As they approach the end of their 20s, two lifelong friends, Paige, an environmental lawyer, and Sasha, a struggling musician turned receptionist, embark on a journey through the often complex and unpredictable world of relationships. Paige's steadfast support for her lesbian friend is matched only by their shared love for cozy evenings filled with TV shows. However, when they decide to take a leap into the realm of online dating, the course of their lives changes dramatically. While Sasha finds herself facing a series of disappointing dates, Paige unexpectedly falls for Tim, a charming and dashing dermatologist whose thoughtful gestures capture her heart.
As Paige's relationship with Tim flourishes, she faces the delightful yet challenging role of balancing her mother's matchmaking suggestions while navigating her own emotions. Tim's thoughtful nature impresses Paige’s mother as she encourages him to refine his style. Yet, Sasha begins to feel sidelined as Paige’s attention shifts from their longstanding friendship toward her relationship. The tension increases on Sasha's significant 29th birthday, when a surprise celebration at a motel is interrupted by a call from Tim, throwing a wrench into the festivities and marking a pivotal moment in their friendship.
As the dynamics become more strained, Paige begins to view Sasha through a different lens, growing frustrated with her friend’s lack of direction and seemingly poor choices in romantic partners. This growing concern from Paige clashes with Sasha’s feelings of exclusion and undervaluation. Things come to a head when Sasha's latest girlfriend, who has a complicated history with one of their mutual friends, is met with resistance from their circle.
Anticipating a summer barbecue, Paige and Tim hope to repair the rift by introducing Sasha to a compassionate lawyer from her firm. Yet, when Sasha dismisses the new acquaintance, Paige’s frustrations erupt, leading to a confrontation that threatens their once-solid friendship. Simultaneously, Sasha faces the consequences of her actions as she experiences the harsh reality of job loss after failing to secure a crucial bid for her company's venture in China. This setback serves as a stark reminder of the dangers of complacency in one’s career.
Meanwhile, as Tim grapples with Paige's increasing need for control in their relationship, a poignant conversation leads him to gently guide Sasha to reconsider her musical aspirations. This heartwarming exchange opens Sasha's eyes to new possibilities, highlighting Tim's kindness at a time when she needs it most.
In the midst of her struggles, Paige has an epiphany while spending an afternoon at a bridal shop with her overbearing mother, as she fights to find the perfect dress among a sea of fabric. It's during this moment of reflection that she begins to understand her insecurities and the role they play in her life. This newfound awareness ultimately leads to a heartfelt apology to Tim, marking a significant step towards accountability and growth, while illustrating the healing power of vulnerability in relationships.
The story arrives at a touching climax when Sasha and Paige meet at a traffic light, allowing them a moment to reconnect. In a playful exchange of mock indignation, they share a nostalgic game that encapsulates their renewed bond, illustrating that, despite the challenges they've faced, their friendship endures with resilience and warmth.