Living in the vibrant city of Los Angeles, aspiring stand-up comedian and actress Andrea Singer finds herself grappling with the challenges of her chosen career. She feels a twinge of bitterness towards Serrena, a fellow performer who has eclipsed her in success despite sharing a similar journey. This sense of frustration intensifies during a chance encounter at the airport, where she meets Dennis Kelley. He comes to her aid by returning her misplaced boarding pass, setting their unexpected relationship into motion.
Seated next to Dennis on their flight back home, Andrea quickly learns that he is far more than he seems—a Yale graduate employed in the hedge fund sector. Their chemistry flourishes as they spend time together in the city, bonding over drinks at Margot's bar, Andrea's best friend. Intriguingly, Andrea finds Dennis to embody both pompousness and humility, a refreshing contrast to the typical personalities she encounters in her profession. Their friendship deepens, with Dennis supporting her through auditions, yet Andrea is adamant that her feelings for him are purely platonic.
However, everything shifts after a performance at The Comedy Store where Dennis unexpectedly proposes they become a couple during a lavish dinner marred by a declined credit card. His claims, such as having ordered a beautiful bracelet for her from Cartier, do little to sway Andrea, who remains unimpressed and uninterested.
The trajectory of Andrea’s acting career takes a dramatic turn when she lands the lead role in the series "Space Cadet," much to her joy. Eager to share this milestone, she reaches out to Dennis, who suggests they celebrate together. Unfortunately, Andrea already has plans with someone else. In an unexpected turn of events, Dennis disrupts her date under the guise of familial distress regarding his supposed dying mother, leading to an uninhibited night that culminates in their first kiss and an agreed-upon commitment.
As their relationship blossoms, Andrea and Margot grow increasingly suspicious of Dennis's claims, prompting them to investigate his background. Their inquiries lead them to an address that reveals Dennis's misleading claims about his living situation, including the shocking truth of his two female roommates.
Confronted with deceit, Andrea has an emotional showdown with Dennis, who continues to fabricate stories, insisting that his sick mother lives with him. In an effort to bolster their relationship, they spend a weekend with Andrea's cousin Brett and his partner, both successful Yale graduates. A round of golf intended as a bonding experience is thwarted when Dennis fakes an injury, raising further red flags for Andrea.
As doubts mount, Andrea seeks clarity concerning Dennis's credentials, which leads to an awkward moment when he presents her with a gaudy ring that he claims symbolizes their engagement. Just as Andrea is trying to sort out her feelings, her best friend Margot calls with more unsolicited dirt on Dennis, fueling Andrea's growing unease.
The tensions escalate when Serrena unexpectedly shows up during a pivotal table read, initially instigating anger in Andrea, but later coaxing her to dig deeper into Dennis's life alongside Margot. The supposed home of Dennis is revealed to be occupied by a Hispanic woman named Denise, and further inquiries from Andrea and Margot uncover the reality behind his dubious claims about work and education.
In a fit of vengeance and resolve, Margot gets Dennis intoxicated, leading to unintended injuries. This incident spirals out of control and culminates in Dennis taking Andrea to court for kidnapping, a move that thrusts their tumultuous saga into the public eye. Amidst all this chaos, Andrea is left with a restraining order against Dennis, providing her with new material for her stand-up routine and a painful comedic twist to her already complicated life.
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