The Last Goodbye Characters

Owner and chef of Bennett's on the Bay in Blue Sky Bay, fiercely protective of his restaurant and employees. He raised his younger sister Jovi and values self-reliance, loyalty, and showing up daily. He is close with Cutler, Cannon, Brody, and Phoenix, and becomes Briar Sinclair's partner and fiancé.

Arc: He begins seeing Briar as his 'worst fucking nightmare' and refuses to sell or relocate, but after negotiating a deal he apologizes, falls for her, supports her through family betrayal, flies to New York, and proposes marriage. He learns to let love and home into his life.

• Briar Sinclair — business adversary turned romantic partner and fiancée; he calls her Magpie and she calls him McGrumpy
• Jovi Bennett — younger sister he raised and whose college tuition he paid
• Cutler Heart — best friend
• Cannon Jones — close friend and brother figure
• Brody — best friend
• Phoenix — close friend
• Winona — general manager at his restaurant
• Dean — bartender at his restaurant
• Jenna Bennett — estranged mother
• William Winchester — business adversary and father of Briar
• Celine — ex-girlfriend
• Clover — calls him Uncle B

A real estate attorney and project manager for Winchester Investments, and William Winchester's biological daughter. She was raised by her mother Josephine and Granny Sinclair and did not meet her father until college. She arrives in Blue Sky Bay to buy or relocate Bass's restaurant, initially pretending to be pregnant to force a meeting.

Arc: She moves from corporate negotiator trying to force Bass out to someone who fights for Bass and the town. After uncovering her father's betrayal, she uses her mother's letters as leverage, negotiates 51% ownership of the Blue Sky Inn, rejects needing her father's approval, and becomes Bass's partner and fiancée.

• Bass Bennett — business adversary turned lover and fiancé; he calls her Magpie and she calls him McGrumpy
• William Winchester — biological father and employer with a complicated relationship
• Josephine Sinclair — mother, deceased
• Denton Winchester — half-brother
• Tabitha Winchester — stepmother who resents her
• Gracie — friend
• Tatum Monroe — friend
• Steven Hansen — colleague and architect who hits on her
• Jenna Bennett — helped her get to Jovi's graduation
• Jovi Bennett — friend
• Cutler Heart — friend and colleague

Briar's biological father, co-founder and president of Winchester Investments, and a business shark focused on profit and image. He is emotionally cold and withholding, and he knew about Briar long before she met him. He makes a secret side deal with K&R for a larger hotel.

Arc: He presses Briar about the deal, makes a side deal behind her back, is exposed by Josephine's letters, and ultimately agrees to Briar's terms for the Blue Sky Inn, including her 51% ownership. He asks to continue a relationship and says he is proud of her.

• Briar Sinclair — daughter
• Josephine Sinclair — former affair partner and mother of Briar
• Denton Winchester — son
• Tabitha Winchester — wife
• Steven Hansen — employee and architect
• John Palluso — business associate
• Bass Bennett — adversary and father of his daughter's partner

William's wife, co-founder of Winchester Investments, and Briar's stepmother who despises her. She demanded a paternity test when Briar met the family and resents Briar being at family holidays. She is concerned with appearances and is hostile toward Briar and Briar's deceased mother.

Arc: She insults Briar and her mother, controls the family image during the magazine interview, and is confronted by Bass. Denton later confronts her about how she treated Briar, but she remains resentful.

• William Winchester — husband
• Briar Sinclair — stepdaughter she resents
• Denton Winchester — son
• Jessica — future daughter-in-law
• Bass Bennett — dismisses him as a cook and is confronted by him

Jenna Bennett's boyfriend who beat Jovi, giving her a fat lip and black eye. Bass hit him back, and Ray threatened to press charges against Bass. Jenna left with Ray after the abuse.

Arc: He remains a past source of trauma for Jovi and Bass, shaping their distrust of Jenna and their protective family dynamic.

• Jovi Bennett — abused her
• Bass Bennett — Bass defended Jovi against him
• Jenna Bennett — boyfriend

Bass's younger sister, who is graduating at the top of her class and plans to spend six months in Italy. She was abused by Ray, her mother's boyfriend, and still hopes her mother Jenna can change. She is close with Bass, Cannon, and Gracie.

Arc: She graduates, leaves for an Italy internship, worries about Cannon at the PBR finals, and tells Bass to start living. She remains hopeful about her mother even after Jenna's struggles.

