Sandra Bernhard confessed that ‘it really makes me sad’ that she and Madonna were unable to ‘maintain’ their friendship.

The pop star and the comedian became famously close gal pals in the 1980s when they were both acting onstage in New York City.

In a TV moment that became an instant classic, Madonna and Sandra wore matching outfits and flirted with each other on Late Night With David Letterman in 1988.

However, by 1992, their close bond had mysteriously evaporated – and rumors have been flying ever since as to the reason.

Now Sandra has reflected wistfully about her ‘perfect time’ with Madonna, on an episode of Modern Family star Jesse Tyler Ferguson’s podcast Dinner’s On Me.

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Sandra Bernhard confessed that ‘it really makes me sad’ that she and Madonna were unable to ‘maintain’ their friendship; pictured in 1988 on Late Night With David Letterman

They first struck up their friendship in 1988 when Madonna was starring in David Mamet’s play Speed The Plow on Broadway.

Meanwhile Sandra was performing her off-Broadway one-woman show Without You I’m Nothing, which she turned into a movie shortly thereafter.

Now, more than three decades after their friendship fell apart, Sandra remarked that she ‘would be fine’ running into Madonna again now.

‘But I mean, I don’t know what it would be, you know? I mean, and I hate getting nostalgic and caught up in, you know, that time, because it was such like the perfect time,’ she said, looking back on her life and career in the late 1980s, with frequent Letterman appearances and her successful stage show.

‘So there are times when I’m like – it really makes me sad that we couldn’t maintain our friendship,’ she said, adding cryptically: ‘I mean, I could have.’

Sandra’s close friend, fashion designer Isaac Mizrahi, previously shared his sensational theory that a love triangle had caused her to fall out with Madonna.

Isaac alleged that Sandra had been dating the buzzy nightclub owner Ingrid Casares, with whom Madonna then conducted an ‘affair.’

‘I wasn’t sure what Madonna was up to with Sandra,’ he said on the Hot Takes & Deep Dives podcast. ‘I know that Madonna is pansexual…and I guess I couldn’t tell what was going on between them. I couldn’t tell if they were having an affair or whether Madonna was after Sandra’s girlfriend, who was beautiful, this girl called Ingrid.’

Now Sandra has reflected wistfully about her ‘perfect time’ with Madonna, on an episode of Modern Family star Jesse Tyler Ferguson’s podcast Dinner’s On Me; pictured 2021

The pop star and the comedian became famously close gal pals in the 1980s when they were both acting onstage in New York City; pictured at the Brooklyn Academy Of Music in 1989

In a TV moment that became an instant classic, Madonna and Sandra wore matching outfits and flirted with each other on Late Night With David Letterman in 1988

However, by 1992, their close bond had mysteriously evaporated – and rumors have been flying ever since as to the reason; pictured 1991

Ingrid became a sizzling media figure in the 1990s, wafting about amid a flurry of celebrity friends including Donald Trump and Tommy Mottola.

She once claimed that Sandra and Madonna feuded because Sandra was not asked to be one of the models in Madonna’s Sex book.

Isaac, however, disputed Ingrid’s version of events, saying: ‘The truth is Sandra was betrayed because Madonna had an affair with Ingrid.’

He insisted Sandra ‘couldn’t care less’ about the Sex book and never expressed any desire to be one of the models included in the project.

‘None of us really thought much of that book,’ said Isaac pointedly. ‘That book was, you know, a little bit forced, a little bit contrived.’

Now, more than three decades after their friendship fell apart, Sandra remarked that she ‘would be fine’ running into Madonna again now; pictured 1991

Sandra’s close friend, fashion designer Isaac Mizrahi, has sensationally claimed she and Madonna had an alleged love rivalry over Ingrid Casares; Ingrid and Sandra pictured in 1991

When Sandra herself went on the same podcast a year earlier, she was vaguer about the end of her friendship with Madonna – although she hinted that the media scrutiny involved had become a strain on her.

‘I didn’t really like that level of visibility and having to work it constantly,’ said the Roseanne actress. ‘We all as performers work it to a certain degree, but I’m a very improvisational person, on stage and in my life, and I don’t like being tied down in having to be a certain way for my image.’

Sandra added: ‘What I tried to impart in our friendship is: “I’m really your friend, I’m not just somebody that’s passing through.”

She reflected: ‘And I guess for a while we had a real friendship, but it’s hard for somebody like her. She doesn’t really want somebody around who reflects too much of who she is. Therefore, her relationships just don’t last.’