While promoting her remix album Finally Enough Love: 50 Number Ones last summer, Madonna famously said that getting married was “maybe not the best idea.”

The 65-year-old singer has been wed twice. The first time was to actor Sean Penn, from 1985 to 1989, and the second time was to filmmaker Guy Ritchie, from 2000 to 2008.

Both marriages ended in divorce and Madonna hasn’t been in a serious public relationship since. (Though she’s cycled through her fair share of 20-something boy toys.)

Lucy Winkett is a professional soprano and the rector at St. James’s Piccadilly in London. In December 2000, she received a call from someone asking if she would be available to perform at an anonymous celebrity’s wedding.

She turned down the offer.

“The man I was speaking to wouldn’t tell me who was getting married, just that it was very high profile,” Winkett recalls in a new interview with The Guardian. “I was intrigued, but it was the run-up to Christmas and I knew I’d be busy, so I said no.”

The man wouldn’t give away the celebrity’s name, but Winkett held firm in wanting more details.

“I insisted on knowing who it was before I committed.”

When he finally gave in and told her it was the reigning Queen of Pop, Winkett says she was “gobsmacked.”

“I’m not very into pop culture, so I hadn’t expected to have heard of the celebrity. But everybody knows Madonna. As a teenager in the 1980s, I used to dance to her music. I never imagined that one day I’d be at her wedding.”

So, of course, she said yes.

A meeting between Winkett, Madonna, and the pianist was arranged, during which the pop goddess said she wanted the aria “Caro Mio Ben” by the Italian composer Giordani performed from a balcony.

The wedding was scheduled for December 22, 2000 at Skibo Castle in Scotland. The day before, Winkett says she arrived at the venue for a rehearsal and was confronted by absolute chaos.

“As we drove through the gates of the castle the next day for rehearsals, there were security people with sticks prodding the hedges and bushes looking for journalists,” she recalls. “That was surreal. Florists, caterers, DJs and others worked ceaselessly to get everything ready.”

Not that any of this was surprising. The most famous woman in the world at that time was about to get married. Of course there might be paparazzi lurking in the bushes!

On the day of the wedding, Winkett says she was excited but nervous.

“I sang from a balcony overlooking the guests, trying not to think about the incredible singers and musicians in front of me,” she recalls. “Afterwards, I spoke to Sting. He said I’d done so well and laughed that it was a tough crowd. I was starstruck.”

“Drinks and dancing followed, with dinner. Madonna came over to say a big thank you. She said it was exactly what she had been hoping for.”

Winkett says she has never spoken publicly about the gig of her lifetime. Even after tabloids got wind of the alleged guest list and started reporting on it, she says nobody except the 60 people in the room ever knew she had been there.

Until now, that is.

“I was pleased. I enjoyed it being a secret. Later, I saw a report that the singer was Luciano Pavarotti,” she recalls.

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Madonna filed for divorce from Ritchie in October 2008, citing irreconcilable differences. At the time, she was in the middle of her record-breaking Sticky & Sweet Tour, during which she dedicated the song “Miles Away,” about a relationship growing apart, to the “emotionally retarded.” 😬

“This song is for the emotionally retarded,” she said during a performance in Boston. “You might know a few people who fall into that category. God knows I do.”

Speaking to Esquire in 2009, Ritchie said of his ex-wife, “She’s a manifester, if there ever was one. First-rate manifester. Madonna makes things happen. Put Madonna up against any 23-year-old, she’ll outwork them, outdance them, outperform them. The woman is broad.”

Then came the cringy kicker: “And, of course, here you go: I still love her. But she’s retarded, too.”

(We’d like to think neither of them would use that word today!)

Reflecting on the couple’s failed eight-year marriage, which resulted in Madonna forking over a reported $75 million to Ritchie in the divorce settlement, Winkett tells The Guardian, “I was sad when I heard that Madonna and Guy got divorced in 2008. Not all marriages last forever, though I’d certainly say yes if Madonna wanted me to sing at her wedding again.”

Considering Madonna’s past remarks on marriage, we’re not sure another wedding is ever gonna happen. Then again, she has reportedly been getting close with 34-year-old British boxer Richard Riakporhe.

Could the third time be the charm? 😉

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