Mandar Ponkshe Gulshan Devaiah and his cousin, Dilip "Yusuf" Ponkshe Sagar Deshmukh, are introduced to sex and relationships by their older cousin, Kshitij Vaibhav Tatwawadi during a carefree summer visit. Back at school, Mandar asks out his first girlfriend, and his early swagger earns him the admiration of friends who look up to him for his smooth moves with women. Six years slip by before a misstep changes everything: Mandar is expelled from his college dormitory for bringing a girl to his room, and he relocates to a new apartment complex where he reconnects with his steady girlfriend, Parul. Yet a tempting sight—the attractive Jyotsna Surve Sai Tamhankar—draws him into an extramarital affair. Parul, feeling sidelined, bids him farewell, and the affair ends when Jyotsna’s husband confronts Mandar.
Meanwhile, Kshitij has grown into a polished military officer who appears to collect girlfriends as casually as his uniform. He still brings his conquests home to Mandar’s place, and in the course of these soirées, he learns of a woman named Anju, a survivor of sexual abuse at her father’s hands, through one of his girlfriends who knows Anju. Kshitij rescues and brings Anju home, a move that prompts Mandar and Yusuf to share a flippant, racist joke. Eventually, Kshitij and Anju marry and have a son, though Kshitij departs on military duty a while later, leaving Mandar to navigate life without his older cousin’s constant presence.
Over the next decade, Mandar hones his talent for attracting women but also tastes failure. He confesses to Yusuf that he someday wants to settle down, and he dives into matrimonial websites to seek an arranged marriage. His first couple of meetings collapse because his past conquests don’t sit well with conservative families. Taking Yusuf’s advice, he tries to present himself as demure and conservative to the next prospect, Tripti Radhika Apte, only to discover that she is liberal and rejects him for his image. Undeterred, he keeps pursuing, and Tripti’s openness hints at the possibility of a change of heart.
Tragedy strikes when Kshitij is killed during an encounter in Kashmir. Mandar is crushed by the loss, and in the wake of his grief, Tripti grows closer to him. The two become engaged, and at a pre-wedding party Mandar meets Tripti’s former boyfriend, Chaxx Suraj Jagan, a sight that unsettles him. Tripti clarifies that Chaxx is in the past and she intends to build a present and future with Mandar. Although Mandar and Tripti have not yet had sex, a last fling with a former flame leads Mandar to a hotel—only for the encounter to end in embarrassment when the woman turns out to be a distant relative. He returns to Tripti the next morning and begins to tell the truth.
At Tripti’s house, Chaxx is sleeping on the couch, and Tripti makes it clear he is merely visiting. Mandar admits he lied about his past to win a partner for marriage, expecting Tripti to call off the wedding, but she finds comfort in his honesty and reveals that Chaxx is a thing of the past; she plans to build a present and future with Mandar. The couple share a kiss, and Mandar feels he has finally laid his demons to rest after a life spent pursuing women. He later hails a ride with Yusuf in an auto rickshaw, recounting two versions of the same story and ultimately confirming that the second version—his honest account without the deceptions—is the true one.
