Jackie Sandler and Adam Sandler attend SNL50: The Anniversary Special on February 16, 2025 in New York City ; Ben Stiller and Christine Taylor attend the 2025 Vanity Fair Oscar Party on March 02, 2025 in Beverly Hills, California. Credit :
Taylor Hill/FilmMagic ; Neilson Barnard/Getty
Happy Gilmore 2 came out on Netflix on July 25, and many of the original cast have reprised their roles.
The titular character’s love interest, Julie Bowen’s Virginia Venit, is back and has a family with Gilmore, while Christopher McDonald, Dennis Dugan and Kevin Nealon are also returnig. There are new faces too, including Benny Safdie, Bad Bunny and Margaret Qualley.
While Sandler’s Happy Gilmore may be happily in love with Virginia, the actor has had a real-life love story of his own for over 20 years with his wife, Jackie Sandler. Likewise, McDonald, who plays Gilmore’s foe, has been married for over 30 years.
Here are the real-life loves of the Happy Gilmore 2 cast.
Jackie Sandler and Adam Sandler at the 2024 People’s Choice Awards on February 18, 2024 in Santa Monica, California. Todd Williamson/NBC via Getty
Sandler plays Happy, who finds himself living a happily married life with his love interest from the original film, Virginia.
In real life, however, Sandler met his wife, Jackie, on the set of the 1999 movie Big Daddy, and they have been married since 2003. They have two daughters together: Sadie, who was born in May 2006, and Sunny, who was born in November 2008.
Jackie has appeared in a number of her husband’s movies, including Little Nicky, Bedtime Stories and That’s My Boy. In Hotel Transylvania, she voiced Martha, the wife of Sandler’s Dracula. Now, she also makes an appearance in Happy Gilmore 2, alongside their two daughters.
“Jackie and I like spending time with each other. We try to make each other laugh, try to listen, try to include each other, try to support each other,” Sandler told AARP in 2022.
He continued, “We try our best — that’s all. And we don’t ever think of not being together. We always talk about our future together.”
Julie Bowen attends the “Happy Gilmore 2” Premiere on July 21, 2025 in New York City. TheStewartofNY/Getty
Bowen, who plays golf tour public relations director Virginia, is single in real life.
Bowen was previously married to Scott Phillips from 2004 to 2018. They share three sons: Oliver, born in April 2007, and twins John and Gustav, born in May 2009.
In 2023, Bowen told PEOPLE that she wasn’t dating anybody new. However, she has remained on good terms with Phillips, who joined her in celebrating Oliver’s graduation from high school in June 2025.
Lupe McDonald and Christopher McDonald attend the “Fountain of Youth” premiere on May 19, 2025 in New York City. Dimitrios Kambouris/Getty
McDonald plays Shooter McGavin, a successful but arrogant golfer and the main antagonist of the movies. In May 2025, he told PEOPLE that Sandler and Netflix had “outdone themselves” with the sequel.
In his personal life, McDonald has been married for over three decades.
The actor met actress Lupe McDonald in 1989 when they performed in a theater production together. They got married in 1992 and share three daughters and a son.
Benny Safdie and Ava Safdie attend the 2024 New York Film Critics Circle Awards on January 03, 2024 in New York City. Cindy Ord/Getty
Filmmaker and actor Safdie didn’t appear in the first movie, and his new role could only be described as “juicy,” Sandler told IndieWire in August 2024.
Safdie, who was known for directing movies alongside his brother Josh until they split professionally in 2023 and has starred in movies like Licorice Pizza and Oppenheimer, married Ava Safdie in 2013. They share two sons, Cosmo and Murray, whom they keep out of the public eye.
“It’s been three years since I smashed that glass so hard I almost broke my foot!” Safide wrote on Instagram in honor of their three-year wedding anniversary in 2016. “I love you @avafrancis and the wild ride we’re on.”
Bad Bunny attends the “Happy Gilmore 2” Premiere on July 21, 2025 in New York City. Arturo Holmes/WireImage
Singer and rapper Bad Bunny, like Safdie, didn’t appear in the 1996 movie. Now, he plays Oscar, Gilmore’s caddy, in the sequel.
