The Last Kiss 2006

As the pregnancy test yields a positive result, Michael (Zach Braff), a 29-year-old man, and his live-in girlfriend Jenna (Jacinda Barrett) seem to have it all - a loving relationship that is ripe with affection. Her stunning physical attributes aside, Jenna’s parents are now breathing down their necks to tie the knot, citing the impending arrival of their grandchild as reason enough for Michael and Jenna to take the plunge. However, Jenna insists that the timing isn’t right due to her own academic pursuits and Michael’s demanding work schedule - unaware that her partner is secretly harboring doubts about their future together.

Meanwhile, Michael’s friends are facing their own marital woes: Izzy is reeling from a toxic break-up with Arianna (Marley Shelton), who has left him feeling drained; Chris, on the other hand, is struggling to navigate his relationship with Lisa (Lauren Lee Smith) after she reveals her deep-seated mistrust of him. As Michael confides in his friends about his own concerns, he begins to realize that all marriages aren’t created equal.

At a wedding, Michael meets Kim (Rachel Bilson), a vibrant and carefree individual who senses his turmoil and offers words of encouragement. Though Michael is initially drawn to her youthful energy, he resists the temptation to rekindle an old flame, choosing instead to prioritize his relationship with Jenna. Little does he know that Kim has taken note of his inner conflict and will later offer him a glimpse into her own life at the University of Wisconsin-Madison.

As tensions within the couple continue to simmer, Michael’s anxiety reaches a boiling point when Jenna proposes they buy a house - with her parents’ help, no less. Feeling suffocated by the prospect of settling down, Michael demands that Jenna prove their love is built to last by pointing out three long-lasting couples. Jenna, unaware of the underlying issues, cites her own parents as the perfect example - oblivious to the fact that they too are struggling with marital discord.

Jenna’s mother, Anna (Blythe Danner), meanwhile, has grown tired of her husband Stephen’s affections and begins to secretly meet Professor Bowler (Harold Ramis), a man who has captured her heart. When she finally works up the courage to reveal her true feelings to her husband, it sets off a chain reaction that ultimately exposes the cracks in their seemingly idyllic marriage - leaving Jenna to wonder if her own relationship is equally doomed.

As Michael’s professional obligations take him to the Memorial Union, he finds himself coincidentally running into Kim, sparking a palpable chemistry that neither can ignore. Despite his initial attempts to downplay their encounter, Kim senses the sincerity behind his gaze and extends an invitation to join her at a party, which Michael readily accepts. Back in the office, Michael concocts a flimsy excuse to extricate himself from Jenna’s presence that evening, pleading a prior commitment that he hopes will stave off any potential meddling from Chris (Casey Affleck), his coworker and friend.

Chris is privy to Michael’s scheme but chooses not to intervene, aware that the perils of heartbreak are all too real after having recently parted ways with his wife. Though Michael assures him that his intentions are pure, Chris remains skeptical, knowing that the allure of a new connection can be potent. As the night wears on and Michael finds himself swept up in Kim’s charming company, he is drawn to her radiant energy, which leaves him feeling rejuvenated.

Their intimate moments are punctuated by invitations to spend more time together, but Michael’s lingering guilt over his unfaithfulness to Jenna ultimately prevails. His resolve is tested when tragedy strikes, as news of Izzy’s (Michael Weston) father’s passing brings the community together in condolence. Amidst this somber backdrop, Jenna’s suspicions about Michael’s nocturnal activities are piqued, thanks to Chris’s taciturnity and her own keen intuition.

When Michael finally returns home, he is met with a storm of anger from Jenna, who confronts him about his supposed evening spent with Chris. Initially evasive, Michael eventually confesses to having encountered someone else, though he emphasizes that no physical transgression occurred and the encounter held little significance. However, Jenna’s ire is too great, and she banishes Michael from her presence, threatening him with a culinary implement.

Left to grapple with his feelings of despair and desperation, Michael receives a call from Kim, who apologizes for any earlier demands and invites him over for a conversation. Though hesitant at first, Michael agrees, only to find himself succumbing to the allure of Kim’s presence. The next morning, he attempts to slip away without disturbing her but is forced to return after realizing his keys remain behind. Kim’s ire is piqued by his hasty departure, and she demands an explanation. Michael assures her that he did not wish to disturb her, given his early work commitments. Kim then retrieves the misplaced keys from her pocket and hands them back to him, provided he agrees to maintain contact with her.

As Anna finds common ground with Stephen and returns to their shared living space, the arrival of Jenna marks a new turning point in this complex web of relationships. Meanwhile, at his workplace, Michael contemplates making an early exit to track down Jenna, only to be unexpectedly visited by Kim, bearing a thoughtful mix CD as a gesture of goodwill. Seizing the opportunity, Michael shares his lingering feelings for Jenna with Kim, revealing that she is expecting his child and apologizes for not being more forthcoming earlier. With a heavy heart, he departs Kim’s presence, driven by a newfound sense of urgency to reconnect with Jenna.

Michael’s quest for forgiveness takes him to Jenna’s childhood home, where her father, Stephen (Tom Wilkinson), provides a stern but sage counsel on the importance of commitment and personal growth. He implores Michael to be completely truthful and never abandon his pursuit of reconciliation. Emboldened by this wisdom, Michael approaches Jenna’s room, only to be confronted with a crucial question about his honesty regarding his encounter with Kim. Though initially hesitant, Michael confesses that while his earlier declaration was technically true at the time, he had indeed returned to Kim later that night. Despite his impassioned pleas for understanding, Jenna’s outrage and hurt prove overwhelming, prompting her to storm out of the house and back to their apartment.

As Chris renews his connection with Lisa, Michael becomes determined to follow Jenna’s path, even if it means locking himself out of their home. Undeterred by the elements or the passage of time, he remains steadfastly posted on the front porch, earning both curious glances from neighbors and thoughtful gestures in the form of beverages. Even Stephen drives by, noticing Michael’s unwavering dedication to his cause, which inspires a proud smile as he disappears into the night.

As the days blend together, Jenna begins to soften her stance, initially by dispatching a blanket during an evening chill, then following up with a sandwich delivery the next day. It is on the third evening of his vigil that Jenna finally breaks her silence, speaking to Michael through the closed door in a poignant comparison between their “last romantic kiss” and the passing of her grandmother. The pain and longing are palpable as she mourns the loss of their relationship, much like one would mourn the loss of a loved one’s life.

Later that evening, as the stars align in his favor, Jenna opens the door to Michael’s persistent presence, allowing him to finally step inside and begin the arduous journey toward healing and reconciliation.