Khaitan made his directional debut with the romantic comedy
Humpty Sharma Ki Dulhania. His initial plan with
Humpty Sharma Ki Dulhania was to make it a story of two con artists, similar to
Bunty Aur Babli, but the script eventually became a story of a flirtatious Punjabi boy who engages in a romantic affair with an engaged Punjabi woman once he found the characters turning sweeter and falling in love. After finishing the first draft of his script, then with the title
Humpty Sharma Di Love Story, Khaitan sent it to
Dharma Productions, wherein producer
Karan Johar approved its production with a first time writer-director at the helm, breaking a legacy norm at the company wherein most debutante directors had previously served as assistant and/or associate directors in the company's films. Khaitan cited
Dilwale Dulhania Le Jayenge (DDLJ) and
Casablanca as inspiration for his script, and the film itself pays homage to
DDLJ as well as
Kuch Kuch Hota Hai. Khaitan's next venture was the romantic comedy
Badrinath Ki Dulhania (2017)which reunited him with Bhatt and Dhawan. It tells the story of an independent young woman (Bhatt) who refuses to conform to patriarchal expectations from her chauvinistic fiancée (Dhawan). Rachel Saltz of
The New York Times took note of the film's statement on gender equality. The film proved to be commercial successes, earning over at the box office. It earned him a nomination for the
Filmfare Award for Best Director. Khaitan had begun co-writing the script for the Hindi adaptation of
John Green's 2012 novel
The Fault in Our Stars with the intent to direct it for Dharma Productions with
Janhvi Kapoor and
Ishaan Khatter as leads in 2017. However, after Dharma opted out, he eventually went on to direct them instead in
Dhadak, a remake of the
Marathi film
Sairat (2016) which released the following year. While
Dhadak received negative reviews from film critics for glossing over the subject of
caste-based discrimination and for being a poor remake of the original, it emerged as a commercial success with worldwide earnings of over . Khaitan later turned an independent producer for Dharma Productions with the comedy
Good Newwz (2019), which emerged as one of
highest-grossing Bollywood film of 2019 and the horror thriller
Bhoot – Part One: The Haunted Ship (2020), the first installment of a planned horror franchise which ultimately did not expand as of 2025. His adaptation of
The Fault in Our Stars was finally released under the title
Dil Bechara the same year. The following year, he wrote and directed a segment titled
Majnu in the Netflix
anthology Ajeeb Daastaans. He was to direct Dhawan and Kapoor again alongside Bhumi Pednekar in what was touted to be the spy thriller
Mr. Lele, but the project was indefinitely postponed in light of the
COVID-19 pandemic, and he later reportedly revived it as a comedy thriller titled
Govinda Naam Mera (2022); starring
Vicky Kaushal as the titular character instead of Dhawan,
Kiara Advani instead of Kapoor, and Pednekar, it was streamed on
Disney+ Hotstar. Khaitan next wrote the story and screenplay for Johar's comeback film as director, the romantic comedy drama
Rocky Aur Rani Kii Prem Kahaani (2023), starring
Ranveer Singh and Bhatt, with Dhawan making a cameo appearance in a song. The following year, he produced his first collaboration with Dhawan's and Bhatt's fellow debutante
Sidharth Malhotra, the action thriller
Yodha, under Mentor Disciple Entertainment alongside Johar. His next film as writer, producer and director,
Bedhadak, was also announced,{{Cite news|date=|title=Bedhadak: Karan Johar shares posters, announces Shanaya Kapoor's debut movie with Lakshya and Gurfateh Pirzada == Filmography ==