Bad Bunny met Gabriela Berlingeri in 2017, and they dated until 2022. The following year, he began dating Kendall Jenner.
At the end of 2023, they broke up, before they got back together in May 2024. However, the status of their relationship now remains unclear.
Ben Stiller and Christine Taylor attend PaleyFest LA screening of the season finale of “Severance” on March 21, 2025 in Hollywood, California. LISA O’CONNOR/AFP via Getty
Ben Stiller appeared in the first movie, though his role as abusive orderly Hal L. was uncredited. He then played the same character in Sandler’s 2020 movie Hubie Halloween and has brought Hal back for Happy Gilmore 2.
Stiller met his wife, Christine Taylor, in 1999, and they got married in May 2000. They separated in 2017, but reconciled after living together during the COVID-19 lockdown.
They share two children. Their daughter, Ella, was born in 2002, and their son, Quinlin, was born in 2005. Ella graduated from the Juilliard School in New York City with a degree in acting in 2024.
Stiller and Taylor have appeared alongside each other in the movies Zoolander, Zoolander 2, Dodgeball: A True Underdog Story and Tropic Thunder.
Sharon Dugan and Dennis Dugan attend the “Grown Ups 2” Premiere on July 10, 2013 in New York City. Stephen Lovekin/Getty
Dugan reprises his role as pro golf tour commissioner Doug Thompson in Happy Gilmore 2. However, he’s not directing the sequel as he did the first time around.
Dugan is married to Sharon O’Connor. In 2009, Dugan’s son Kelly was drafted by the Philadelphia Phillies in the MLB draft.
Kevin Nealon and Susan Yeagley attend the SAG-AFTRA Foundation Conversations on April 30, 2025 in Los Angeles, California. Amanda Edwards/Getty
Nealon played Gary Potter, an eccentric pro golfer and Gilmore’s partner at the AT&T Open, in the first movie, and he’s back for the second.
On Sept. 3, 2005, he married actress Susan Yeagley in Italy. “We’re going to follow the Italian tradition of having a huge bottle of wine,” Nealon told PEOPLE after their nuptials.
The two share a son, Gable, who was born in 2007.
“Having a baby with a comedian husband is an experience,” Yeagley told PEOPLE shortly after Gable was born. “Marrying a man [17 years older] is the best secret out there. He’s been around; he’s seen a lot. He’s committed to marriage and parenting, and it’s a blast.”
Kym Whitley attends the “Tyler Perry’s Straw” Screening on June 03, 2025 in New York City. Jamie McCarthy/Getty
Kym Whitley plays Bessie, Happy’s friend in Happy Gilmore 2. While she appears to be single in real life, she’s focused on raising her son Joshua, whom she adopted in 2011.
Travis Kelce celebrates with Taylor Swift after the AFC Championship Game on January 28, 2024 in Baltimore, Maryland. Patrick Smith/Getty
Kansas City Chiefs tight end Travis Kelce has a role in Happy Gilmore 2, with McDonald describing him to PEOPLE in June 2025 as a “surprisingly good” actor. For his part, Kelce described working with Sandler as a “dream come true” in a January episode of The Pat McAfee Show and said he was “every bit as cool off the screen”.
Kelce has been dating singer Taylor Swift since 2023. They went public with their relationship that October, and he’s since joined Swift onstage during her Eras Tour, while the popstar has rooted for him at his games.
“Her work ethic, what I saw on that tour last year, was pretty remarkable,” Kelce told reporters, including PEOPLE, of his girlfriend in February 2025. “I mean, to see the week in, week out traveling from one country to the next.”
Jack Antonoff and Margaret Qualley at The 67th Annual Grammy Awards on February 2, 2025 in Los Angeles, California. Phil McCarten/CBS via Getty
Qualley, who was born two years before the original came out, appears in Happy Gilmore 2.
In real life, Qualley has been married to musician and producer Jack Antonoff since August 2023.
She shared during an appearance on The Tonight Show Starring Jimmy Fallon in September 2024 that it was her husband who helped her land the role with a white lie.
When Sandler messaged Antonoff asking if Qualley played golf, he said that she was good — when she didn’t actually play. Qualley joked Antonoff “lied for the sake of the family.”
