Laci J. Mailey gained prominence in the entertainment industry when she took on the role of Jess O’Brien-Peck in the popular American-Canadian drama series “Chesapeake Shores,” which aired on the Hallmark Channel. The cable network announced before the premiere of the sixth season last August 2022, that it would be its final season; fans were devastated by the news, as it was the favorite Sunday companion of many. Due to the many struggles that Jess had over the years, viewers were curious if she ended up happy with her life. Several rumors surfaced online about a few characters having a baby in the finale episode, including Jess, and fans were confused due to rumors of her getting pregnant in real life. Was it a case of life imitating art?

Chesapeake Shores' Laci J. Mailey

Posted by Hallmark Channel on Thursday, August 3, 2017

All about “Chesapeake Shores”

Hallmark drama series “Chesapeake Shores” might have chronicled the lives of the multi-generational O’Briens family in the six seasons that it had been on TV, but the story started rolling when Jess O’Brien called her older sister Abby O’Brien Winters, and asked for her help to avoid foreclosure on her newly bought inn. To do that, Abby would need to return home and face everything and everyone whom she’d tried so hard to forget. It was a series about revisiting old wounds, getting second chances, and examining life choices.

A TV adaptation of a novel series

The drama TV series was inspired by the works of New York best-selling author Sherryl Woods. Of the 14 books of the “Chesapeake Shores” series that she wrote, around 13 were already published by the time the first episode was aired – she only added the 14th book in 2017, when the series was in its second season. Fans were delighted that the TV writers gave some positive spin to the development of some of their beloved characters in the screen version. It made them more relevant and relatable, as the first book was published back in 2009. Sherryl was credited as one of the executive producers of the drama series.

The main cast of characters

The ups and downs of the O’Briens, an Irish-American family, were front and center of the drama series. The head of the family, Mick O’Brien (Treat Williams), was an accomplished real estate contractor and developer, who thought that the best way to protect his family was to be a great provider. However, success came at a price, as his wife, Megan O’Brien (Barbara Niven), divorced him as he didn’t have enough time to nurture their marriage. To avoid uprooting their five children, she opted to leave them in Mick’s care, and moved to New York to start a new life.

The O’Brien children were comprised of the fierce Wall Street financial analyst Abby, the practical yet caring US Army medic Kevin (Brendan Penny), the flamboyant yet insecure playwright Bree (Emilie Ullerup), the smart and eager to prove Connor (Andrew Francis), and the bullheaded but flighty inn owner Jess (Lacy J. Mailey). The divorce and the abandonment by their mother left all of them with scars, some deeper than others. The eldest was only 17 when it happened, and their father realized too late that his attitude of being emotionally unavailable worsened the situation. Mick’s mother, Nell O’Brien (Diane Ladd), the matriarch of the family,  did her best to ensure that all her grandchildren were taken care of.

Jess O’Brien’s journey in “Chesapeake Shores”

She was way in over her head with her new investment

The fifth child in the O’Brien brood found herself calling for Abby to extricate her from difficult situations, just as she’d always done over the years. Jess was the bubbly one in the family, but who hadn’t found her calling, changing jobs frequently until she bought an old, run-down inn. However, she maxed out her card buying expensive equipment that she couldn’t afford, as she wanted to turn the inn into a bed and breakfast. Their grandmother told Abby, ‘It’s not your responsibility to fix it. You’ve been rescuing that girl since the day that your mother left.’ Nevertheless, Abby stepped in and helped Jess with her loan extension with the bank.

Her resentment toward her parents

Even now as an adult, Jess harbored resentment toward her parents for abandoning her when she was just a child; she couldn’t believe that Abby continued to have a good relationship with both of them. Her oldest sister told her that their mother didn’t abandon her, as she just moved to another state. She explained that Megan wanted to bring all of them with her, but felt that it would be better to not uproot them since they were all still studying at that time.