• Bass Bennett — older brother and guardian
• Jenna Bennett — mother
• Ray — mother's boyfriend who abused her
• Cannon Jones — close friend
• Gracie — friend

Bass's best friend, Gracie's fiancé, and a contractor/architect who is River's nephew. He helps Bass with legal and renovation advice and is honest when Bass is being an asshole. He is part of the close group of friends around Bass.

Arc: He supports Bass's restaurant deal and renovation, confronts Glen Forest about the larger hotel plan, and advises Briar that love is more powerful than loss. He builds a house with Gracie on the same street.

• Bass Bennett — best friend
• Gracie — fiancée
• River — uncle
• Briar Sinclair — friend and colleague
• Tatum Monroe — friend
• Cannon Jones — friend
• Brody — friend
• Phoenix — friend

Bass's close friend and brother figure, a charming PBR rider who teases Bass about Briar. He competes in the PBR World Finals despite broken ribs and a broken hand. He is close with Jovi and the rest of the friend group.

Arc: He finishes second to Sebastian Lee, handles the loss with grace, recuperates at Phoenix's house, and continues supporting Bass and teasing him about Briar. He accepts the loss and plans to return.

• Bass Bennett — close friend and brother figure
• Jovi Bennett — close friend
• Phoenix — friend
• Brody — friend
• Cutler Heart — friend
• Sebastian Lee — competitor

Bass's best friend, a bartender at Four Clovers, father of Clover, and Phoenix's brother. He is loyal to Bass and initially hostile to Briar, but later teases Bass and supports him. He cares for Tatum and contacts Phoenix when she seems off.

Arc: He moves from suspicious of Briar to friendly teasing, calls Bass out when he is wrong, and helps Tatum by texting Phoenix when she is upset. He remains a steady friend and father.

• Bass Bennett — best friend
• Clover — daughter
• Phoenix — brother
• Tatum Monroe — childhood neighbor and friend
• Gracie — friend
• Cutler Heart — friend
• Cannon Jones — friend

Bass's close friend, Brody's brother, and Tatum's childhood neighbor and close friend. He is cynical, protective, and sometimes called Nix. He hosts game night and later cares for Cannon while he recuperates.

Arc: He moves from group-chat cynic to caring for Cannon and supporting Tatum; when Tatum learns Raelyn has died, he comforts her and insists on driving her to the attorney meeting. He remains protective and suspicious of strangers.

• Bass Bennett — close friend
• Brody — brother
• Tatum Monroe — childhood neighbor and close friend
• Cannon Jones — friend
• Cutler Heart — friend
• Raelyn — former neighbor

Cutler's fiancée and a warm, welcoming friend to Briar and Tatum. She helps Briar with design choices, invites her line dancing, and defends her when Brody turns hostile. She has a bulldog named Meatball.

Arc: She befriends Briar, supports her relationship with Bass, chooses her wedding dress, and urges Bass not to quit on Briar. She remains a steady, caring presence in the friend group.

• Cutler Heart — fiancé
• Briar Sinclair — friend
• Tatum Monroe — friend
• Bass Bennett — long-time close friend
• Meatball — dog
• Presley — mother
• Emerson — Cutler's mother

Gracie's friend and Briar's friend, friendly, curious, and never met a stranger. She is a childhood neighbor of Phoenix and Brody and the stepsister of Raelyn. She has been searching for Raelyn and learns Raelyn died and named her to care for son Oliver.

Arc: She moves from line dancing and gossip to grief and shock after learning about Raelyn's death and will. Phoenix supports her as she considers caring for Oliver.

• Gracie — friend
• Briar Sinclair — friend
• Phoenix — childhood neighbor and close friend
• Brody — childhood neighbor and friend
• Raelyn — stepsister
• Oliver — Raelyn's son, whom Raelyn wanted in her care
• Jonathon — work contact

General manager at Bennett's on the Bay who has worked for Bass for three years. She is curious, amused, and loyal, and she often delivers important news to Bass. She supports Bass when he leaves to find Briar.

Arc: She remains a steady presence at the restaurant, covers for Bass when he leaves, and helps him set up his proposal to Briar.

