Photographer Heather Jae's ex-husband proposing to his new fiancée. Credit : Notrealheatherjae/Instagram; Realheatherjae/Tiktok

Mom Helps Ex-Husband Propose to His Girlfriend to Teach Their Kids an ‘Important’ Lesson About ‘Love and Respect’

Thomas Smith
5 Min Read

When Derek Silver planned a surprise proposal for his girlfriend, he turned to someone unexpected for help: his ex-wife, Heather.

Heather, a photographer who goes by Heather Jae online, worked with Derek to set up a fake photo shoot for his girlfriend, Kaylin Drumeller, on a rooftop in Virginia, according to Today.com.

“I lost all of my business accounts, so I asked them to ‘model’ for me,” Heather explained in a TikTok video of the shoot and surprise proposal. The clip was shared online with the text: “Photographing my baby dad’s proposal to his gf.”

Kaylin Drumeller and Derek Silver photographed by Heather Jae. Notrealheatherjae/Instagram; Realheatherjae/Tiktok

The video, which now has more than 460,000 views and nearly 70,000 comments since being posted on Aug. 27, shows Heather taking photos of Derek and Kaylin before Derek suddenly kneels down and proposes.

According to Today.com, Heather’s wife, Meg, also helped by holding Derek and Kaylin’s infant son during the shoot while recording the moment.

Heather and Derek were together for seven years before marrying in 2020. They divorced less than a year later but remain close co-parents to their two children, ages 7 and 9.

“We don’t even really use the word ‘ex.’ We’re just the parents of our kids, and that’s what matters,” Heather told PEOPLE.

Heather said she agreed to help with the proposal because of what it would show their children. “It was important for me to be part of this moment because it showed how far we’ve come as co-parents,” she told Today.com. “Being there meant supporting something joyful in Derek’s life and showing our children that love and respect can still exist after divorce.”

Derek agreed, saying, “This is the relationship and family dynamic that we created.” He added that he sees Heather not just as an ex-wife, but as a sister and the mother of his kids. “We’re surrounded by a lot of love.”

Derek met Kaylin in 2023, and the couple welcomed their son six months ago. Over time, Kaylin and Heather have also become close friends.

Kaylin Drumeller and Derek Silver photographed by Heather Jae. Notrealheatherjae/Instagram; Realheatherjae/Tiktok

Still, Derek admitted their blended family dynamic wasn’t always easy. “It did not start out this way — it was very messy,” he said. “We were on a really bad path. I remember telling Heather, ‘We’re family for life — no matter what, we’re in each other’s lives, so we need to find a common ground.’ ”

Heather recalled a breaking point when she and Derek got into “a stupid argument” in a group chat where “things got misconstrued.” That was when, she told Today.com, “we realized, ‘This isn’t working.’ ”

Kaylin said they’ve since learned how important communication is. “We have different personalities, and it can be hard to understand where someone is coming from,” she explained. “Now, if something isn’t coming across the way we want it to, we get on a phone call … to better understand each other and not fight.”

Heather says she is genuinely happy for Derek and Kaylin. “I’m happy for both of them, and I love that I get to call Kaylin a friend, too,” she told PEOPLE.

Kaylin Drumeller and Derek Silver photographed by Heather Jae. Notrealheatherjae/Instagram; Realheatherjae/Tiktok

Heather’s video of the proposal quickly went viral, with many viewers praising the family’s dynamic. One person wrote, “This is what maturity and healing look like,” while another said, “That’s the definition of healed.”

While Derek and Kaylin haven’t set a wedding date yet, they plan to include everyone in their blended family. They see the wedding as another chance to show their children the value of unity.

“We all grew up in divided households, and it’s important for us that our children see unity amongst both households,” Meg told Today.com. Derek added: “You never want your kids to feel like they have to choose which parent they like more or which parent they want to be with. Our kids never have to think that way.”

“More than anything, I’m glad our children get to grow up seeing that you can still care about and support one another even if you’re not together anymore,” Heather told PEOPLE.

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