Taylor Swift and Travis Kelce aren’t the only celebs to have a romantic engagement

Grand romantic gestures don’t always lead to everlasting love. Take note, Taylor Swift and Travis Kelce.

The Minnesota Star Tribune
September 3, 2025 at 4:56PM
Kansas City Chiefs tight end Travis Kelce kisses Taylor Swift after the 2024 Super Bowl. (John Locher/The Associated Press)

Taylor Swift and Travis Kelce caused millions of fans to swoon when they used Instagram last month to plug their engagement, sharing various photos from a Kansas City courtyard with the caption: “Your English teacher and your gym teacher are getting married.”

Cute. But when it comes to originality, the lovebirds’ social-media splash paled in comparison to other celebrity proposals. Here are nine others that were really spectacular, often outshining the actual relationships.

Prince Rainier III and Grace Kelly celebrate their 1956 wedding. (RPA United Press)

Grace Kelly and Prince Rainier III

Date: Jan. 5, 1956

Popping the question: If you measure love by the carat, it’s hard to top this proposal. The Prince of Monaco presented his bride-to-be with two stunning rings, including one dazzler that practically blinded Kelly’s co-stars in her final film, “High Society.”

Love conquers all? Kelly chose royal duties over building on her Oscar-winning career, retiring from the screen at the age of 26.

Marriage: April 18 and 19, 1956, (a two-day wedding!) until Kelly’s death in a 1982 car accident.

Johnny Cash and June Carter Cash perform at New York's Radio City Music Hall in 1985. (RON FREHM/The Associated Press)

June Carter and Johnny Cash

Date: Feb. 22, 1968

Popping the question: The daughter of country-music royalty had already turned down the brash Man in Black several times, before a joint concert in London, Ontario. After the duo performed “Jackson,” Cash asked for her hand in front of 7,000 fans. This time she said yes.

Love conquers all? Cash was still deep in the throes of a serious drug and alcohol addiction. He eventually found sobriety.

Marriage: Lasted until Carter’s death in May 2003; Cash passed away four months later.

Ahmad and Phylicia Rashad co-hosted "Friday Night Videos" shortly after their marriage. (NBC)

Phylicia Ayers-Allen and Ahmad Rashad

Date: Nov. 28, 1985

Popping the question: The former Minnesota Viking was sweating like he was in the Super Bowl when he broke away from a Detroit Lions field report to ask studio host Bob Costas to track down his “Cosby Show” girlfriend from the Macy’s Thanksgiving Day Parade. Costas agreed to pass along the proposal, but only if he could get tickets to the sitcom’s taping.

Love conquers all? Bill Cosby walked his TV wife down the aisle; Rashad’s best man was OJ Simpson.

Marriage: Dec. 14, 1985-early 2001.

Barack Obama and Michelle Obama at the 2024 Democratic National Convention. (Melina Mara/The Washington Post)

Barack Obama and Michelle Robinson

Date: July 31, 1991

Popping the question: At a dinner celebrating the fact that he had just passed his bar exam, the future president pretended that he didn’t see the point of marriage. Before his date could reach across the table and grab his throat, a waiter presented a dessert plate holding an engagement ring. “It had all been a ruse,” Michelle Obama wrote in her book, “Becoming.” “It took me a second to dismantle my anger and slide into joyful shock.”

Love conquers all? Michelle, who was Barack’s boss when they met, thought his initial advances were “completely tacky.”

Marriage: Oct. 3, 1992-present.

Seal and Heidi Klum take in a LA Lakers game in 2009. (Mark J. Terrill/The Associated Press)

Heidi Klum and Seal

Date: Dec. 23, 2004

Popping the question: The Grammy winner wooed the supermodel during a Christmas skiing trip in Whistler, British Columbia, whisking her by helicopter to the top of a glacier where a specially designed igloo was waiting.

Love conquers all? A month before the proposal, Seal released a greatest-hits collection that include a new cover of “Walk On By,” a tearjerker about a bitter breakup.

Marriage: May 10, 2005-Oct. 14, 2014.

Tom Cruise and Katie Holmes enjoy a kiss in Rome in 2005. (CORRADO GIAMBALVO/The Associated Press)

Tom Cruise and Katie Holmes

Date: June 17, 2005.

Popping the question: Less than a month after nearly destroying Oprah Winfrey’s couch, the “Top Gun” star ushered the “Dawson’s Creek” vet to the top of the Eiffel Tower where he asked for her hand instead of bungee jumping.

Love conquers all? The early-morning proposal was followed by a press conference for “War of the Worlds” in which a beaming Holmes didn’t say a word.

Marriage: Nov. 18, 2006-June 29, 2012.

Kim Kardashian and Kanye West at a 2020 Vanity Fair Oscar party. (JEAN-BAPTISTE LACROIX/AFP/AFP)

Kim Kardashian and Kanye West

Date: Oct. 21, 2013 (Kardashian’s 33rd birthday)

Popping the question: The rapper rented out San Francisco’s AT&T Park for the event, recruiting a 50-piece orchestra that played Lana Del Rey’s “Young & Beautiful” in the background. Loved ones hid in the dugout, emerging to a spectacular fireworks display.

Love conquers all? The Giants, who had won the 2012 World Series, finished third in their division in 2013, missing the playoffs.

Marriage: May 24, 2014-March 2, 2022.

Charly Defrancesco, left, and Marc Jacobs (Evan Agostini/The Associated Press)

Marc Jacobs and Charly Defrancesco

Date: April 4, 2018

Popping the question: A Chipotle restaurant may not be the most romantic — or most sanitary — place to get down on one knee, but fashion designer Jacobs made up for the low-brow setting by hiring a flash mob to celebrate the event with a performance to Prince’s “Kiss.”

Love conquers all? Did we mention Chipotle?

Marriage: April 6, 2019 to present.

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Nina Dobrev and Shaun White

Date: Oct. 30, 2024

Popping the question: “The Vampire Diaries” star thought she was attending a fashion show. But she got suckered. It was all a ruse by the Olympic-winning snowboarder, who capped his successful misdirect with an order from Shake Shack.

Love conquers all? The couple, who have been together since 2019, have still not tied the knot.

Marriage: Stay tuned.

about the writer

about the writer

Neal Justin

Critic / Reporter

Neal Justin is the pop-culture critic, covering how Minnesotans spend their entertainment time. He also reviews stand-up comedy. Justin previously served as TV and music critic for the paper. He is the co-founder of JCamp, a non-profit program for high-school journalists, and works on many fronts to further diversity in newsrooms.

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