May December Romances Among Hindi Film Celebrities!

This is an off-shoot of the discussion we’ve been having off and on about Ranbir-Alia and our conflicting emotions as celebrity watchers. They are hardly the first May-December romance in Hindi film, many of them even more famous and with an even greater age difference. So I thought it might be moderately worthwhile to quickly run through some other similar romances.

Amrita Singh-Saif Ali Khan

Image result for amrita singh saif ali khan

Gonna start with the slightly odd one out! Amrita was born in 1958. She is from an old Delhi family with some minor film connections thanks to an aunt who was an actress and married to Dilip Kumar’s younger brother. Amrita started acting at 25 and immediately became a hit. At 33, Amrita met 21 year old princeling Saif Ali Khan at a party, he was immediately smitten and chased after her. He convinced her to go on a date, and at the end of the night he went back to her house with her and never left. They were married shortly after. Amrita more or less stopped acting, and Saif became the primary worker and wage earner for their family while Amrita stayed home with their two children. They had a stormy marriage and divorced when Amrita was 46 and Saif was 34. Saif went on to have a public relationship with a woman named “Rosa”, and then to date and live with Kareena Kapoor for years before marrying her.

Dharmendra-Hema Malini

Image result for dharmendra hema malini

Dharmendra was born in 1935 and married before he was 20 in a semi-arranged marriage. He came to Bombay to become an actor, leaving his wife and children back in his home village. He started an affair with Meena Kumari, the biggest actress in the industry who was 2 years older than him. The affair burned out after a year and Dharmendra brought his wife and children to Bombay to be with him. In 1970, he was cast opposite a young actress from the south, Hema Malini, for the first time. Dharmendra was 35 and Hema Malini was 22. She had been acting professionally since she was 14 (and possibly fudged her age a few years down at some point). Malini was courted by multiple leading men of the industry at once, but by 1974 while filming Sholay, Dharmendra took the lead. Their relationship continued for 6 years until they finally married (with Dharmendra never officially leaving his first wife) in 1980, when Dharmendra was 45 and Hema was 32.

Dilip Kumar-Saira Banu

Image result for dilip kumar saira banu

Dilip was born in 1922. He came to Bombay with his family as a teenager and fell into acting at 22 because he was offered a job. He got his first hit film at 25, and became a major star in 1949 when he was 27. He had a serious relationship with one of his first co-stars, but she was married. He rebounded with his most famous love affair, Madhubala. After that relationship died, Dilip had a series of light affairs with multiple women, none of them making it to the point of being official and public, and Dilip himself acknowledges the relationships but does not give names as it would not be gentlemanly. Meanwhile, Saira Banu was born in 1944. Her grandmother was a film personality, Dilip Kumar was a family friend. Saira loved to hear stories about him, and had a massive crush on him. She used to pray every night that someday she would marry him, and when she went to finishing school in London, she asked to take Urdu lessons partly because Dilip spoke Urdu. At 16, in 1960, she was launched in films. She was suggested as a heroine for Dilip soon after, but he refused because he felt she was too young for him. Saira was angry with him for a few years and avoided him on studio sets. Finally, Dilip was invited to her 21st birthday party and saw her in a new light that night. A few days later he called her up and invited her for a drive, and proposed immediately. When they married in 1966, Dilip was 43 and Saira was 21.

Aamir Khan-Kiran Rao

Image result for aamir khan kiran rao

Aamir Khan was born in 1965. He fell in love with the girl next door as a teenager and married her (in the face of moderate opposition) 3 days after he turned 21. His film career started in a small part in an art film when he was 19. His first big launch movie was when he was 23, Qayamat Se Qayamat Tak, and he immediately became a major star. He did a variety of mainstream films for the next 10 years before starting to move towards a more artistic kind of career. In 2000, while filming Lagaan, Aamir is wildly said to have started an affair with a British journalist covering the filming, Jessica Hines, which resulted in a child. Neither parent has ever confirmed this. 2000 is also when Aamir first met Kiran Rao. Kiran was 27 and Aamir was 35. Kiran had a masters in communication and this job on Lagaan was the start of her hoped for career as a director. Aamir divorced his first wife in 2002 when he was 37. At some point, he called up a mutual friend and asked if Kiran Rao was still in a relationship as she had been during the shoot of Lagaan. He learned she was single, called her up, and they started dating. They married in 2005 when Aamir was 40 and Kiran was 32.

