Brenda Song Gushes Over Macaulay Culkin During Rare Red Carpet Date Night
Cupid got a little help in the matchmaking department thanks to Ciara and Russell Wilson.
After all, the “1, 2 Step” singer and the New York Giants quarterback set up Normani and DK Metcalf, who announced their engagement in March.
“@Russell Wilson and I knew when we introed yall 3yrs ago ..love was truly in the air!” Ciara captioned a March 14 TikTok video that showed the former Fifth Harmony member and the Pittsburgh Steelers wide receiver FaceTiming her and Russell and flashing the ring. “Now yall gon be booed up for forever!! This was the best news! @DK Metcalf @Normani we love yall so much!”
And they’re not the only stars responsible for a love connection. Brenda Song met fiancé Macaulay Culkin in 2014 through her Dads costar Seth Green. Although, it wasn’t exactly love at first sight.
“He was trying to be funny about our show being canceled and I was not having it,” The Suite Life of Zack & Cody alum told Cosmopolitan in January, with the Home Alone star admitting, “She was thoroughly unimpressed by me is what I will say.”
But fate—and Seth—gave them a second chance when they reconnected in Thailand three years later for Seth’s movie Changeland. Looking for something casual, Brenda took her friend’s advice: “If you’re going to ever have a fling,” she remembered her pal saying, “Mack is a safe person.”
And that fling is still going strong as Brenda and Macaulay are now parents to sons Dakota, 4, and Carson, 2.
Plus, Rita Ora has unmasked Robert Pattinson as the one who introduced her to her husband Taika Waititi—with the meet-cute turning into a yearslong friendship before The Masked Singer panelist and the director started dating in 2021.
Who else has taken a shot with Cupid’s bow and hit a perfect target? Read on to see more stars who’ve set up their celebrity pals.
Todd Owyoung/NBC via Getty Images, Leon Bennett/Getty Images, Rick Rycroft-Pool/Getty Images
Ed Sheeran, Isla Fisher and Sacha Baron Cohen Set Up Courteney Cox and Johnny McDaid
If we’re thinking out loud, then we’d have to add Ed Sheeran to our list of celebrity matchmakers. After all, the singer connected Courteney Cox with Johnny McDaid during a, um, casual night with friends in 2013.
“What happened was Ed said, ‘Can I have some friends over this weekend? ‘I said, ‘Of course,'” the Friends star said on a 2022 episode of The Howard Stern Show. “And he invited Johnny, Gary Lightbody—both of them from Snow Patrol—Taylor Swift, just some great musicians, and they all came over. And I had a fun group anyway. It was Sacha Baron Cohen and Isla Fisher, and Jennifer [Aniston] was there.”
In fact, it was now exes Isla and Sacha who really broke the ice.
“Isla went up to Sacha and said, ‘Sacha, Courteney wants to go out with Johnny,'” Courteney continued. “So, Sacha walks up to Gary and Johnny—and I’m going to cuss now—and says, ‘Hey, Courteney wants to f–k one of you from Snow Patrol, and it’s not you Gary.'”
Today, she and Johnny are still going strong.
Donato Sardella/Getty Images for REVOLVE
Nicole Richie and Joel Madden Introduced Cameron Diaz to Benji Madden
The story of how Cameron Diaz met husband Benji Madden is the sweetest thing—and it involves his brother Joel Madden and Nicole Richie.
“They didn’t set us up, but we were in the same room because of them,” the Charlie’s Angels star explained on a 2021 episode of Anna Faris Friends. “And then we found each other.”
Cameron and Benji found each other at a 2014 barbecue she was hosting and got engaged by the end of that year. The actress and the Good Charlotte band member tied the knot in 2015 and are now parents to daughter Raddix and son Cardinal.
TikTok / Ciara
Ciara and Russell Wilson Connected Normani With DK Metcalf
Celebrity matchmakers looking to level up may want to consult Ciara and Russell Wilson.
After all, the singer and the quarterback set up Normani and DK Metcalf, who announced their engagement in March 2025.
“@Russell Wilson and I knew when we introed yall 3yrs ago ..love was truly in the air!” Ciara wrote on TikTok alongside a screenshot of her and Russell FaceTiming the Fifth Harmony alum and the wide receiver as they showed off her engagement ring. “Now yall gon be booed up for forever!! This was the best news! @DK Metcalf @Normani we love yall so much!”
Francois Durand/Getty Images
Robert Pattinson Introduced Rita Ora to Taika Waititi
Rita Ora and Taika Waititi can thank Robert Pattinson for the dawn of their relationship.
“He’s a very good friend of mine,” she said about the Twilight alum on a March 2025 episode of The Masked Singer. “He actually introduced me to my husband.”
