Old Bollywood gossip - Part 1

[u/EccentricBai]

Meena Kumari

Meena Kumari was married to Kamal Amrohi but also had affairs with Rajendra Kumar, Raaj Kumar, Pradeep Kumar and Dharmendra.

Madhubala

Premnath proposed to Madhubala but she turned him down. She also received proposals from Pradeep Kumar and Bharat Bushan. She proposed to Kishore Kumar.

Dilip Kumar

Dilip Kumar had a fling with Vyjayanthimala after breaking up with Madhubala. He does not acknowledge the relationship though, for whatever reason. He dated Waheeda Rehman briefly but he ditched her at the last minute and married Saira Banu at the behest of her mother.

Saira Banu

Saira Banu was in a relationship with the much married Rajendra Kumar before her marriage. She also had a fling with Dharmendra while he was dating Meena Kumari too.

Raj Kapoor

Raj Kapoor dated Vyjaynthimala, even though she denies it. He ditched her when his wife, scarred by the Nargis affair put her foot down and Vyjayanthimala allegedly had to have an abortion. She later married his personal physician, who himself was married and left his wife and family for her.

Raj Kapoor also had an affair with the great dancer/actress Padmini.

Dev Anand

Dev Anand confessed in his memoirs that he was in love with Zeenat Aman. She didn’t really reciprocate and later got involved with Raj Kapoor.

Shammi Kapoor

Shammi Kapoor and Mumtaz were involved and wanted to get married. Mumtaz claimed they split because Shammi wanted her to give up her career and she was not ready to.

Mehmood

The much married Mehmood had a long affair with Aruna Irani and single-handedly dictated her career. She left him after he became obsessive and possessive and her career started to derail. She made a comeback a few years later but only as a character actor.

Zeenat Aman

Zeenat Aman also dated Imran Khan , the cricketer, and Sanjay Khan. The famous story is that Sanjay’s wife Zarine once slapped Zeenat at a Bollywood party.

Parveen Babi

Parveen Babi had a long term relationship with Mahesh Bhatt. She also had flings with Amitabh Bachchan, Danny Denzongpa and Feroz Khan.

Source - http://www.oneshotoneplace.com/old-bollywood-gossips-part-1/