Has Madonna Taken Dating Inspiration from Leo DiCaprio? We Analyzed the Data.

It seems that Madonna has taken dating inspiration from Leo. But has she?

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There’s a long running joke that Leo DiCaprio refuses to date a woman over the age of 25. A chart posted to Reddit went viral when it showed DiCaprio’s clear history of dumping women once they got to that ripe age of 25.

And there’s been a lot of speculation as to if Madonna herself is capable of dating anyone close to her age. Apart from her marriage to Sean Penn in the 80s (he’s only 2 years younger) and a brief series of dates with Michael Jackson (he’s 5 months younger), it does seem that the music icon and sex symbol is set on going for younger men.

In fact, it seems that as Madonna gets older, her partners get younger, with her last couple boyfriends being at about the same age as her oldest children. Lourdes Leon is not quite 26 and Rocco Ritchie just turned 22.

Intending to get to the bottom of this, we did the math and looked at the data. We put it in a nice chart for you (albeit, it’s not as fancy as Reddit user u/TrustLittleBrother’s graph, but whatever). And low and behold, the data is quite interesting.

Here is the list of pretty much everyone (apologies to anyone missing) whom Madonna has been rumored to date (or marry) since 1991. In the graph that follows, you can see the age differences in the gray-colored bars. The last year of the relationship was listed on the graph to keep things simple.

List of Madonna’s Alleged Intimate Partners Since 1991

2022: Andrew Darnell, 23;  Madonna, 64                           

2019 – 2022: Ahlamalik Williams, 25-28; Madonna, 61-63

2017: Kevin Sampaio, 31; Madonna: 59

2016: Aboubakar Soumahoro, 36; Madonna, 58

2014: Timor Steffens, 26; Madonna 57

2010-2013: Brahim Zaibat, 20-23; Madonna, 52-55

2008-2010: Jesus Luz, 21-23; Madonna, 50-52

2008: Alex Rodriguez, 33; Madonna, 50

2000-2008: Guy Ritchie, 32-40; Madonna, 42-50 (Married)

1998: Chris Paciello, 27; Madonna, 40

1997-1998: Andy Bird, 32-33; Madonna, 39-40

1994-1997: Carlos Leon, 28-31; Madonna, 36-39

1994: Jenny Shimizu, 27; Madonna, 36

1994: Dennis Rodman, 33; Madonna, 36

1994: Ingrid Casares, 20; Madonna, 36

1994: Tupac Shakur, 23; Madonna, 36

1991-1992 Vanilla Ice, 23-24; Madonna, 33-34

Graph of Madonna’s Romantic Age Gaps

Chart of Madonna's romantic age gaps

Graph of Leonardo DiCaprio’s Age Gaps (from u/TrustLittleBrother via Reddit)

A Summary of the Data

Madonna’s age preference averages slightly higher than Leo’s at 28.23 at the outset of her relationships. That number is a little lower when analyzing the start of her relationships, sitting at 27.06. When looking at the statistical mode, however, the most common age of one of Madonna’s lovers at both the start and end of her relationships is 23.

We also found that the average age difference over the years has been 16 years, with Madonna always the senior. However, as you can see, the closer you get to 2022, the higher the gray bar becomes. The final intimate partners’ age differences hovered around 30-40 years.

So, has Madonna been taking inspo from Leo? It’s hard to say. First of all, Leo was born in 1974 (sorry, probably too old for Madge) and his graph starts at 1999. That’s not to say that he wasn’t dating before that. We just don’t have the data.

However, there is a clear trend of increasing age gaps beginning around 2010. The age gap is comparable to Leo’s, which started rapidly increasing around the same year.

Our conclusion? It’s possible that Madonna’s dating preferences have been inspired by Leo, but we would need to ask her.

What do you think?

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