His involvement with Karisma began while shooting with her for Dharmesh Darshan's Haan Maine Bhi Pyaar Kiya. The romance that blossomed culminated in a formal announcement of their engagement at the JW Marriott, timed to coincide with dad Amitabh's 60th birthday celebrations.
"What better gift to my son than this engagement announcement?" Amitabh told rediff.com in 2002.
"She is my bahu and part of our home. I am very happy for Abhishek and Lolo (Karisma)," the Big B said.
And then things went sour, though none of the involved parties has ever spoken candidly about how, or why.
It was Neetu Singh, Rishi Kapoor's wife and Karisma's aunt by marriage, who dropped the bombshell in January 2003, when she told a newspaper that the engagement was off.
"I know it is off but I don't know the reason," said Singh.
The void left by the reluctance of the principals to speak to the record was filled with rumours. Karisma and her prospective mother in law Jaya Bachchan had, to put it mildly, failed to see eye to eye during the shooting of film critic-turned-director Khalid Mohammad's Fiza, was one explanation.
Others said Karisma's mother Babita did not take kindly to the Bachchans indicating that Karisma should not work after marriage. The edict, Babita supposedly felt, was a bit unfair, since her daughter was at the time flying high, while Abhishek's career seemed one flop away from self-destructing.
Don't Miss: Congratulate Ash, Abhishek