<figure id="attachment_469859" class="wp-caption alignnone" style="width: 2276px;" aria-describedby="caption-attachment-469859"><a href="#" data-ident_hash="b7859ebb"><img src="https://res.cloudinary.com/fridaydigital/image/private/t_article_image/wpmedia/2026/06/c0f3d3e15e1eaa1767ca5a3cf654772d.jpg" alt=""></a><figcaption id="caption-attachment-469859" class="wp-caption-text">Madonna remains as glamorous as ever, pictured with her current boyfriend, soccer player Akeem Morris, who is 37 years her junior.</figcaption></figure>
<h2> Who was her best lover?</h2>
In Japan&#8217;s entertainment industry, celebrity confessions have been stirring controversy, from Ano&#8217;s (age undisclosed) casting issue to comedian Kota Nakayama&#8217;s (45) alleged bullying scandal involving Savanna&#8217;s Shigeo Takahashi (50). But in America, celebrity revelations are on an entirely different level.
The &#8220;Queen of Pop,&#8221; Madonna (67), has openly revealed the name of the person she considers the best lover of her life.
According to Page Six, while promoting her new album &#8220;Confessions II,&#8221; Madonna took part in a roundtable discussion on the LGBTQ community platform Grindr alongside her friend, playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler, and designer Raul Lopez.
When Lopez asked,
&#8220;Who was the best lover you&#8217;ve ever had?&#8221;
Madonna replied,
&#8220;I can only name someone who&#8217;s already dead.&#8221;
Then, covering her mouth with her hand, she whispered,
&#8220;John F. Kennedy Jr.&#8221;
The revelation left everyone present stunned.
Madonna thus disclosed that she had a brief romance with JFK Jr.—the son of former President John F. Kennedy—during the late 1980s, when she was at the height of her fame.
Lopez then added,
&#8220;Everyone says he was well-endowed and amazing in bed.&#8221;
Madonna nodded with a look of satisfaction and replied,
&#8220;Yes, that&#8217;s right.&#8221;
&#8220;At the time, Madonna was married to actor Sean Penn. Meanwhile, JFK Jr. was dating model Christina Haag when he met Madonna. Nevertheless, it&#8217;s said that the two developed a passionate relationship,&#8221; said a Hollywood insider.
The unexpected pairing of the Queen of Pop and the son of a former U.S. president inevitably brings to mind the rumored relationship between President John F. Kennedy and Marilyn Monroe. Although Madonna and JFK Jr. were reportedly strongly attracted to one another, their relationship did not last because JFK Jr.&#8217;s mother, Jacqueline Kennedy Onassis, opposed it.
&#8220;At the time, Madonna had released the critically acclaimed album &#8216;Like a Prayer.&#8217; The album would later be recognized as one of the greatest albums of all time.
Meanwhile, JFK Jr., the eldest son of the late president, was working as an assistant district attorney in New York while also publishing a magazine, attracting considerable public attention. After delivering a speech at the 1988 Democratic National Convention, he was widely viewed as a future presidential hopeful who might carry on his father&#8217;s legacy. Their relationship was truly a whirlwind romance amid all that attention,&#8221; the same Hollywood insider explained.
JFK Jr. married Carolyn Bessette, who worked for Calvin Klein, in 1996. However, on July 16, 1999, he died at the age of 38 when the small aircraft he was piloting crashed.
Madonna divorced Sean Penn in 1989 after marrying him in 1985. She later remarried British film director Guy Ritchie in 2000, but that marriage also ended in divorce in 2008.
<div data-friday-nextpage-lead="The &quot;difference&quot; between Nakayama and Madonna"></div>
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<figure id="attachment_469862" class="wp-caption alignnone" style="width: 1080px;" aria-describedby="caption-attachment-469862"><a href="#" data-ident_hash="11c1164b"><img src="https://res.cloudinary.com/fridaydigital/image/private/t_article_image/wpmedia/2026/06/3f012e202a24facb009a72a7d9bd78d3.jpg" alt=""></a><figcaption id="caption-attachment-469862" class="wp-caption-text">Ano&#8217;s own confession led to the end of her TV show.</figcaption></figure>
<h2>That&#8217;s just plain bullying</h2>
These days, Madonna is reportedly dating Jamaican soccer player Akeem Morris, who is 37 years younger than she is. The couple continues to show their affection by posting cozy two-shot photos together on their respective Instagram accounts.
Japan has also seen its share of headline-making confessional revelations.
On the May 18 broadcast of TV Asahi&#8217;s &#8220;Ano Channel,&#8221; Ano was asked by a fellow cast member which celebrity she disliked and answered by naming Sarina Suzuki.
Suzuki later expressed her anger on Instagram, writing:
&#8220;That&#8217;s just plain bullying.&#8221;
Following the backlash, both TV Asahi and Ano&#8217;s side issued apologies. Ano herself suggested she would step down from the program, ultimately leading to the show&#8217;s cancellation.
Meanwhile, solo comedian Kota Nakayama stated on an ABEMA program aired on May 5:
&#8220;There&#8217;s a senior comedian who bullied me for about ten years.&#8221;
Although he did not mention a name, online speculation quickly focused on &#8220;Savanna&#8217;s&#8221; Takahashi. As a result, Takahashi found himself compelled to issue an apology.
Nakayama also apologized on his own X account, writing:
&#8220;The expression &#8216;I was bullied&#8217; was completely inappropriate.&#8221;
It was an unusual turn of events, and both Ano&#8217;s and Nakayama&#8217;s confession controversies ended on an unpleasant note.
Revelatory comments made on television often spread rapidly through social media and create unforeseen waves of controversy.
Madonna&#8217;s bold confession, however, may reflect the wisdom gained from decades in show business. By restricting her answer to someone who had already passed away, she avoided commenting on her current partner or any living former lovers, thereby sidestepping unnecessary backlash.
In today&#8217;s social media age, awareness has grown that sexual harassment and power harassment are unacceptable and should be exposed. As a result, celebrity confessions presented as television entertainment can quickly be interpreted online as unforgivable conduct, spreading rapidly under a strong sense of justice and escalating into uncontrollable public outrage.
For that reason, personal revelations of this kind require greater caution and consideration of their potential impact.
Perhaps that is why Madonna&#8217;s daring admission—coming from a woman known for her glamorous romantic history and provocative social media presence—was limited to someone who is no longer alive, demonstrating what can only be described as a remarkably high level of crisis management.

 Ryo Sakamoto (Former head of the Culture and Society Department of Tokyo Sports Newspaper)

 The Image Direct/Afro (Madonna), Takahiro Kagawa (Ano)

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