Chesapeake Shores Season Five Premiere Teasers: Abby Reflects on Her Relationship With Trace — and a Major Conflict of Interest Surrounds the O’Brien Family

Chesapeake Shores season five O'Brien siblings bar Hallmark

Wedding plans, an intriguing job offer and a big return kick off the summer drama.

It’s the moment Chessies have been waiting for — the season five premiere of Hallmark’s Chesapeake Shores! Soaps.com will be bringing our readers weekly teasers into what’s ahead for each new Sunday episode, which airs at 8 pm, beginning on August 15.

We’ve given viewers a preview of this season’s love, heartache and new beginnings and now we have an inside look into what will go down upon the series return on Sunday. Season four left us with a kiss cliffhanger between Abby and Trace, so she’ll find herself reflecting on their long relationship, as well as what it means for the future.

With David and Jess engaged, wedding plans are in the works, but the location is set — Chesapeake Shores. However, David’s family puts a damper on things when they present Jess with a legal document, which leaves her very much on edge. Could a pre-nup be in order?

More: A major character exits Chesapeake Shores

And what about Bree? She’s been away in London working on her play, but returns to town fresh off its run. Though an intriguing job offer presents itself, it will mean having to reunite with her high school nemesis. Will the pros outweigh the cons?

Then there’s Connor… the law firm he now works for may be representing a new client — one that could pose a major conflict of interest for the O’Brien family.

Want more? You can view photos from the episode in our season five Chesapeake Shores gallery below, which we will update each week for a closer look into the family drama.

Get more Hallmark news — and your free daily soap-opera fix — delivered straight to your email inbox by signing up for Soaps.com’s newsletter.

Video: Hallmark Channel/YouTube

Chesapeake Shores season five David Hallmark

Chesapeake Shores season five Robert Buckley Hallmark

Chesapeake Shores season five Raylene Harewood Hallmark

Chesapeake Shores season five Trace The Bridge bar Hallmark

Chesapeake Shores season five Abby at The Bridge bar Hallmark

Chesapeake Shores season five Kevin ponders Hallmark

Chesapeake Shores season five Connor and Bree laugh at the bar Hallmark

Chesapeake Shores season five Jess and Mick Hallmark

Chesapeake Shores season five Jess with David's parents Hallmark

Chesapeake Shores season five Connor's law firm Hallmark

Chesapeake Shores season five Mick gives Trace advice hallmark

Chesapeake Shores season five Bree and Luke at the donations box hallmark

Chesapeake Shores season five Abby and Trace on the docks hallmark

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megan shows mick painting season five Chesapeake shores hallmark

Mick and Abby meet with Evan season five Chesapeake shores hallmark

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kevin and bree talk park bench season five Chesapeake shores hallmark

Chesapeake Shores season five mick and thomas hike hallmark

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Chesapeake Shores season five snally hunting creature hallmark

Chesapeake Shores season five connor and abby find evidence hallmark

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Chesapeake shores season five kevin, david, connor triathlon hallmark

Chesapeake shores season five bree, jess, abby triathlon hallmark

Chesapeake shores season five jess and david sit at inn hallmark

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Chesapeake shores mick and guests at david and jess' wedding hallmark

Chesapeake Shores evan stays at abby's Hallmark

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Chesapeake Shores evan hurts back Hallmark

Chesapeake Shores sarah and kevin hospital Hallmark

Chesapeake shores nell talks to mick hallmark

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Chesapeake shores evan takes abby on a trip hallmark

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Megan job Cali Chesapeake Shores Finale Hallmark

Connor, bree, luke parole case Chesapeake Shores Finale Hallmark

Margaret and Connor Chesapeake Shores Finale Hallmark

abby and evan lunch Chesapeake Shores Finale Hallmark

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Chesapeake Shores Season Five Premiere Teasers: Abby Reflects on Her Relationship With Trace — and a Major Conflict of Interest Surrounds the O’Brien Family

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<p>Carlo Marks returns as David. It’s time for him and Jess to plan their wedding!</p>

<p>Robert Buckley makes his debut in season five. Oh, and did we mention, he’s a billionaire?</p>

<p>Raylene Harewood makes her debut in season five. She works with Connor at the new law firm. </p>

<p>In the season five premiere on Sunday, August 15, Abby imagines Trace standing behind the bar at The Bridge. Abby — and their season four cliffhanger kiss — is on her mind.</p>

<p>Abby’s at The Bridge with her family. Her future with Trace, and thoughts of their past, consume her.</p>

<p>Abby’s brother Kevin seems to be pondering his future as well. He and wife Sarah are planning new beginnings of their own.</p>

<p>The other O’Brien siblings, Connor and Bree, reconnect. Bree’s back home after working on her play in London.</p>

<p>Sister Jess spends some time with their father Mick. She is about to welcome some visitors to town.</p>

<p>Jess brings her fiance David’s parents to the docks. They’ll soon present Jess with a legal document that will having her feeling on edge.</p>

<p>Connor is working at a new law firm. However, a possible new client will turn out to be a conflict of interest where his family is concerned.</p>