• Bass Bennett — boss and friend
• Briar Sinclair — dealt with her at the restaurant
• Dean — coworker
• Sally — coworker
• Joey — coworker

Briar's half-brother and colleague at Winchester Investments, son of William and Tabitha, and engaged to Jessica. He is supportive of Briar and challenges their father. He gives Briar the letters from her mother and supports her during the negotiation.

Arc: He supports Briar's plan, confronts their father for making a side deal, gives Briar their mother's letters as leverage, and praises her after the meeting. He says he loves her and plans to visit with Jessica.

• Briar Sinclair — half-sister
• William Winchester — father
• Tabitha Winchester — mother
• Jessica — fiancée
• Bass Bennett — friendly and texts him Briar's address

Bass and Jovi's estranged mother, an alcoholic who left with Ray after he beat Jovi. She claims she quit drinking and wants to attend Jovi's graduation. Briar finds her drinking at Whisper-Tails and helps her fly to New York.

Arc: She falls off the wagon, attends Jovi's graduation with Briar's help, then overindulges and makes a scene in New York. She remains fragile and estranged but wanted to be there for Jovi.

• Bass Bennett — son
• Jovi Bennett — daughter
• Ray — boyfriend who abused Jovi
• Briar Sinclair — helped her get to graduation

Cutler's uncle and an attorney who advises Bass on his lease and the Winchester Investments offer. He is a trusted legal contact for Bass. He reviews the contract and tells Bass the scenario sounds perfect for him.

Arc: He remains a helpful legal advisor, reviewing Bass's contract and supporting the deal.

• Cutler Heart — nephew
• Bass Bennett — attorney and friend

Bartender at Bennett's on the Bay who asks Bass about Briar after she leaves. He likes Briar coming in every day for a glass of wine. Bass internally forbids staff from dating her.

Arc: He remains a minor restaurant employee, curious about Briar and disappointed when she stops coming in.

• Bass Bennett — employer
• Briar Sinclair — liked her coming in for wine

An architect for Winchester Investments who flies in to review hotel plans and walk the restaurant space. He flirts with Briar, talks about Harvard, Martha's Vineyard, and polo, and invites her to dinner. Bass distrusts him and calls him a weasel and suspect.

Arc: He arrives, walks the site, delays sending plans, hits on Briar at Four Clovers, and is dismissed by her. He leaves when Briar tells him to.

• Briar Sinclair — colleague and business contact who hits on her
• William Winchester — employer at Winchester Investments
• Bass Bennett — Bass is hostile toward him

Brody's young daughter, who calls Bass Uncle B and is curious and affectionate. She asks Briar if she wants to be a mama, says she does not have a mama, and invites Briar to swim and canoe. She is excited about being the flower lady at Cutler and Gracie's wedding.

Arc: She bonds with Briar, asks Bass if he will marry Briar, and practices throwing leaves on the wedding lot. She remains a joyful, innocent presence in the friend group.

• Brody — father
• Bass Bennett — calls him Uncle B
• Briar Sinclair — new friend and Bass's partner
• Gracie — will take her dress shopping
• Meatball — plays with him

Denton's fiancée, who is friendly to Briar and supportive of Denton. She avoids conflict with Tabitha and opens up more to Briar over the weekend. She lives with Denton at the penthouse.

Arc: She greets Briar, sits with Bass during the photo shoot, leaves for brunch with Denton, and later supports Briar and Denton at the penthouse. She remains a supportive future sister-in-law.

• Denton Winchester — fiancé
• Briar Sinclair — fiancé's half-sister and friend
• Tabitha Winchester — future mother-in-law

Household staff at the Winchester estate who is warmly affectionate toward Briar. She welcomes Briar home, meets Bass, and follows Tabitha's orders during the birthday gathering. She appears to approve of Bass defending Briar.

Arc: She remains a warm staff member and ally to Briar during the family visit.

• Briar Sinclair — close household staff member
• Bass Bennett — welcomes him
• Tabitha Winchester — takes orders from her
• Peter — coworker

Household staff at the Winchester estate who greets Briar by looking her over from head to toe. He calls Bass Briar's 'special friend' and brings their bags to the room. Bass says Peter likes Briar being there.

Arc: He remains a minor staff member who appraises Briar and interacts with Bass during the Hamptons visit.

• Briar Sinclair — household staff member
• Bass Bennett — calls him Briar's special friend
• Jan — coworker

The Winchester family driver who drives Briar and Bass from the airport to the Hamptons estate. He is fond of Briar and enjoys gossiping about family drama. He reveals Tabitha's stress about the party and magazine visit.

