How Macaulay Culkin Re-Proposed to Brenda Song With Help From Sons

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Macaulay Culkin ram, erm, ran into a slight issue when popping the question. 

Okay, so, you will NOT believe this! My husband, he’s 45, totally re-proposed to Brenda Song in August! It was the sweetest thing ever, and get this – Dakota, who’s five, and Carson, who’s four, helped him! My heart melted, seriously. They’re such a perfect little family, and this just proves it!

Brenda was on her way home from Running Point when her mom texted her, asking if she was wearing makeup. Brenda was surprised by the question, especially because when she got home, she found flowers by the door and her two sons waiting for her, as she shared with Kylie Kelce on her Not Gonna Lie podcast.

Although the Home Alone star had the proposal all planned out, things didn’t quite go as planned.

You won’t believe what happened to me the other day! I was walking somewhere and suddenly saw this person, and my first thought was, ‘Oh my gosh!’ They immediately looked at my sons and asked, basically, ‘What are you going to say to your mom?’ And my little one, without missing a beat, shouted ‘Ram’s House!’ It was the cutest thing!

Brenda is a devoted Los Angeles Rams fan, and she’s passed that passion on to her kids. She says they even practice Rams cheers at home!

She explained that she often does a playful call-and-response with her husband. She’ll ask, ‘Whose house is this?’ and he always replies, ‘Ram’s House!’ She jokingly said she’s taught her kids well, implying they’ve picked up on this fun tradition.

Macaulay shared that he and his fiancée practiced the proposal so much, they jokingly asked if she would marry them. Despite their son briefly changing the rehearsed lines, Brenda was thrilled he immediately recognized the location as ‘Ram’s House’.

Kylie, who shares four daughters – Wyatt, 6, Elliotte, 5, Bennett, 3, and Finnley, 12 months – with her ex-husband, Philadelphia Eagles player Jason Kelce, playfully responded, “That’s wonderful. I’m raising them well.”

Before recently renewing their vows, actor Macaulay Culkin proposed to Brenda Song in January 2022, shortly after they welcomed their first child. They quickly had a second child, and their two kids have been a part of all their special moments since, including Macaulay’s Hollywood Walk of Fame star ceremony in 2023.

Brenda explained to Bustle that a particular moment felt too important to share without her sons, even though they dislike being photographed. She said her son, Dak, was frightened by the cameras, which is a big reason why they generally try to keep their children out of the public eye. The boys simply didn’t understand what was going on.

Read on to see the sweetest moments between Mac and Brenda…

Macaulay Culkin and Brenda Song were on theme at Billie Lourd‘s 33rd birthday party in July 2025.

Brenda celebrated their eighth anniversary in June 2025 by sharing a heartwarming photo on Instagram. She wrote a sweet message expressing how much her partner makes her laugh, feel understood, and loved.

To my best friend, my partner in everything, and the father of my child – thank you. Being loved by you is the greatest gift.

Macaulay and Brenda were decked out in their favorite football team’s colors in 2024.

In March 2024, the couple made a rare public appearance together at a Clarins product launch event in Los Angeles.

The couple celebrated Brenda’s 36th birthday in Cabo San Lucas, Mexico, in 2024. 

Macaulay bought a t-shirt from the resort and then jokingly pretended to work there, offering Brenda a towel while she relaxed by the pool.

He also played bellhop and carried her bags, much to Brenda’s confusion and amusement.

I was so thrilled to see Macaulay Culkin finally get his star on the Hollywood Walk of Fame in December 2023! And it was even more special because he brought his son, Dakota, with him. It was a really heartwarming moment.

Macaulay and Brenda’s baby boy Carson also made an appearance at the ceremony.

The couple were all smiles at the family event.

In 2023, the Home Alone star got into the spooky season spirit as Brenda passed out candy.

The duo appeared at the GFS Fall Benefit in Santa Monica, Calif., in October 2023.

TopMob News reported in January 2022 that Brenda and Macaulay were engaged. The actress was seen with her engagement ring while out in Beverly Hills.

In 2020, Brenda wished everyone a ‘Hoppy Valentine’s Day’ on Instagram while celebrating the holiday with Macaulay in the water.

In 2018, while walking around the Friedrichshain neighborhood of Berlin, the couple showed affection by holding hands.

In 2022, Macaulay Culkin and Brenda Song celebrated their son Dakota’s first birthday with a trip to Sesame Place San Diego. Brenda shared a photo on Instagram of them with Elmo, calling the day “magical” and saying they “had so much fun!”

In 2020, Brenda wished Macaulay a happy 40th birthday on Instagram, calling him a ‘magical being.’ She wrote that she could go on and on about how amazing he is – how kind, loving, funny, and genuine – and how thankful she is to share her life with him. But she jokingly added that he’d probably never see it, since he doesn’t use Instagram. She finished by saying he’s like a ‘unicorn’ she never believed existed and that she feels incredibly lucky to be loved by him.

In April 2018, Brenda publicly showed her support for her boyfriend’s podcast, excitedly sharing that she had been a guest on it. She called it a fun experience with ‘my favorite bunny’ and ‘two of my favorite people,’ tagging the podcast account @bunnyearspodcast and her boyfriend, @mattbennett.

The famous couple showed their support for a good cause by attending the Stand Up To Cancer event in Los Angeles in 2018.

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2026-05-01 16:47