Before marrying Saira Banu, Dilip Kumar was deeply in love with Madhubala. Their romance began while filming Tarana, and they even considered marriage. However, Madhubala’s father disapproved, leading to their breakup during the making of

Mughal-e-Azam

.
Despite this, they shared a unique bond. Dilip Kumar recalled Madhubala wanting to meet him soon after his marriage to Saira Banu.
In his autobiography The Substance and the Shadow, Dilip Kumar shared an instance where Madhubala wanted to meet him after his marriage to Saira Banu. When he informed Saira about it, she encouraged him to meet Madhubala without hesitation. Dilip admired Saira’s maturity and her ability to focus on the present rather than the past.
He detailed the incident and wrote, “Soon after our nikah (marriage), while we were staying in Madras, I received a message from Madhubala that she wished to see me urgently. I confided in Saira as soon as we returned to Bombay about the message. Saira at once insisted that I should meet Madhu since it must be something she was distressed about.”

Dilip further recalled visiting Madhubala at her home and described her frail and weak appearance. He noted that her radiant smile seemed forced due to her ill health. Despite this, Madhubala expressed her happiness for him, saying, “Hamare shehzade ko unki shehzadi mil gayi hai, main bahut khush hoon!” (Our prince has found his princess; I am very happy).

Dilip Kumar recalled that during their final meeting, Madhubala sought his advice on personal issues troubling her. They discussed her concerns until she felt somewhat reassured. Reflecting on this poignant moment, he wrote, “That was the last time I saw her. She passed away on 23 February 1969.”
Madhubala married Kishore Kumar in 1960, but their marriage faced challenges and was far from smooth. Tragically, nine years later, the iconic actress passed away due to a heart attack at just 36 years old.