story of enemies for lovers, but it was also just that; ephemeral. Kevin and Olivia were going to star in the play together, The back of an egg but Olivia’s fickle and authoritative attitude led her to ditch Kevin and the project entirely.
The only thing Olivia and Kevin really had in common was that they were both actors. He tried to make their relationship more serious by taking her home for Thanksgiving, but that only made things more awkward and proved they would never last long.
6 Sloane
Sloane wrote The back of an egg and it was the antithesis of its star, Olivia. When Olivia left the network, Sloane became the star of her own production and developed a relationship with her lead actor, Kevin. The two were an unlikely match and far 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 before. Their relationship never had a chance to develop, and because of that, it was ultimately not very credible. That, and after a deep conversation with Toby, it was revealed that he was still hung on his first love.
5 Cassidy
The season 4 premiere featured war veteran Cassidy Sharp, a recovering alcoholic who befriends Kevin and his uncle Nicky. She and Kevin are off to a rocky start because she isn’t impressed with his big ego and superstar status. However, he allows her to realize that she wants to save her failed marriage and her estranged relationship with her young son.
Cassidy and Kevin break up have a brief romantic relationship That ends quite abruptly once Cassidy decides that it belongs to her ex-husband, Ryan, and she needs to work harder to repair what she broke. The chemistry between Kevin and Cassidy was strong enough to lay the foundation for a lasting relationship, yet the characters were in two different places in their lives, and it ultimately didn’t work out.
4 Adult sophie
Sophie and Kevin’s childhood love story is one of the books, so it’s no wonder fans continue to support them even after seeing them break up multiple times. Unfortunately, his relationship with Sophie as an adult never seems to work.
Professing their love after not seeing her for 12 years in Season 1, the two decide to try their relationship again, this time in their 30s. Kevin’s alcoholism and recognition of the disappearance of their marriage (Kevin cheated on her) leads them to break one more time. 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 their father’s war experience. Their relationship was, for a long time, the strongest Kevin had had since Sophie. They communicated well together and she tried to help him combat 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 children. They try to make it work for a while, but Zoe makes it clear to Kevin that he’s not going to back down in front of the kids and that he knows he needs to be a father, so she lets him go. It’s a heartbreaking breakup, but a relationship Kevin needed to help him grow.
two Teen Sophie
What began as a childhood crush on his sister’s best friend Kate led to decades of The princess Bride Y Goodwill hunting references. Kevin and Sophie remained madly in love from when they were children to their early 20s. They went to prom, moved to New York together, and got married.
Sophie was on par with Kevin the night Jack died, and she was by his side throughout. It’s a shame Kevin and Sophie didn’t work out in the long run, because their teenage relationship was reminiscent of the love Kevin wanted so badly later in life. Ultimately, this romance taught her to treat her future partners better and to never stop looking for love.
1 Madison
Madison has been present at all the great events in Pearson’s life. From being present at Kate and Toby’s cute reunion to planning their wedding and being there for the birth of their son, Madison has always been a true friend and someone the Pearsons 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 later led to her getting pregnant with her twins.
Madison and Kevin’s relationship is still slowly building, even after she gave birth to their children, Frances and Nicholas. They started the other way around, starting a family before falling in love. However, their romance has incredible potential to give both of them the love they deserve. Madison holds Kevin accountable and Kevin makes Madison more authentic. Kevin finally has the pieces to complete the puzzle of his perfect life, all he has to do is put the pieces together.
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