Married twice, thrice, even four times! Bollywood’s most scandalous love lives

Bollywood love stories often grab as much attention as films. While some actors find their soulmate once and stay happily married, others go through more than one marriage in search of lasting companionship. From legendary stars like Dilip Kumar and Kishore Kumar to modern names like Saif Ali Khan and Karan Singh Grover, the list of Bollywood actors with multiple marriages is long and fascinating. Here’s a look at some of the most well-known names and the history behind their marriages.

Dharmendra: Prakash Kaur and Hema Malini

The “He-Man of Bollywood,” Dharmendra, first tied the knot with Prakash Kaur before entering the film industry. Later, his on-screen chemistry with Hema Malini turned into real-life romance. To marry Hema without divorcing Prakash, Dharmendra reportedly converted to Islam in 1980. Since then, both marriages have continued, with Dharmendra sharing his life between two families.

Raj Babbar: Nadira Babbar and Smita Patil

Actor-politician Raj Babbar was married to theatre personality Nadira Babbar when he fell in love with actress Smita Patil. He married Smita, and the two had a son, actor Prateik Babbar. However, tragedy struck when Smita passed away shortly after childbirth in 1986. Following her death, Raj eventually reconciled with Nadira, and the couple continued their journey together.

Kishore Kumar: Four Marriages, Four Stories

The legendary singer-actor Kishore Kumar was known as much for his eccentric personality as his melodious voice. He married four times: first to Ruma Guha Thakurta, then to actress Madhubala (a love story still remembered fondly), followed by Yogita Bali, and finally Leena Chandavarkar. Each marriage carried its own share of drama, heartbreak, and emotional complexity, but Kishore’s charm remained unmatched.

Karan Singh Grover: From Shraddha to Bipasha

Television star-turned-Bollywood actor Karan Singh Grover has also had multiple marriages. He first married Shraddha Nigam, but the marriage ended quickly. Later, he married popular TV actress Jennifer Winget, though that too didn’t last long. In 2016, he found love again with actress Bipasha Basu, and the couple has since been inseparable, often seen sharing glimpses of their family life with baby Devi on social media.

Dilip Kumar: Saira Banu and Asma Rehman

The late Dilip Kumar, often called the “Tragedy King” of Bollywood, had a complex personal life. He was briefly married to Asma Rehman in the early 1980s, but the relationship didn’t last long. Eventually, his lifelong love story began with actress Saira Banu, whom he married in 1966. Despite the 22-year age gap, their marriage stood the test of time and remained one of Bollywood’s most cherished unions until his passing.

Boney Kapoor: Mona Kapoor and Sridevi

Producer Boney Kapoor was first married to Mona Shourie Kapoor, with whom he had two children, Arjun and Anshula Kapoor. However, his love for actress Sridevi changed the course of his life. He married Sridevi in 1996, and the two remained together until her untimely passing in 2018. The marriage was one of the most talked-about unions in Bollywood history.

Sanjay Dutt: Richa Sharma, Rhea Pillai, and Manyata Dutt

Sanjay Dutt’s personal life has been filled with ups and downs. His first wife, actress Richa Sharma, passed away due to cancer. Later, he married model Rhea Pillai, but their marriage ended in divorce. In 2008, Sanjay tied the knot with Manyata Dutt (formerly Dilnawaz Shaikh), and the two are still together, raising their twins, Shahraan and Iqra.

Kamal Haasan: Vani Ganapathy and Sarika

Although more associated with Tamil cinema, Kamal Haasan’s connection to Bollywood cannot be ignored. He first married dancer Vani Ganapathy, but the marriage ended in divorce. Later, he married actress Sarika, with whom he has two daughters, Shruti Haasan and Akshara Haasan. After their split, Kamal lived in a long-term relationship with actress Gautami, though they eventually parted ways as well.

Naga Chaitanya: Samantha and Sobhita Dhulipala

Actor Naga Chaitanya, known for his Telugu films but also tied to Bollywood circles through family, married actress Samantha Ruth Prabhu in 2017. However, the couple divorced in 2021, shocking fans. Post-divorce, Chaitanya got married to Sobhita Dhulipala in an intimate ceremony.

Aamir Khan: Reena Dutta and Kiran Rao

Bollywood superstar Aamir Khan married Reena Dutta in 1986, and the two shared a long marriage before parting ways in 2002. In 2005, he married filmmaker Kiran Rao. Their marriage lasted 15 years, and they continue to co-parent their son Azad even after announcing their separation in 2021. Now Aamir Khan is dating Gauri Spratt and is often seen making a presence with her.

Saif Ali Khan: Amrita Singh and Kareena Kapoor Khan

The Nawab of Pataudi, Saif Ali Khan, married actress Amrita Singh in 1991, and they had two children, Sara and Ibrahim. The couple divorced in 2004. Years later, Saif married Kareena Kapoor in 2012, and together they have two sons, Taimur and Jeh. Saif and Kareena remain one of Bollywood’s most high-profile couples today.

From Dilip Kumar’s lasting bond with Saira Banu to Saif Ali Khan’s glamorous second marriage with Kareena Kapoor, these stories reveal how love in Bollywood can be both fragile and enduring. For many of these stars, multiple marriages were simply different chapters in their search for companionship and happiness.