Jess O’Brien has overcome a lot — the challenges of attention deficit disorder, the near bankruptcy of her beloved Inn at Eagle Point and her self-perception as a screwup in a family of overachievers. Now she’s ready to share the future with a man. Her friends persuade her to join a dating...
Jess O’Brien: For years Jess, youngest daughter of Mick % Megan O'Brien, successful owner and manager of the Inn at Eagle Point, has coped with abandonment issues and having ADD and its problems - disorganization, commitment, boredom, distractability. Psychologist Will has been in love with her since they were 14.
Will Lincoln: He is a pyschologist who is in love with Jess O'Brien. He is calm, patient, romantic and loves to have a good time!
Mick O'Brien: The patriarch of the Chesepeake Shores Series, Mick is the father of Jess O'Brien and her four older siblings. Strong willed & loving, Famous architect, who, with his brothers Jeff and Thomas, created and built Chesapeake Shores. he wants everything to go his way and isn't above making it happen by meddling, or speaking his mind. Remarried to Megan O'Brien
Mack: Mack is a good friend of Will. He is self motivated and a self starter and urges other to take action on their behalf that pushes him to strive his best! He has a ladies man reputation and works for a newspaper
Jake Collins: Jake is a good friends of Will, Mack and Trace. Married to the next to youngest O'Brien daughter Bree (who owns "Flowers On Main") Brother of Connie Collins. Runs a Landscaping business and nursery. Jake and Bree have a new daughter.
Laila Riley: she is a outgoing women who stands her ground! she is Jess O'Brien's friend... And Abby's husband, Trace's Sister.
Gail: she is the chef of the Inn at Eagle Point and she is a good listener & Friend. Promotes ditsy young man close to being fired at the inn.
Thomas O’brien: Twice married and divorced brother of Mick and Jeff O'Brien without children of his own. A dedicated environmentalist who is interseted in Connie Collins.
Abby O'Brien Winters Riley: Abby is Jess O'Brien's oldest sister. She is Jess's strongest advocate, a good financial planner. She worries about Jess. Mother of twin daughters from her first marriage, now married to Trace Riley.
Gram, Nell O'Brien: gram is the good cook who raised jess o brien and her siblings! Mother of Mick, Thomas, & Jeff, Grandmother & Great Grandmother of the O'Brien Family. Wise and loving matriarch of the family.
Ronnie Forrest: underachiever close to being fired from yet another job, when Gail see potential in him in the kitchen of The Inn at Eagle Point
Kevin O'Brien: Kevin is the 2nd oldest of the O'Brien siblings. Married to Shannah. Mick O'Brien's oldest son owns Harbor Lights
Heather O'Brien: Conner's wife and mother of their son, little Mick. She owns and runs Country Quilts in Chesapeake Shores next to Megan;s art gallery.
Megan O'Brien: Remarried to Mick O'Brien, mother of Abby, Kevin, Bree, Conner, & Jess whom she abandoned when Jess was 7. She regrets everything she has done in the past.and is trying to reestablish bonds with her now grown children.
Bree O'Brien Collins: Mick & Megan's O'Brien's middle daughter owns flower shoppe "Flowers on Main", married to Jake Collins, has infant daughter.
Sally: Owns the little restaurant that is a key meeting place in CS stories
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