Dating history of the ‘Chesapeake Shores’ cast: photos

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Calling all Chessies! Hallmark Channel fans have laughed, cried and loved alongside the cast of Chesapeake Shores since 2016 — and off screen, fans have become just as intrigued by the stars’ friendships and love lives.

When Chesapeake Shores debuted, viewers were introduced to the lovable O’Brien clan after eldest sister Abby O’Brien (Megan Ory) moved back home after her divorce. With her two children in tow, Abby was reunited with sisters Bree (Emily Ullerup) and Jess (Laci J Mailey), as well as brothers Kevin (Brendan Penny) and Connor (Andrew Francis).

The family wouldn’t be complete without mom Megan (Barbara Niven) and daddy Mick (Treat Williams), who often set a good example of what true love looks like. The romantic ups and downs of all the O’Brien kids have captivated fans season after season, with Abby’s love life being a major focus.

May 2021, Jesse Metcalfe, who played Abby’s high school sweetheart Trace Riley, surprised viewers when he announced his departure after five seasons. “I tailored that role for me,” Metcalfe exclusively told me Us weekly in October 2020, prior to his final bow. “I mean, the series is based on a series of books, where the character is an architect. So I was given the freedom to completely change the character and type of makeup [him] like, [me].”

New love interest Evan Kincaid (played by Robert Buckley) quickly filled the void, but left many fans wondering if Abby would find her happily ever after. In August 2022, Chessies got their answer as the sixth and final season of the beloved series began.

However, the 10-episode finale wasn’t the last fans of the O’Brien clan would see – because the cast are good friends outside of the show. In fact, many of the stars have already jumped bandwagon after filming the series.

“Well that’s a wrap on #chesapeakeshores after 6 seasons! I started this season with #hyperemesisgravidarum and ended with #covid – it’s been quite the run! Orie wrote via Instagram in July 2022. “Thank you so much to our amazing cast and crew for being so patient with me while I tried not to puke on anyone.”

The There was once alum also gave her a “great” husband John Reardon a shout out for “holding the fort and being my rock.” She added: “And our two, yes two Nannies for all their support. With mom and dad both on TV shows, having two Nannies was a must! #ittakesvillage. I hope everyone watching enjoys the final season! Xo.”

Ory’s TV sister Ullerup also got it sentimental after parting from her working family that same month. “For six years I got to play the daughter, sister and brother of these wonderful, crazy people. It’s the longest running job in my career,” she captioned a group photo. “So much has happened in our make-believe world and also in our personal lives. It was a great cushion to have an entire second family to share the ups and downs with.

The Love & Glamping actress – whose real husband Kyle Cassie appeared in several episodes of the show as Martin Demming concluded, “I know they will all achieve great things as they are really talented people. I will be forever grateful for everything #chesapeakeshores has gifted me. What a great run, fam.”

Scroll down for a complete guide to the cast’s real-life romances: