Celebrity Double Dates Through the Years

Four isn’t always a crowd! When it comes to dating, these celebrity couples are showing Us that sometimes date night is better when paired with another duo.

Whether it’s heading out to dinner or hitting the ski slopes or even attending red carpet events, these celebrities prove that the more is merrier with these iconic double dates.

Kourtney KardashianTravis BarkerMegan Fox and Machine Gun Kelly have been known to turn some heads during their own double dates — like the time the foursome posed touching tongues with their partners in the bathroom at the 2021 VMA Awards.

They aren’t the only stars who love double dates. Scroll down to see some of the most star studded celebrity double dates through the years — and ones that make Us wish we could fifth wheel.

Celebrity Double Dates

Credit: Gotham/GC Images/Getty Images

Blake Lively, Ryan Reynolds, Emily Blunt and John Krasinski

Blake Lively and Ryan Reynolds celebrated pals Emily Blunt and John Krasinski's movie premiere for A Quiet Place in New York City in April 2018. This wasn’t the first time that the dynamic duo was spotted together — they were also seen at New York’s Guggenheim Museum a month prior.

Celebrity Double Dates

Credit: Larry Busacca/Getty Images for NARAS

John Legend, Chrissy Teigen, Behati Prinsloo and Adam Levine

The former Voice costars, John Legend and Adam Levine, spent the night with their two model wives, Chrissy Teigen and Behati Prinsloo. Despite the competitiveness of the two on the show, Legend and Levine are friends off-set with Legend telling Seth Meyers the two had previously “dated in the same circles.”

Celebrity Double Dates

Credit: Vivien Killilea/Getty Images for GQ

Kourtney Kardashian, Travis Barker, Megan Fox and Machine Gun Kelly

Kourtney KardashianTravis BarkerMegan Fox and Machine Gun Kelly dined together after attending the GQ Men of the Year party in November 2022.

Celebrity Double Dates

Credit: Karwai Tang/WireImage/Getty Images

Prince Harry, Meghan, Prince William and Duchess Kate

Prince Harry and his brother Prince William stepped out with their respective wives, Meghan Markle and Princess Kate, for the Royal Foundation Dinner at Victoria House in London in November 2018 before strained relations with the royal family.

Celebrity Double Dates

Credit: Michael Kovac/Getty Images for AFI

George Clooney, Amal Clooney, Cindy Crawford and Rande Gerber

Cindy CrawfordRande GerberGeorge Clooney and Amal Clooney joined forces to attend the American Film Institute’s Life Achievement Award Tribute to George Clooney in June 2018. The foursome have also been seen vacationing together, as the former Casamigos Tequila partners owned side-by-side villas in Cabo San Lucas, Mexico, before selling the properties in 2016.

Celebrity Double Dates

Credit: Courtesy of Keleigh Teller/Instagram

Keleigh Teller, Miles Teller, Julia Garner and Mark Foster

Julia Garner and Mark Foster spent time with the married couple in Portofino, Italy, in September 2023. “I found my love in portofino,” Keleigh Teller wrote via Instagram at the time.

Celebrity Double Dates

Credit: Shareif Ziyadat/FilmMagic

Gabrielle Union, Dwyane Wade, Justin Timberlake and Jessica Biel

Gabrielle UnionDwyane WadeJustin Timberlake and Jessica Biel partied together in New York City to celebrate the NBA star’s retirement in April 2019. The Miami Heat lost to the Brooklyn Nets earlier in the evening during Wade’s final game, but the couples were all smiles celebrating later.

Celebrity Double Dates

Credit: Gotham/GC Images

Naomi Watts, Billy Crudup, Sam Rockwell and Leslie Bibb

Newlyweds Naomi Watts and Billy Crudup sat alongside Sam Rockwell and Leslie Bibb at the 2023 US Open, where they watched Coco Gauff take home the title during the women’s final.

Celebrity Double Dates

Credit: Courtesy of Paul Wesley/Instagram

Nina Dobrev, Shaun White, Keleigh Teller and Miles Teller

Nina Dobrev and Shaun White spent the 4th of July holiday with Keleigh and Miles Teller in 2023. The women put their injuries (Dobrev sporting a cast on her wrist, with Keleigh wearing a boot on her foot) on full display with Dobrev playfully urging everyone to “Be safe, it’s dangerous out there,” via Instagram.

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