Saif Ali Khan-Kareena Kapoor

Image result for saif ali khan kareena kapoor

Saif was born in 1970, raised in a very cosmopolitan way all over India and the world by his extremely famous parents. He finished at an exclusive British boarding school, then came back to India and started bumming around a bit, worked in advertising for two months, got a job in a TV commercial, was offered a film role, and decided to come to Bombay and try to make it in movies. He met Amrita Singh before he had finished his first movie and married her. His first 3 years as an actor he went mostly unnoticed, finally in the mid-90s began to be appreciated as a boyish second lead type. In 2001, at age 31, Saif finally got appreciated for his scene stealing performance in Dil Chahta Hai. 2 years later, he was cast opposite Kareena Kapoor for the first time. Kareena was the younger sister of Karisma Kapoor, who had co-starred with Saif once in Hum Saath Saath Hain in 1999 when Kareena would have been 19. Saif also worked with Karisma in a brief cameo in Yeh Dillagi in 1994 when Kareena would have been 14. It is certainly likely that Saif briefly met Kareena at some point before she was 19 (although also possible they didn’t meet since Kareena was at boarding school in her teen years), and he most likely did meet her in 1999. Kareena was launched in film in 2000 at age 20. By 2003 when she and Saif co-starred for the first time, Kareena was deep into a public relationship with Shahid Kapoor, and Saif’s marriage to Amrita was falling apart as he started a relationship with his girlfriend Rosa. 5 years later, they co-starred again, Kareena was 28 and recently broken up with Shahid. Saif had broken up with Rosa and was 38. They started a serious public relationship almost immediately, were together for 4 years including living together for the last few, and then married when Kareena was 32 and Saif was 42.

Thoughts? Stories you want to know more about? Gut reaction of “oh I love them as a couple” or “oh I hate them as a couple”?

24 thoughts on “May December Romances Among Hindi Film Celebrities!

  1. I didn’t know Saif’s first wife was older than him! Yeah, he and Kareena are fine. He’s not a creepy controlling predator and she had that very open relationship with Shahid and dated Saif for years before making it legal.

    The rest of those stories, woo, Bollywood is wild. Dharmendra taking a second wife when it’s not religiously sanctioned (isn’t that bigamy?). Dilip and Saira, it’s uncomfortably close to the plot of Lamhe except for resembling the dead mother. Amir isn’t creepy for marrying Kiran but not acknowledging his kid publicly is booo Aamir booo, I’m so sad you’re like Steve Jobs.


    • There’s a whole Thing about Dharmendra and Hema. They are different religions, he is Sikh and she is south Indian Hindu. But polygamy isn’t necessarily horrible from both traditions. However, if you are legally registered as Hindu or Sikh, it is illegal for you to marry twice. At the time it was widely understood that Dharmendra converted to Muslim on paper in order to have a second wife, but now he denies doing that, so I have no idea what happened. Maybe it was a religious but not legal ceremony?

      Saira and Dilip are so cute together now, this sweet old couple, but wow their early romance was odd. And later on, Dilip took a second wife and then promptly divorced her. It sounds like a confused situation he felt trapped into, but it was quite the scandal at the time.

      Amrita and Saif were a big big story when it happened. It really was remarkable, she was “old” and he was barely 21, and a little princeling who had been raised in the public eye, and completely obsessed with her. It would be like if Aryan Khan suddenly moved in with Katrina Kaif and announced he was in love with her forever and ever and they were married less than 2 months later and she retired to raise their kids while Aryan went out to try to find a job.

      Agree about Kareena and Saif. There’s a 10 year age difference there, it was kind of a Thing when they first got together because he was divorced and all that, but after 4 years together the public got used to it and they certainly seemed to have worked stuff out.

      With Aamir, I am reserving judgement. We don’t know what’s happening in reality, maybe Jessica refuses to give him any contact and he has decided the best thing he can do is nothing. Maybe he sends gobs and gobs of child support but isn’t allowed access. Maybe Jessica asked him not to officially acknowledge the child in order to let him have a normal childhood, maybe Aamir made that decision. Or maybe it’s just a rumor and not true. I mostly repeat it because it would be easy to think that Kiran broke up his marriage, and I don’t think that is true, because if they were having an affair on the sets of Lagaan then why are there all these Jessica Hines rumors for the same period? I find it easier to believe the official version, Kiran was with someone back then, Aamir’s life was a mess, and a couple years later he tracked down and called up that cute little AD he remembered from Lagaan.

      On Sat, Dec 7, 2019 at 4:43 PM dontcallitbollywood wrote:



      • Jessica has given public interviews saying Aamir does not want to be associated with her or be a father to Jaan. She said she told her son the same thing.

        Last year, he accidentally followed Jessica on instagram. It was noticeable because he doesn’t follow anyone else. One or two days later, he unfollowed her again. His PR must have been good because outside of BW forums, it did not make it into the news. My guess is that he was trying to look at pictures of Jaan and accidentally pressed the follow button.

