Kate can’t stop thinking about her kiss with Callum. On the train, her mother, Delilah, finds her deep in thought and senses something’s weighing on her.
Meanwhile, Callum is just as distracted. He starts to text Kate but hesitates right as Oliver shows up.
Kate finally confides in her mom, admitting that Callum kissed her and she hasn’t heard from him since. She’s confused about what it means.
Oliver apologizes to Callum for everything that happened with Sara, but Callum brushes it off and vents about another woman. Oliver, relieved that it’s not about Sara, encourages him to tell this mystery woman how he really feels.
Back with Kate, Delilah gives her signature brand of questionable advice: don’t shy away from the mess. She even suggests finding a third man to gain perspective.
Later, Delilah turns her focus toward helping Kate professionally. She turns on the charm with Kate’s boss, dropping subtle compliments to keep Kate in good standing at work.
Just as Kate starts to find her footing again, she gets a text from the 12 Dates host that her next date is in an hour.
At The Pear Tree, Mac is pleasantly surprised to see Evelyn. She’s polite but distant, still not ready to be friendly with him again.
Kate meets her new date and conversation flows easily. But things take a turn when she spots Richard on a date with another 12 Dates participant. Caught off guard, Kate’s jealousy shows. Richard calls her out for it.
Elsewhere, Delilah corners Evelyn to ask what her intentions are toward Mac. She urges her to go for it, but Evelyn brushes it off, claiming she’s not interested.
Laura arrives at the café and shares that she’s just been promoted to partner at her law firm but she’s not sure how she feels about it. Delilah, on a roll, tells her she’s been helping everyone with their love lives, Evelyn with Mac, and Kate with Callum. Realizing she’s said too much, she abruptly stops herself. Laura catches the slip and presses for details, but Delilah flees before she can say more.
Back at the date, Kate’s companion picks up on her interest in Richard and offers to help.
Meanwhile, Delilah seeks out Mac for damage control. He’s not surprised she’s put her foot in her mouth again. To distract her, she convinces him to take her for a bike ride. When Evelyn spots them together, she’s quietly miffed.
Kate’s date takes her to a design exhibit, where they bond over creativity and aesthetics. As they discuss textile patterns, Kate admits she likes “making order out of chaos.” When he mentions he’s leaving the country soon, she realizes he’s not looking for anything serious.
Elsewhere, Mac grows irritated when Delilah mentions how upset Evelyn looked seeing them ride past. He snaps that Evelyn probably thinks they’re together and rushes off to fix it.
He finds Evelyn mid-dance class and blurts out that there’s nothing going on between him and Delilah. He asks her out, but Evelyn scoffs at the idea.
Meanwhile, Callum shows up at Laura’s kid’s school play, looking for Kate. When he finds her, he admits he wants her to take him seriously. Laura’s eyes widen as she had no idea they kissed. Kate, unsure what to think, wonders aloud if she’s just a rebound.
At The Pear Tree, Callum crosses paths with Evelyn again and urges her to give Mac a chance before it’s too late. She pointedly asks if that’s what happened between him and Kate.
Delilah later apologizes to Kate for spilling information about her and Callum. To her surprise, Kate takes it well and even admits that her mom’s earlier advice helped.
Laura, still reeling, goes to talk to Callum about Kate. He tells her everything about what happened years ago and what happened recently. Laura offers to help patch things up, but Callum doubts it will make a difference. She insists it’s not too late.
Evelyn, finally ready to face her feelings, visits Mac. She admits she never imagined being with anyone after her husband’s death but she can’t deny she feels something for him. Mac is stunned, then elated. She agrees to go on a date, and they share a kiss.
Across town, Kate’s professional life gets an unexpected boost. Her boss tells her that The Winterhorn gallery wants to feature one of her designs in their exhibit celebrating influential British designers and it’s one of Kate’s pieces.
For Date #11, Callum and Laura secretly team up with Drew to plan the perfect evening for Kate. But something goes wrong. Instead of showing up at Callum’s carefully arranged location, Kate ends up somewhere else, with Richard.
Callum, waiting at his setup, is left disappointed.
Kate, however, is taken aback by the beautiful atmosphere Richard has planned. He confesses he never expected the 12 Dates experiment to actually work but meeting her changed that. She’s touched by his sincerity.
Later that night, Laura confides in her husband that she feels awful about meddling in everyone’s lives. She promises to stop interfering and admits she’s ready to quit the firm altogether.
At the same time, Kate and Richard enjoy their evening, talking easily and reconnecting over shared laughs and memories.
Elsewhere, Mac psychs himself up for his long-awaited date with Evelyn. But just as he’s getting ready, he suddenly collapses at home.
Moments later, Kate’s phone rings. It’s Callum. Her heart sinks as he tells her that her father’s in the hospital. Kate and Richard drop everything and rush out.