‘Chesapeake Shores’ Season 5 Finale Ends on a Shocking Note for an O’Brien (RECAP)

[Warning: The below contains MAJOR spoilers for the Chesapeake Shores Season 5 finale “That Old Feeling.”]

Going into the Chesapeake Shores finale, obviously everyone has one question on their minds: Who will Abby (Meghan Ory) choose — Evan (Robert Buckley), Jay (Greyston Holt), or neither? “That Old Feeling” addresses just that, but not in a way fans might expect.

Evan’s finally realized he wants to ask Abby out and decides to make the grandest of gestures: picking her up from the airport. (Yes, he drives.) They stop for lunch, and that’s when he asks her out for “a full-on date.” She’s leaning towards keeping it professional, but he convinces her to sleep on it. She’s “confused,” she admits to her sister Bree (Emilie Ullerup). He annoys her and drives her crazy, but she might be interested. And he certainly endears himself to her when he brings dairy-free brownies for her daughter.

But what about Jay? He seems to be winning Abby over when he tells her about capturing perfect moments with his camera… including a photo of her. He tells her he has feelings for her, but he also likes a guidance counselor at the school. He might want to start something with her unless Abby can tell him there’s hope he gets out of the friend zone in the future.

That leaves Abby with a lot to think about, and she tells Bree, “I don’t know if I want to be with either of them. I don’t know if I want to be with anyone right now.” But then she calls someone to leave a voicemail saying, “I have been thinking about you and I think maybe we should give this a try.” But who did she call?!

We may not know what’s going on with Abby’s love life, but another O’Brien’s relationship status does change in the finale: Connor’s (Andrew Francis), with the moment we’ve been waiting for since we met Margaret (Raylene Harewood). As she forces him to rest, with a mini s’mores kit and tiny firepit. Their hands touch when they reach for the marshmallows, and they kiss!

David Astorga /Crown Media

And they’re kissing again, in the driveway of the O’Brien house at the end of the episode when Connor suddenly collapses, possibly having a heart attack. Margaret yells for the rest of the family, and they call 9-1-1. Uh-oh!

Elsewhere for the O’Briens:

• Sarah (Jessica Sipos) had a miscarriage, and while she doesn’t want Kevin (Brendan Penny) to tell anyone, he confides in his parents about his pain. Then, his mother Megan (Barbara Niven) goes to see her daughter-in-law and assures her she can only get past this at her own pace, just like she did. The pain and grief don’t go away, but the sharpness does dull and you learn your own strength.
• Connor realizes what led to that false positive on Luke’s (Stephen Huszar) drug test: an over-the-counter sleep-aid, combined with an antihistamine. With that and an expert witness (in the form of Connor’s doctor), Luke wins his case against his parole officer.

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• Mick (Treat Williams) and Megan are planning to travel around the world together… until her ex, Carter (Barclay Hope), tells her about a job at the Getty in Los Angeles. She’s ready to turn down her dream job, but Mick pushes her to really think about it. She comes up with a plan, arranged by Carter: work at the Getty a year, then six months off to travel with him. Mick wonders if her ex has set this up to have her there with him. Can’t he trust her, Megan asks. “Trust you not to leave me again? I don’t know if I can,” he says. Ouch!
• Should we be worried about Mick possibly taking too many painkillers?
• Jess (Laci J Mailey) writes her mom a 3 a.m. “honest” email, one that leads the two to have a talk they’ve needed to. Jess is happy her parents are back together, but Megan knows she can’t make up for leaving her when she needed her. She’ll spend the rest of her life making sure her daughter knows it wasn’t her fault.
• David’s (Carlo Marks) dad cleans out his trust fun and flees the country. The feds are looking for him for wire fraud and embezzlement.