Jess then asked Abby if there would be any type of situation that would make her leave her children, and her sister couldn’t say anything to that. However, Abby reminded her that they were no longer children, but the younger O’Brien asked her at what age did anyone stop needing their father and mother. She realized how pathetic she sounded, because she was still waiting for them to come home after all these years.

Mick offered to help Jess with her B&B renovation problems

The problem with Jess’ new investment was that she didn’t know anything about hotel management, and that she insisted that it wasn’t a hotel but just a B&B. She believed that it wasn’t something that complicated to manage, since it was like having sleepovers that pay. When she came home, she found her father tinkering under the kitchen sink. He said he wanted to check out the house, but acknowledged that it was a prime location for a bed and breakfast.

Except for some piping problems, the house was in good condition, and Jess was surprised at his house evaluation. Apparently, Mick and his father had built their house together, so he knew exactly the quality of its construction. Jess initially rejected his offer of help, but quickly reversed her decision. Mick told his youngest daughter that he was proud of what she’d achieved but that he never said it enough. Jess said it was all right, but Mick said, ‘No it wasn’t okay and that they need a lot of catching up to do,’ saying fixing the house would give them lots of time to do it.

Uneasy relationship with her mom

From the get-go, it seemed that out of all the O’Brien children, it was Jess who had a hard time dealing with their mother. Megan tried reaching out to her daughter, but the latter continually shut down all her attempts to reconnect. The problem was that when Megan returned to Chesapeake Shores, Jess couldn’t adjust to having her mother around, and would constantly blame her for everything that went wrong in her life. Her siblings, especially Abby, thought that it was time for Jess to grow up and confront her fears. Eventually, the relationship slowly improved, with Jess opening up to her mom. It was a difficult journey because she had abandonment issues, and it only became easier when she accepted that she needed to focus on the present, and not the past.

Her one constant nightmare

When Megan stayed in Jess’ B&B for the duration of her visit, it was an awkward time for both of them. Before their separation, it was a morning habit of the mother to ask her daughter about her dreams the previous night. When Megan tried doing that again, Jess rebuffed her mother’s attempt to recreate what they had before, saying that she didn’t dream anymore.

Apparently, she had this one constant nightmare since she was a child that continued to bother her, due to the sea mishap that she was involved in during a school trip when she was in grade school. The ship sank, and she ended up in the water along with many of her classmates. She always felt guilty that she couldn’t get to her other classmates in time.

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When Jess met David

Jess and Bree loved each other to bits, but their relationship almost took a nosedive when they realized that they were both interested in the same man, David Peck. Jess gave way since she recognized that her sister and David had more things in common, but it turned out that David was into her, not Bree. Things became more complicated when Jess hired him as B&B’s resident chef. They both liked each other, but she was afraid to take their relationship to the next level, as it would ruin the friendship that they both treasured.

Eventually, Jess and David became a couple, but it was almost destroyed because he kept a secret from her. David actually came from a wealthy family in Maine, which was the reason why it didn’t matter to him that he wasn’t paid well as a chef. He really wanted to tell her, but hesitated since he didn’t want anything to change between them. David confessed that he was treated differently when he was in Maine, but enjoyed his anonymity in Chesapeake.

The not-so-successful ‘meet the parents’ stage

When David was requested by his parents to return home and he complient, Jess thought that it was all over between them. However, David wasn’t breaking-up from her, as the only reason he was leaving the B&B was that he needed to take care of his ailing father. Later on, David invited Jess to meet his parents and sister, Alexandra, in Maine, and Bree accompanied Jess for moral support.

When they arrived, Jess started to doubt if David really loved her when she saw how huge David’s estate was. It was also announced at the family dinner that David was chosen to take the reins of the family business, to Alexandra’s disappointment. When Jess learned that his parents had her investigated, she was devastated. She confronted David’s parents about it, and they justified it by telling her that they wanted the best woman for their son. As it became obvious that they were trying to find ways to separate the two, Jess and Bree immediately left that night for Chesapeake Shores.