As the “How We Do (Party)” singer and the Jojo Rabbit director explained to Vogue Australia, the meet-cute occurred at a barbecue Taika was hosting in L.A. that sparked a yearslong friendship before it turned romantic in 2021 and they wed the following year.
Jason Hanna/Getty Images, Jamie Squire/Getty Images, Roy Rochlin/Getty Images
Patrick Mahomes and Erin Andrews Played Matchmaker for Taylor Swift and Travis Kelce
Patrick Mahomes isn’t going to shake off the role he played in Taylor Swift and Travis Kelce‘s romance.
“I like to take some of the credit,” the Chiefs quarterback said on a May 2024 episode of The Pat McAfee Show. “I was the one who invited Travis to the first Taylor concert when the friendship bracelet was—he was sitting in my suite. So, I feel like I was the matchmaker. I had some input in there as well. I was like, ‘Dude, just go for it.'”
Still, Patrick wasn’t the only one cheering them on.
“There were definitely people she knew that knew who I was, in her corner [who said]: Yo! Did you know he was coming?” Travis told WSJ. Magazine in November 2023 months after the enchanting concert. “I had somebody playing Cupid.”
While there’s a blank space as to who he was referring to, fans have got a list of names and Erin Andrews‘ is in red underlined. Especially because the sports reporter and her podcast cohost Charissa Thompson encouraged Taylor to give Travis a chance on an August 2023 episode of their show—with Travis later writing on Instagram, “I owe you big time!!”
Amy Sussman/Getty Images, Olivia Wong/Getty Images
Seth Green Introduced Macaulay Culkin to Brenda Song
Brenda Song didn’t exactly have a suite, er, sweet impression of fiancé Macaulay Culkin when she met him in 2014 at the house of her Dads costar Seth Green.
However, they got another chance at love when they reunited in 2017 for Seth’s movie Changeland that was filmed in Thailand.“When we were there, Mack and I, we worked a total of 10 days, and we were there for six weeks and started hanging out. And I thought he was gonna be my BFF,” Brenda recalled on a March 2025 episode of The Drew Barrymore Show. “And I was like, ‘Oh wait, I kind of have a crush on him.’ And then I thought I was going to have my first fling, and that fling has turned into almost eight years and two kids.”
John Salangsang/BEI/Shutterstock, Dominik Bindl/WireImage
Chloë Grace Moretz Set Up Meghan Trainor and Daryl Sabara
When Meghan Trainor met Daryl Sabara in 2014, she didn’t know he’d become her dear future husband.
“I was 18 years old as a baby songwriter out here in L.A., and I was at a songwriter Hollywood party and he crashed it with two of his friends,” the “All About That Bass” singer said on a November 2022 episode of The Drew Barrymore Show. “And I was like, ‘Spy Kids is here!’ I went right to him. I usually fangirl so hard and I don’t say anything. But I went right to him and was like, ‘Are you Spy Kids?’ And he was like, ‘Yeah,’ and was really nice.'”
However, their paths crossed again two years later thanks to Chloë Grace Moretz.
“I was like, ‘I want a nice guy. I’m sick of all these mean guys. I want a nice guy,'” Meghan recalled. “And she’s like, ‘My best friend’s the nicest guy.'”
So, she and Daryl went on a double date with Chloë and then-boyfriend Brooklyn Beckham. And as Meghan, who wed the Spy Kids actor in 2018 and shares kids Riley and Barry with him, put it, “We’ve never been apart ever since.”
CHRIS DELMAS/AFP via Getty Images, Rodin Eckenroth/FilmMagic
Jensen Ackles Connected Hilarie Burton With Jeffrey Dean Morgan
Don’t want to be out of the loop on how Hilarie Burton met Jeffrey Dean Morgan? Well, it turns out Jensen Ackles—who worked with Jeffrey on Supernatural and whose wife Danneel Ackles appeared on One Tree Hill with Hilarie—set them up on a blind date in 2009.
“I happened to be single, and Jensen said, ‘I’ve got a girl you should meet,'” The Walking Dead star told HuffPost in 2015. “And so I went to a bar, and I met Hilarie at a bar with Jensen and Danneel.”
Afterwards, he continued, they went back to his house for some tequila (though Hilarie had to leave for North Carolina the next day).
“She was really cool,” Jeffrey added, going on to share how they stayed in touch. “I was on my way to do a movie called The Resident in New Mexico. She was on her way to Paris, and I talked her into, instead of going to Paris, come and see me in New Mexico.”
In 2010, the couple welcomed son Augustus, and daughter George came eight years later. Hilarie and Jeffrey, who live with their family on a farm in upstate New York, then wed in 2019.
For the latest breaking news updates, click here to download the E! News App
This story was originally published March 30, 2025 at 3:00 a.m. PST.
Leave a comment