        The Dilip Kumar – Sairu Banu thing totally creeps me out. The age difference is bad enough but it’s not like he was loyal to her either. He had a major affair and left her for another woman. He married the second woman and then left her also two years later and returned to Saira Banu. It’s revolting.

        Liked by 1 person

        • Jessica just feels slightly loopy to me. I can believe she is lying about Aamir in any variety of ways. the mere fact that she is giving these public interviews makes me distrust her instincts as a mother.

          I ready Dilip’s whole autobiography looking for an explanation of the second marriage, and he ducks the whole thing. In very obscure and circular language, he seems to imply that the woman entrapped him under false pretenses, with the assistance of his sister and brother-in-law who introduced them. Basically that she played the role of an innocent woman in love with him, seduced him, forced him to marry her, and as soon as he learned it was all a lie, he left her. That’s Dilip’s Best Possible version of things, and it’s still creepy! Right? Even if she was older and divorced and so on instead of how she presented herself, she was still a woman much younger than him that he let himself fall in lust with despite being married.


          • I don’t know the details but regardless of whatever that woman presented herself as, he still had an affair and married her even though he already had a wife. He can spin that any way he wants but it doesn’t become any better. So if she had been good enough, his behavior would have been excusable and justified according to him. Trash.

            Liked by 1 person

          • Yep, totally agree. And Dilip in his book doesn’t even say “that was a wrong thing I did” exactly. He gives excuses, and says he is sorry he hurt Saira and she is a saint for forgiving him. But he doesn’t say “I was wrong and bad and no good”.


      • It would be like if Aryan Khan suddenly moved in with Katrina Kaif and announced he was in love with her forever and ever and they were married less than 2 months later and she retired to raise their kids while Aryan went out to try to find a job.

        ****praying to the gossip gods that this actually happens****

        Jaan looks EXACTLY like Aamir. Of course we don’t know what’s going on behind the scenes, maybe he has contact, maybe he doesn’t, I hope to God he at least sends a damned check. I remember the photo with Jessica, Jaan and Anupam, that seemed…pointed.


        • I recall Jessica saying somewhere that Aamir has no contact with Jaan and doesn’t acknowledge him but that she doesn’t care anymore because she’s married now and her husband is a great dad to Jaan.

          Those interviews are very old though. She hasn’t talked about Aamir in a really long time.


          • And again, the fact she is giving the interviews makes me nervous about believing her. How is that an okay thing to say in public about your son who can’t make the decision for himself?


          • As I said, those are very old interviews. She hasn’t talked about Aamir in a really long time. Her bitterness is understandable so her giving interviews when Jaan was very small doesn’t sound crazy to me.

            It’s really not unheard of for men to behave this way. Jessica was just a useless fling for Aamir so he wants nothing to do with her or any child from it because it’s a part of his life he probably wants to forget. You see it all the time where the person is a good parent to his other kids but won’t take on something like this. Even if he’s a good parent to one child doesn’t mean he would be a good parent to all of them.

            Look at Boney Kapoor. He wanted the Mona part of his life to be over so he abandoned the kids too. He was mostly an absentee father for Arjun and Anshula but a great dad to Sridevi’s kids. It would of course cause resentment for the ones left behind.

            Liked by 1 person

          • Speaking of which, isn’t it interesting that Boney and Sridevi feel like a May December romance but actually Mona was a year younger than Sridevi? All of the ones I describe here were love matches with real romances, but there’s also all those arranged couples where a decade age differences was considered just a healthy good idea.


        • The fact that Aamir is a super involved father with his other 3 children, including the two born to a woman who he is no longer married to, makes me think he can’t be a total deadbeat.

          And yes! When I was writing out the Aryan example, I found myself going “oh my gosh, could this actually happen?”

          On Sat, Dec 7, 2019 at 6:15 PM dontcallitbollywood wrote:



          • But Aamir isn’t super-involved with his two older kids either. Yes, they see him on holidays and stuff like that but Aamir himself says that he is too involved in himself and his own things to be that kind of dad. I’ll see if I can find the interview.

            Liked by 1 person

  2. I don’t really see the Alia/Ranbir thing as May December. I see it more as May/Martian. (Apologies to any Martians reading this.)


    • It is, indeed, very strange! And I wonder if these others only seem “normal” to us because we are coming at them years later, knowing the couple as a couple. But I don’t think so. I mostly remember when Kareena and Saif got together, and it was strange and people talked about it a lot, but it wasn’t this total shock of “NO! Really? NO!”