<p>In the Sunday, August 22, episode, Mick and Trace take some time out to connect at The Bridge. Mick is giving him advice, as he often does. </p>

<p>Bree meets up with someone from her past while making a donation. Luke is her brother Kevin’s friend from high school. </p>

<p>Abby and Trace are at the docks. Considering Trace is leaving town, this could be one of the last close moments we see between them — even though it’s another one of Abby’s reflections on the past.</p>

<p>Abby and Mick have partnered up at O’Brien Construction. They have a business problem on their hands and are losing clients.</p>

<p>In the Sunday, August 29, episode, Megan shows Mick a painting, which he buys for her for eight dollars. Considering how valuable it really is, she plans to locate its artist.</p>

<p>Mick and Abby meet the local billionaire at the job site. Given the lawsuit looming over O’Brien Construction, they do their best to make sure Evan doesn’t back out of the hotel project.</p>

<p>Evan’s goofy ways seems to get under Abby’s skin. Here he appears to be spending the afternoon doing some rock climbing.</p>

<p>Siblings Bree and Kevin catch up over coffee. Between Kevin worrying about his chief at the station and Bree dealing with faces from the past, Luke’s return to shore is likely brought up. </p>

<p>In the Sunday, September 5 episode, Mick and his brother Thomas reconnect — and what better way to do it? The brothers set off to hike the Appalachian Trail to recreate a childhood memory. </p>

<p>Back at the Shores, Jess and David lead a group into the woods for the annual Snally Hunting Weekend. Everyone is on the lookout for the infamous Snallygaster.</p>

<p>This looks like an owl to us, but could it be the mystically creature at the center of the hunt? Only time will tell.</p>

<p>Abby and Connor are at opposite ends of the battle regarding the Dilpher case. But blood runs thicker than business, and the siblings find evidence that could help exonerate their father.</p>

<p>In the Sunday, September 12, episode, Sarah receives some very unexpected news. Good thing Jess is there to wrap her sister-in-law in a hug for comfort.</p>

<p>It’s time for Chesapeake Shores Day — and we have some winners! Kevin, David and Connor smile after winning medals in the triathlon.</p>

<p>It looks as though it’s a double celebration for the O’Briens. Jess, Abby and Bree take home medals too!</p>

<p>There’s nothing better than relaxing with a glass of wine. That’s exactly what David and Jess are doing at their inn.</p>

<p>In the Sunday, September 19, episode, Abby takes time out for herself at karate class. Her workouts have proven to help release some of the tension caused by Evan and the hotel project.</p>

<p>It’s time for Jess and David’s wedding day. Bree has picked a plus-one but did a guest list fiasco prevent her from bringing Luke? </p>

<p>Part of the wedding party has arrived. Connor, groom-to-be David, Mick and Kevin look handsome as ever in their suits.</p>

<p>And talk about a proud papa… just look at Mick as he waits for the ceremony to begin. Everyone else looks happy to be celebrating the big day with Jess and David too.</p>

<p>In the Sunday, September 26, episode, Abby and Evan do some work at the O’Brien residence. Little did she know that he would end up hurting his back.</p>

<p>Since the occurrence happened at the O’Brien’s, Evan is invited to stay until he feels better. It’s safe to say the couch will be occupied for a few days.</p>

<p>Everyone carries on as usual. Nell, Abby and the girls share a meal while Evan gets caught up on work from their couch.</p>

<p>Sarah lands in the hospital. While waiting for further tests, the news they received at the firehouse could very well affect their plans to start a family.</p>

<p>In the Sunday, October 3, episode, Nell and Mick share a close moment. The loving mom just might have more advice for her son.</p>

<p>Evan’s driver arrives at the O’Brien house. For what? To whisk Abby away on an adventure.</p>

<p>This beautiful place awaits Evan and Abby’s arrival. Could it be one of many of the billionaire’s properties or something more? </p>

<p>While seated amid tea and sandwiches, Evan has something to tell Abby. Will she be receptive to his declaration? </p>

<p>In the Sunday, October 10, episode, Megan struggles with an inner battle, as news of Mick’s whereabouts is unknown. However, she must pull it together for the art show.</p>

<p>Arthur and Nell attend the art show together. In fact, the two old friends take some time out for a dance.</p>

<p>Connor is completely exhausted and stressed over starting his own business. He knows he needs help in the form of an assistant.</p>

<p>Evan has a lot on his mind, mostly Abby, and makes a grand gesture. Too bad his generosity ends up backfiring.</p>

<p>In the Sunday, October 17 season finale, Megan is supposed to be planning a trip around the world with Mick. However, an opportunity could take her to California, which will likely put a damper on their plans — and their future.</p>

<p>Connor works to help Luke fight his parole hearing. If he fails, Luke could be headed back to prison.</p>

<p>Margaret is worried about Connor’s stress levels and his health. She plans to help him relax with a little surprise — one that he will be sure to love. </p>

<p>Evan finally gets up the nerve to ask Abby out on a date. Will she say yes or are her feelings stronger for Jay? </p>

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