Glen Powell Details Reuniting With Sydney Sweeney at His Sister's Wedding
Glen Powell is reflecting on a special family milestone.
The actor—who sparked dating speculation last month when he attended his sister Leslie Powell’s wedding alongside his Anyone But You costar Sydney Sweeney—penned a touching message to the bride and her new husband Thomas Gillespie on social media following the occasion, affectionately referring to his sibling as “Mrs. Lil Sis.”
“Leslie and Thomas, you’ve beaten the odds,” he wrote in a post on Instagram April 17. “You’ve found goodness, you’ve found goofiness, and most importantly, you’ve found each other.”
Alongside a collection of photos from the special day, Glen, 36, added, “I couldn’t be happier for you both…”
Glen and Sydney’s reunion at the Texas nuptials—coupled with her recent breakup with fiancé Jonathan Davino—sparked renewed speculation of a romance between the two, whose on-and-offscreen chemistry caught fans’ attention amid the release of the 2023 romantic comedy.
But days after the wedding, the Top Gun: Maverick star laughed off the rumors when asked about the situation.
“Timing is everything in this world, isn’t it?” he said on the April 2 episode of Jenna & Friends, noting that Sydney and Leslie “are obviously great friends.”
“It was a hell of a wedding,” he continued. “The Powells know how to do it right, so all the people that love her were there.”
Ethan Miller/Getty Images
Meanwhile, Glen’s mom Cyndy Powell addressed the chatter more directly, telling the Daily Mail March 31, “They’re definitely not together.”
The matriarch noted that Sydney, 27, attended the wedding “with a friend” and described the notion of her and Glen dating as “silly.”
“We love Sydney,” Cyndy explained. “We’ve considered her just a really, really good friend. We were all together so much and we haven’t seen her in a long time. She’s really a friend and we all enjoy her.”
For a closer look at Sydney’s relationship timeline with Jonathan Davino, keep reading.
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September 2018: First Dates
Euphoria actress Sydney Sweeney and businessman Jonathan Davino first sparked dating rumors in 2018 when they were spotted attending several parties together, including Hulu's Emmy Party in Los Angeles.
Charley Gallay/Getty Images for InStyle
October 2018: Party People
The pair were photographed at the InStyle and Kate Spade dinner in Beverly Hills.
James Devaney/Getty Images
October 2019: Game On
A year later, the Anyone But You star and her guy enjoyed a night out at a New York Knicks game in NYC.
BACKGRID
February 2022: Bargain Hunting
The private pair enjoyed a low key trip to the flea market in West Hollywood weeks before they got engaged.
"I don’t date people in the spotlight," Sydney explained to Cosmopolitan of her stance on romance in 2022. "I don't date actors or musicians or anyone in entertainment because I can just be normal Syd that way and it's easiest."
When asked about what she looks for in a partner, Sydney explained: "I look for a best friend. I need to be able to be with someone who I can literally hang out with 24/7 and never get sick of and we laugh every single day."
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May 2023: Stepping Out
The White Lotus actress and her fiance continued their adventures with a fashionable trip to the Cannes Film Festival in 2023.
Billy Rosewood / SplashNews.com
September 2023: Back in Black
Looking all loved up in matching black outfits, the cute couple attended an event at the Venice Film Festival in Italy.
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March 2024: Happy Family
Back in New York City, the twosome were spotted walking Sydney's dog Tank.
Aissaoui Nacer / BACKGRID
July 2024: Sydney in Paris
The power couple, who produced Anyone But You and Immaculate together, held hands after a romantic dinner in Paris.
As for what it was like to mix work and romance? Sydney told Glamour UK in 2023, "It’s really great to work with someone who knows you so well, who fully supports your ideas, your vision and your voice."
Aissaoui Nacer / BACKGRID
September 2024: Workaholics
The couple returned to the Venice Film Festival in 2024, with Sydney telling Entertainment Tonight months earlier that they hadn't started any wedding planning, noting, "I am so busy working!"
TheStewartofNY/GC Images
January 2025: Snowball Fight
During a rare outing in winter 2025, the couple partook in a cheeky snowball fight in New York.
Victor Boyko/Getty Images for Miu Miu
March 2025: Separate Ways
In March 2025, multiple outlets reported that Sydney and Jonathan had called off their engagement and relationship after seven years together.
Just before their breakup was confirmed, Sydney attended a wedding alongside Glen Powell—who she first sparked romance rumors with amid press for Anyone But You in 2023—in Texas. However, Glen's mother Cyndy Powell, shut down any romance brewing, telling the Daily Mail in 2025 that Sydney is simply a "friend" of the Powell family.
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