      On Sat, Dec 7, 2019 at 8:47 PM dontcallitbollywood wrote:



  3. Hm. I wouldn’t consider most of these May December. Maybe Dilip and Saira, but more because she was so young than because he was so old. Can’t get upset about all the women who had consensual relationships with men 8-12 years older, and then married in their early thirties. That describes me and many others I could name. Sometimes the age difference isn’t reflected in self-awareness or knowing what you want out of life. Aamir and Kiran seem that way to me, for instance, very evenly matched, same with Saif and Kareena. What I find icky is when there’s a power difference, which is more likely when the woman is very young, or if she enters into the marriage not entirely by her own choice.


    • What about 21 year old Saif and 33 year old Amrita? Personally I give that one a pass because Saif had such a strange adventurous life (boarding schools all over the world, very kind of rich brat party life), and Amrita was apparently not interested in marriage until he convinced her. So it doesn’t feel like the older partner picking a naive younger partner and rushing them into marriage, more two random different people who surprisingly fell in love. But, on the other hand, it is a barely 21 year old marrying a 33 year old after knowing her for only weeks. On paper that does not look like a healthy power dynamic.

      I agree about the age difference versus where you are in life. For me, with Saif and Aamir, the second marriage kind of feels like a reset button. They married very very very young, grew apart from their spouse, where trying to figure out who they were and what they wanted and start fresh at the same time they met someone 10 years younger than them who was also trying to figure out who they were and what they wanted in life. And then the new couple sort of grew into the world together. In that way, I like it better than if they hadn’t married, and you had someone fully settled in what they want from life and who they are, getting together with someone who is still finding themselves.

      On Sat, Dec 7, 2019 at 9:46 PM dontcallitbollywood wrote:



      • Saif and Amrita, the power dynamic in terms of gender and status and money makes it hard to see Saif as an innocent taken advantage of in that situation. More like entitled young man. So that’s an exception to the age rule. She was also just not that much older. I really do think 20+ years is a different ballgame.

        I want to believe Saif and Aamir are getting a second chance with a partner who is the right match for this stage of life. It’s hard to say how it felt to the people inside those relationships, though, especially the first spouse and children. Sometimes people are happier apart, sometimes only one person wants out, sometimes infidelity breaks up a marriage. Don’t know why o feel more judgey about, say Adi and Rani than Saif and Kareena. I know equally little about them from the outside.


        • Saif was definitely a privileged young man, hardly feels like Amrita took advantage of him, more like he was the one driving for it. And based on the Koffee he and Sara did recently, the marriage was in real bad shape by the end of it and he and Amrita are better as parents and people now that they are apart. So I feel pretty good about that. Saif and Kareena can be happy with my blessing.

          I have to admit I have little sympathy for Adi’s first wife for almost no reason. I knew she held him up for a big big settlement in the divorce. Not that there is anything wrong with that, but it makes me feel better about her, like maybe she wasn’t totally broken by the end of her marriage.

          On Sun, Dec 8, 2019 at 11:55 AM dontcallitbollywood wrote:



          • I think the fact that Aamir’s first wife runs his foundation and appears in public with him and Kiran says a lot. I watched the documentary on the making of Lagaan and she was such a badass. I think she’s a strong person and if she wasn’t comfortable continuing to associate with Aamir she wouldn’t do it.


          • Agree. And in Aamir’s Koffee interview, he made a point that Kiran and Reema have a relationship separate from him, and that was Reema’s choice.

            On Sun, Dec 8, 2019 at 1:43 PM dontcallitbollywood wrote:



  4. I agree that Dilip-Saira are adorable now but their relationship trajectory is still way too weird for me. I think it is generally regarded as cute now, only because they are so much older and still together.

    Another May-December relationship I found super gross was Rajesh Khanna and Dimple’s relationship. She was 16 and he was 31 when they got marries!!! She was just a frickin teenager! Also, while the “official” reports says they were married around March 1973 (6 months before release of Bobby) and Twinkle was born Dec 24, 1974, Rishi made that creepy comment that Dimple was pregnant with Twinkle during the filming of Bobby. So that timeline makes no sense to me. Maybe they will still filming Bobby 6 months before release. Anyways, it was all too icky for me. Glad Dimple found happiness with Sunny.


    • YES!!!! My current interpretation of Dimple-Rajesh is that he probably seduced her and got her pregnant (sounds like he went after a lot of women), and then got pressured into marrying her. And she was BARELY 16 at the wedding, he really married a 15 year old. And possibly impregnated a 15 year old. Good on him, I guess, for marrying her. But bad on him for everything else. And that relationship was clearly never going to work. I can see why Dimple told Twinkle to live with Akshay for at least a year before even getting engaged.

      On Mon, Dec 9, 2019 at 11:43 AM dontcallitbollywood wrote:



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