Arc: He remains a minor but friendly figure who helps Briar and Bass arrive at the estate.

• Briar Sinclair — family driver who adores her
• Bass Bennett — drives him to the estate

Flight attendant on the Winchester private plane who greets Briar as Ms. Winchester. She flirts with Bass and clears their trays. She reveals William wrote 'Briar Winchester' on the note.

Arc: She remains a minor flight attendant who highlights Briar's complicated relationship with her father's name.

• Briar Sinclair — flight attendant on the Winchester plane
• Bass Bennett — flirts with him

Owner of the Cozy Griddle with her husband Stanley. She greets Bass, Briar, and Clover and recalls that Bass worked at the diner as a teenager. She is part of Bass's Blue Sky Bay community.

Arc: She remains a minor community figure who serves the group and connects to Bass's past.

• Bass Bennett — friend and former diner employee
• Stanley — husband and co-owner
• Briar Sinclair — serves her at the diner
• Clover — serves her at the diner

Margo Burns's husband and co-owner of the Cozy Griddle. He is mentioned as co-owner of the diner where Bass, Briar, and Clover eat.

Arc: He remains a minor background figure in the Blue Sky Bay diner.

• Margo Burns — wife and co-owner

Server at Bennett's on the Bay who tells Bass they have a full house. She also mentions that Briar Sinclair suddenly stopped coming by the restaurant.

Arc: She remains a minor restaurant employee who observes the restaurant's business and Briar's visits.

• Bass Bennett — server at his restaurant

Cook at Bennett's on the Bay who asks Bass if they are remodeling when he sees measurements being taken. Bass sends him on his lunch break and says he will explain at the staff meeting.

Arc: He remains a minor restaurant employee who is affected by the upcoming remodel.

• Bass Bennett — employee and cook

Owner of a window company and subcontractor working on the new restaurant. He tells Briar the new windows will be installed Monday and arrives with his crew to install more windows.

Arc: He remains a minor subcontractor helping complete the restaurant renovation.

• Briar Sinclair — subcontractor she meets about windows
• Cutler Heart — guides him and his crew
• Gracie — guides him and his crew

Magazine interviewer who conducts the interview with William and Briar. She asks Briar to stay after photos and questions them about their reunion. She redirects away from Tabitha's interruptions.

Arc: She remains a minor interviewer who helps expose the family's image-versus-truth tensions.

• William Winchester — interview subject
• Briar Sinclair — interviews her about finding her father
• Tabitha Winchester — Tabitha interrupts her
• Roger Wilson — works with him on the interview and photo shoot

Photographer for the family magazine photo shoot. He places his camera on a tripod and takes photos of Briar and William. He works with Flora Mason.

Arc: He remains a minor photographer in the Winchester family image-making scene.

• Flora Mason — works with her on the interview and photo shoot
• William Winchester — photographs him and the family
• Briar Sinclair — photographs her with William

A PBR competitor who needs a perfect score to keep his lead at the World Finals. He becomes the PBR World Champion and receives the gold buckle. He shakes hands with Cannon.

Arc: He wins the world championship while Cannon finishes second, serving as the competitor whose victory shapes Cannon's graceful defeat.

• Cannon Jones — competitor he has competed against for years

Doctor who informs the group that Cannon has a lot of healing to do and is being taken to the hospital for X-rays and tests. He treats Cannon after the PBR World Finals.

Arc: He remains a minor medical figure who confirms the severity of Cannon's injuries.

• Cannon Jones — doctor treating him

Lead architect for K&R Properties who tells Bass and Cutler that K&R is closing a deal to build a much larger hotel, ten or twelve stories, on the Bay Avenue lots. He says he only does the drawings and does not make the rules.

Arc: He reveals the larger hotel plan that threatens Blue Sky Bay and Bass's deal, prompting Bass to fear Briar knew and lied.

• Bass Bennett — reveals the larger hotel plan to him
• Cutler Heart — reveals the larger hotel plan to him

Briar's deceased mother, who had an affair with William Winchester. Her three letters reveal she told William she was pregnant with Briar, rejected his $5,000 check, refused his money for silence, and warned him to stop writing. She valued trust and integrity and raised Briar alone.

Arc: Through her letters, she posthumously exposes William's knowledge of Briar and gives Briar the leverage to reclaim her power and her family narrative.

