Because his wedding to Madison wasn't quite what he planned.
Going into the Season 5 finale of This Is Us, fans knew both Kevin and Madison were having cold feet. But even so, everyone was convinced the wedding would go forward. After all, viewers have known Kevin would eventually get married ever since they saw him sporting a wedding band in the Season 3 finale flash-forward to 2034. But it turns out that wedding didn’t happen in 2021, at least, not in this episode. So, who does Kevin marry on This Is Us — and more importantly, when does he finally tie the knot?
Warning: Spoilers for the This Is Us Season 5 finale follow. You have been warned. TBH, had fans not been so certain they knew how the future unfolds, Madison’s decision to not marry Kevin might not have felt like such a surprise. She was in love with Kevin, but Kevin, despite his hopes that his might develop feelings for the mother of his children down the line, was not in love with her. At least, not yet. Madison deserved better, and no one could argue that.
But that left fans in a tizzy. Kevin will get married, that much is certain. But to whom? Moreover, is he married in 2026? The flash-forward at the end of Season 5, Episode 16 was very careful not to show his left hand.
Let’s run down some theories:
It’s long-shot odds for Zoe, but let’s consider that it was she who first caught Kevin off guard about his true feelings for Madison. She knows Kevin better than he knows himself on some level. And they are both still in the same business. At least, they are for now.
When they were together. their big point of contention was she didn’t want children, and he did. That’s no longer a stumbling block. Kevin has kids, and they have a mother. Zoe can be a fun step-mother figure without getting pregnant, going through the infant phase, or even dealing with too much of the toddler stuff. For someone who likes kids, but doesn’t want to have them herself, it’s practically ideal.
Until Madison’s pregnancy, Cassidy was a fan-favorite to marry into the Pearson family. She was introduced in Season 4 as a character who would become very important in the Pearson story, alongside Malik and Jack Jr.
Jack Jr., obviously, is the next generation of Pearsons. And Malik has been both a main squeeze to Deja and a mentee to Randall. Cassidy, on the other hand, hasn’t had much to do. She slept with Kevin once, and since then, she’s had a few phone calls with Nicky. Viewers also noticed her marriage might have ended — in the scenes when she’s talking to Nicky, there’s no husband anywhere to be seen.
Some fans theorized she could be Nicky’s future wife, and that’s still a possibility. But if Madison is off the table for Kevin, then Cassidy could be back on.
But is Madison really off the table? Listen, she walked away from the altar today, but that doesn’t mean her relationship with Kevin is over. They still have kids together. Moreover, she openly admitted she’s in love with him. The problem was Kevin couldn’t find it in him to say it back. He hoped one day he would, but right now, he doesn’t love her in that way.
At least, not yet. Viewers couldn’t help but notice how great they seemed together in the 2026 flash-forward as she playfully tried to swat him out of Kate’s hotel room. Now, that could just be the two of them riding high on Kate’s happiness. It could be that they’ve found a place of friendship as co-parents of twins. But let’s never say never here.
It always comes back to Sophie. Kevin’s tried to make a run of it with his childhood sweetheart twice. He’s screwed it up both times. But the way he acted when she called him in Season 5’s penultimate episode had fans very concerned for his relationship with Madison, which he may now no longer have.
Note that Sophie changed her phone number, although she didn’t say why. Could her impending marriage have gone belly-up, necessitating such a change? Also, Kevin deleted her contact from his phone, lest he give in to temptation and call her back. If he were fully over Sophie, Kevin would have left her contact in there with no worries of what could happen.
Part of Kevin will never be over Sophie. And that’s why she’ll never be off this list.
Consider this: What if I told you at the mid-point of This Is Us Season 5 (so Episode 9, “The Ride,” which aired on Feb. 23) that in seven short episodes, the Season 5 finale would show Kate in a 2026 flash-forward almost definitely marrying Phillip.
You know what you’d say?
Who?
Phillip wasn’t even introduced into the series until Episode 12 of Season 5. Now, suddenly, here the show is, teasing that Kate is going to marry the man most people thought of as “that jerky guy with the British accent we’ve seen for exactly five minutes.”
My point is, time is weird. All fans know is that Kevin is married by 2034. That’s 13 years from now. A lot can happen.
