Lucy Mason, a former actress, works as a successful
matchmaker at Adore in New York City. She expresses cynicism about her own romantic prospects while growing frustrated with her clients' unrealistic standards. Her long-term client Sophie is struggling to lower her standards and settle while Lucy consoles her over her recent rejection. Lucy attends a former client's wedding, the ninth she has been responsible for. The bride is crying, feeling she is marrying for shallow reasons and out of obligation, but Lucy ultimately persuades her to proceed with the ceremony. At the wedding reception, Lucy is approached by
financier Harry Castillo, the groom's brother, who overhears Lucy's business pitch to other singles at the party. He shows interest in her, but she rebuffs him, suggesting instead that he become an Adore client. Also at the wedding is Lucy's ex-boyfriend John Pitts, who is working as a cater-waiter and continues to pursue acting. They reminisce about their past relationship, which ended due to differing financial aspirations. Harry persists in courting Lucy, taking her to upscale restaurants. She initially questions his interest, believing he could find a better partner, but he reassures her that his interest is genuine. Their relationship becomes official, and Lucy's renewed optimism translates to her work life; Sophie's latest match Mark tells Lucy that he enjoyed the date with Sophie and wants to see her again. Lucy's confidence is shaken when her boss, Violet, informs her that Sophie is suing Adore because Mark assaulted her after the date. Violet tells Lucy that the situation was out of her hands, orders her to take four weeks off to clear her mind and instructs her not to contact Sophie due to the lawsuit. Despite Violet's warning, Lucy tracks Sophie down and personally apologizes. Sophie angrily rejects the apology, calling her a "pimp" who was looking to pawn off a problem client on any man she could, regardless of the consequences. She storms off, adding to Lucy's guilt. Preparing to travel to Iceland with Harry, Lucy finds an engagement ring in his luggage. Later that night, she discovers he had undergone a $200,000
tibial lengthening surgery to increase his height. He defends the decision, asking her if it changes her feelings for him. While it does not, Lucy realizes they are both pursuing the relationship simply because they "check the boxes" of what each is seeking in a partner, but are not actually in love. They amicably break up. As Lucy had
sublet her apartment because of the trip, she visits John, who suggests they travel
upstate with money he earned from his play. At a wedding they
gatecrash together, she kisses him. When John asks if they are getting back together, Lucy expresses uncertainty, citing her conflicted values. John confesses he has always loved her and envisions a future together despite his insecurity for not being able to provide the relationship she wanted, while Lucy admits that her dissatisfaction with John's financial situation overshadowed their love when they were together and assumes that John hates her, which he denies. Lucy receives a panicked call from Sophie; Mark is outside her apartment and the police are refusing to intervene since he has not broken in. Lucy and John rush back to the city, finding that Mark has already left. Lucy helps Sophie file a restraining order and they reconcile. Before parting, John appeals to Lucy to rekindle their relationship, promising to remind himself every day that he loves her and work harder to support their relationship. Later, it is revealed through a phone call from Violet that Sophie begins dating a new match from Adore; Harry has also become a client. Violet, who is needed to handle another branch in London, offers Lucy a promotion to lead the New York office. Lucy reveals that she intended to resign but agrees to consider the offer. In
Central Park, John proposes with a flower ring, and Lucy accepts. The credits depict various couples, including Lucy and John, receiving marriage licenses at the city clerk's office. == Cast ==