• Briar Sinclair — daughter
• William Winchester — former affair partner and father of Briar
• Granny Sinclair — mother

Briar's roommate and close friend. After Briar's mother and grandmother died, Savannah took Briar home for Christmas, where her family gave Briar a 23andMe test. She wanted to give her grieving bestie the gift of genetics.

Arc: She remains a background but important friend from Briar's past who inadvertently helped Briar find her father's family.

• Briar Sinclair — roommate and close friend

Briar's grandmother, who raised Briar's mother as a single mother and was close to Briar. She was diagnosed with cancer, given three months to live, and died in her sleep six months after Briar's mother died. Briar believes she died of a broken heart.

Arc: She remains an important figure in Briar's past whose loss shaped Briar's fear of goodbyes.

• Briar Sinclair — granddaughter
• Josephine Sinclair — daughter

Tatum's stepsister, who died in a car accident before the present events. She had a five-year-old son named Oliver, whose father overdosed before Oliver was born. She used drugs before pregnancy, got clean, and hid Oliver from Tatum out of shame.

Arc: She is deceased but drives the late-story subplot through her will, which names Tatum as the person she wanted to care for Oliver.

• Tatum Monroe — stepsister
• Oliver — son
• Brenna — helped her through a program, housing, and a diner job
• Ricardo Wallis — attorney

Raelyn's five-year-old son, whose father overdosed before he was born. Raelyn was raising him alone and hid him from Tatum out of shame. Raelyn's will states that if anything happened to her, she wanted Oliver in Tatum's care.

Arc: He becomes the emotional center of Tatum and Phoenix's late-story subplot after Raelyn's death and will are revealed.

• Raelyn — mother
• Tatum Monroe — Raelyn wanted him in her care

Attorney handling Raelyn's will and husband of Brenna. He meets Tatum and Phoenix in his office, reveals that Raelyn had a son named Oliver, and explains Raelyn's history and will. He says the situation is complicated.

Arc: He delivers the news of Raelyn's son and will, setting up Tatum's potential custody of Oliver.

• Brenna — wife
• Raelyn — her attorney
• Tatum Monroe — meets with her about Raelyn's will
• Phoenix — meets with him and Tatum

Ricardo Wallis's wife who runs a program for women needing support and assistance. She found Raelyn housing and got her a job at the diner. She helped Raelyn when she was pregnant and during Oliver's first year.

Arc: She remains a background helper whose support shaped Raelyn's recovery and Oliver's early life.

• Ricardo Wallis — husband
• Raelyn — helped her through a program

Tatum's work contact whom she calls when she cannot work the next day. He lets her switch days that week. He is a minor figure in Tatum's life outside the friend group.

Arc: He remains a minor work contact who accommodates Tatum after Raelyn's death.

• Tatum Monroe — work contact she calls about switching days

Bass's ex-girlfriend who wanted marriage and gave him an ultimatum. They broke up last year, and she never showered on the houseboat. She is part of Bass's romantic past.

Arc: She remains a background figure whose relationship with Bass helps explain his guardedness about commitment.

• Bass Bennett — ex-girlfriend

Gracie and Cutler's bulldog, who is present when Briar trips near the container park and is helped by Gracie. Clover plays with him, and Bass gives him a leftover steak and beef bone.

Arc: He remains a friendly pet in the friend group, appearing during family and wedding-related moments.

• Gracie — owner
• Cutler Heart — owner
• Clover — plays with him
• Bass Bennett — gives him leftover steak

Gracie's mother, who watches emotionally as Gracie tries on and chooses her wedding dress. She is part of the bridal boutique scene.

Arc: She remains a minor family figure celebrating Gracie's wedding preparations.

• Gracie — mother

Cutler's mother, who watches emotionally as Gracie chooses her wedding dress. Cutler shares that his mother's cancer made him fear closeness, shaping his views on love and loss.

Arc: She remains a background figure whose illness influenced Cutler's emotional growth and his advice to Briar.

• Cutler Heart — son
• Gracie — future daughter-in-law

An old friend and business associate of William Winchester who offered the larger hotel idea to William. He is mentioned as the source of the K&R deal idea that threatens Blue Sky Bay.

Arc: He remains a minor off-page business contact whose idea drives the larger hotel conflict.

• William Winchester — old friend and business associate