On the cusp of turning 40, a newly-single Whitney finds herself stuck on the sidelines, watching as her friends celebrate life's most joyous milestones. With no time to waste, Whitney must decide what she wants her next chapter to look like.
Whitney seeks comfort from heartache by spending Thanksgiving with her Alabama family, but when they invite a potential love interest for her she worries if she'll crumble under the pressure.
Back from Kentucky, Whitney faces Kenny's shocking revelation, resetting her dating journey; meanwhile, Hunter's movie premiere with his family and a new date may suggest a more serious romance tham others suspected.
On the one-year anniversary of her mother's passing and with Christmas quickly approaching, Whitney works to recreate the holiday magic Babs used to make by throwing a legendary holiday party.
Whitney sets new goals to get over grief and find love again, but when the planning for her niece Jamie's bachelorette party takes over, her resolutions are pushed aside, and an unexpected party crasher threatens to throw everything into chaos.
Whitney, Angie and the bachelorettes get a wild lesson in intimacy, making Jaime uncomfortable; Whitney reflects on her life, questioning her past choices and her dating future and faces challenges regarding her fertility.
With her 40th birthday approaching, Whitney watches as her friends get married and have babies; determined not to be left behind; Whitney attempts to quell this mid-life crisis with the help of non-traditional alternatives.
Whitney's matchmaker pushes her to meet men in person; though she finds someone interesting, her confidence wavers; Glenn remains stubborn about home renovations, delaying necessary changes.
Whitney seeks Flamenco inspiration for her Spain trip ahead of her 40th birthday; with Jaime and Heath's wedding approaching, Whitney fears a confrontation with Kenny.
As Whitney prepares for her 40th birthday trip to Spain, tensions rise as Glenn pushes a wedding engagement on Hunter; Tal reveals he may not be able to join Whitney as he checked himself into mental health treatment.
Whitney kicks off her 40th birthday trip to Spain, but bad weather and Todd's gloomy attitude immediately derail the plans. Whitney takes a bold step to land a date with a Spanish hunk.
After Juan's rejection, a witch offers to fix Whitney's cursed love life; as the joint 40th birthday nears, Whitney fears Todd will be a no-show for their Flamenco performance, and Glenn amps up the pressure on Hunter to propose.
