If you spent years watching the waves crash against the Maryland coast and wondering if Abby O’Brien would ever actually find "the one," you aren’t alone. For a long time, it felt like Trace Riley was the only possible answer. Their history was heavy, their chemistry was undeniable, and fans were deeply invested in that "hometown sweetheart" trope. But then Jesse Metcalfe left the show, and everything shifted.
By the time the series finale rolled around in 2022, the big question wasn't about Trace anymore. It was about whether the high-powered, eccentric billionaire Evan Kincaid could actually fit into the chaotic, cozy world of the O’Brien family. Honestly, the way it wrapped up was exactly the kind of "feel-good" moment Hallmark fans live for.
The Big Reveal: Who Does Abby End Up With on Chesapeake Shores?
Abby O’Brien ends up with Evan Kincaid.
It wasn't just a casual dating situation by the end, either. In the series finale, titled "All or Nothing at All," Evan goes big—which is pretty much his brand. He takes Abby to a stunning new house he bought on the Bay. He isn't just showing off real estate; he’s showing her a future. He tells her how happy he’s been since coming to Chesapeake Shores and how much he loves her and her entire family.
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Then, he drops to one knee. Abby says yes, they get engaged, and the show closes with them firmly established as a couple ready to blend their lives.
Why Evan and Not Jay?
Remember Jay Ross? The sweet teacher who seemed like the safe, stable choice? At the start of Season 6, the writers finally cleared up that cliffhanger voicemail from the Season 5 finale. While the show tried to make us think it could go either way, it turned out Abby called Evan.
Jay was a great guy, but let’s be real: the passion just wasn't there. Executive producer Phoef Sutton even mentioned in interviews that the plan was always to have Abby choose Evan because he was a more "exciting" and "interesting" match. He challenged her in ways Jay didn't. Plus, the banter between Meghan Ory and Robert Buckley (who played Evan) brought a fresh energy to the show that it desperately needed after the heavy drama of the Trace years.
The Journey from Business Partners to Life Partners
The transition from "eccentric client" to "fiancé" was a slow burn. When Evan first showed up, he was a billionaire who didn't really "do" family or roots. He lived in hotels and focused on his business empire. Abby was the grounding force he didn't know he needed.
One of the best parts of their relationship was how Evan integrated into the O’Brien clan. He didn't just love Abby; he loved the whole circus. Whether he was hanging out on the couch or navigating the family’s intense dynamics, he fit. By the finale, he even makes sure his new house has room for Abby’s daughters, Carrie and Caitlyn, and even Mandrake, his loyal assistant. It wasn't just a romantic proposal; it was a commitment to her entire world.
The Trace Riley Factor
We have to talk about Trace for a second because for many viewers, he was the "endgame" for years. When Trace left at the beginning of Season 5 to find himself (and his music), it left a massive hole.
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However, looking back, the Abby and Trace relationship was often exhausting. It was a cycle of "will they, won't they" and "I'm leaving, I'm staying." Evan provided something different: someone who actually showed up and wanted to build a permanent home in the same place she did.
What Happened to Everyone Else?
To understand why Abby’s ending felt so complete, you have to look at the atmosphere of that final episode. It was a massive celebration of the O’Brien family.
- Mick and Megan: They officially remarried in a beautiful ceremony at the B&B. It was the full-circle moment the show had been building toward since the pilot.
- Jess and David: They had their own bombshell—Jess is pregnant! After a season of worrying about David’s father and their future, this was the perfect "happily ever after" for them.
- Kevin and Sarah: They welcomed their baby, "Little Mick," bringing a new generation into the house.
- Bree and Luke: Despite some major hurdles and Luke’s tendency to run when things get tough, they ended the series committed to each other.
Why This Ending Worked for Abby
Abby started the series as a stressed-out Wall Street professional who had lost her way. She came home to find herself again. Ending up with Evan—a man who is successful but willing to "still his life" for her—symbolized that she finally found the balance she was looking for. She didn't have to choose between a career and a family; she got a partner who supported both.
The finale didn't just give her a ring; it gave her a partner who understood her responsibilities as the new President of O’Brien Construction (since Mick retired) and as a mother.
Actionable Insights for Fans:
- Rewatch the Pivot: If you want to see exactly where the tide turned, go back to Season 5, Episode 7 ("What's New?"). That's when the "eccentric billionaire" facade starts to crack and the real connection with Abby begins.
- Check Out the Cast's Other Work: If you miss the chemistry, Robert Buckley is a staple in the Hallmark world and One Tree Hill alum, while Meghan Ory has a great stint in Once Upon a Time.
- Look for the "Easter Eggs": In the finale, listen to the jazz music playing in Evan's new house. It’s a callback to his earlier conversations with Abby about his tastes and hers, showing just how much he was paying attention.
The story of Chesapeake Shores is ultimately about coming home. For Abby, home wasn't just a town; it was a guy who was willing to stop running and build a life right there on the shore.