David made Jess feel like Cinderella

David wasn’t interested in being the CEO of their family business, telling his parents that he loved the life he’d built in Chesapeake. Jess was in such a hurry to leave Maine that she didn’t notice that David followed her, and was trying to get her attention. She was so heartbroken that she also didn’t realize that she left one of her shoes behind when she hopped into the cab that night.

When David went back to Chesapeake, he took that shoe with him, slipped it onto her foot, and declared that he wanted to be with her – just as Prince Charming did with Cinderella. After they shared a kiss, he told her that he wanted to keep on working for the B&B, and be with her if she would have him.

David’s parents offered an olive branch

Jess’ B&B was condemned by the city’s safety inspector due to termite infestation, and so she didn’t have any choice but to close her business. During The Regatta event in Chesapeake, David’s parents dropped by and offered an olive branch to the couple, to make up for what they did to Jess when she visited them.

When they learned what happened to the business, they proposed to give them their own B&B located in Tanglewood, Maine. It was also their way to get their son back. Initially, their offer was rejected, but David later gave his parents another chance. However, it didn’t work out well, because his parents meddled in their business. They realized that it would be best if they built their own, back in Chesapeake.

A new B&B in Chesapeake Shores

After the fallout of the business in Tanglewood, they bought a new inn in Chesapeake, and turned it into a B&B. The two had to deal with their opposing views on several things while building the business, but they learned to compromise to reach a common goal. They also encountered many problems along the way, including a visit from a local city official, as they operated without a license. Apparently, some guests had arrived days before the opening of the inn, and they scrambled to accommodate them, but that decision led to a substantial fine that they needed to pay, because at that time, the period of their license hadn’t yet started.

When they asked for leniency, they were told that they needed to file for five appeals and wait for the city council to review them, which would take a month or two. Jess couldn’t even wait for 24 hours to pass before talking with a city official to appeal their case. Initially, the man was so adamant that he couldn’t be persuaded to do anything inappropriate, but he wasn’t a match to Jess’ persuasive powers. She was even crying after their meeting, which confused David and Bree who were waiting for her. While the show never gave any details about what went through, it was assumed that Jess touched the heart of the city official by sharing her love story. They were then back in business as scheduled.

Was it a happy ending for Jess and David?

A proposal and a wedding

All the while David was busy preparing for the official grand opening of the inn, he already had plans to propose to Jess, but couldn’t find the right moment; he didn’t know that Jess accidentally discovered the ring while rummaging through one of the kitchen drawers. There was even a funny incident in which she thought he was about to propose, as he was down on his knees tending the garden when he asked her a question, only to find out that it was all about parking. Later on, David baked a pie for her to taste, and then she discovered the ring hidden in the middle of it – he proposed and she said yes.

A few days before their wedding, Jess had ridiculous nightmares of something bad happening with her groom, such as being struck by lightning or being swallowed by the ground, or even being taken by a giant squid. However, the couple exchanged wedding vows with their loved ones in attendance, without any horrible interruptions.

Jess and David were pregnant

In the past, Jess was hesitant about getting pregnant, because she felt that she wasn’t ready to become a mother, so they never tried. When she fixed everything about herself, she told her husband that it was time for them to have a baby. David was on board with the plan, and thought they were just about to try, but Jess told him she took eight pregnancy tests and they all came out with positive results. David was ecstatic about the news and couldn’t wait to share it with everyone.

Most “Chesapeake Shores” fans were confused if the baby announcement in the show was inserted into the narrative because Laci J. Mailey, the actress who played the role, was pregnant in real life. Apparently, that wasn’t the case, as Laci gained weight after delivering her second child. The drama series gave Jess a wonderful ending, as she was in a great place as a person. She was healed as she’d reconnected with both of her parents, her business was doing great, she found an amazing husband, and was about to become a mother.

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