Lucy, Monica Potter, is a journalist who is dumped by her seemingly perfect boyfriend and decides to test her heart with a year-long dating experiment. Across five distinct months, she meets five very different men, each encounter revealing a new facet of her own desires and boundaries.
In January, she dates John Hannah as Doug, an entomologist. The first meeting is light and flirty, but Lucy finds herself more unsettled than she expects, and the night ends with Lucy a little ungrounded and Doug trying to loosen up as the date progresses. The experience nudges her toward openness, even if the connection isn’t exactly what she is seeking.
Come May, Lucy meets Gael García Bernal as Gabriel, a successful playwright. What begins as a promising spark gradually reveals that Gabriel isn’t the right fit for her life plan. The encounter evolves into a one-night stand that leaves Lucy reflecting on what she truly wants from a partner, rather than simply chasing chemistry.
In July, her date is with Anthony LaPaglia as Bobby, a former baseball player with a big heart but out of his element in unfamiliar social settings. Lucy pushes him toward new experiences, and he leads her to a baseball card show where she witnesses a warmer, more vulnerable side of him. The day-to-day differences between them illuminate what each of them brings to a relationship, steering Lucy toward a more honest assessment of compatibility.
September brings Henry Thomas as Barry, a computer store owner who proves to be unexpectedly attentive. Their date starts rocky but gradually softens as Barry shows thoughtfulness and genuine care. He brings small, meaningful gestures into the mix, catching Lucy off guard and gradually winning her over with his steady, steady kindness.
The year comes full circle in December with David Boreanaz as Luke, an orthopedic doctor. Their connection grows more serious, yet an awkward restaurant moment where Luke is rude to a waiter unsettles Lucy and makes her question whether he aligns with her values and expectations. The scene is a turning point that helps Lucy recognize the kind of partner she truly wants.
As the year unfolds, Lucy and her dates navigate the complexities of rebound feelings, personal growth, and the evolving idea of what companionship really means. Lucy herself stays observant, choosing moments that push her toward a clearer sense of who complements her life. On Luke’s side, a chance encounter with a colleague and his daughter, Eve, Julie Gonzalo adds another layer to the story, highlighting how other people can influence one’s own choices. Eve’s presence hints at the ways attraction and connection can appear in unexpected places.
Across all five dates, Lucy is forced to examine what she wants more deeply: the excitement of new romance, or the stability, respect, and genuine care that come from knowing someone well. In the end, the film suggests that the best match for Lucy is not defined by a single ideal, but by the combination of affection, authenticity, and thoughtful acts that prove a relationship can withstand the tests of time and self-discovery. The journey is funny, tender, and oddly hopeful, underscoring that growth often comes through trial, conversation, and the willingness to choose someone who truly resonates with who you are becoming.
