Jenna reveals her method for ‘hooking people up’ on dates

In between working for TODAY, raising three children and running a popular book club, Jenna Bush Hager is also apparently a part-time matchmaker.

She’s revealing the method behind her matchmaking strategy that landed Libby Leist, the senior vice president of TODAY and NBC News, her now-fiancé, Sayan Ray. He staged a sweet engagement in 2021 during the New York City Marathon thanks to a little help from another TODAY host, Willie Geist.

“OK, so here’s what you do,” the Bush Hager said on TODAY with Hoda & Jenna March 22.

You have to connect with people outside of your circle, Jenna said, otherwise, “you end up asking the same people.”

“So with Libby, I texted three people, my sister who is in graduate school, our one friend who had just moved to Connecticut so had a whole, new different world and another friend that had just moved out of the city, too. And guess what? One of the friends had somebody,” Jenna said.

This isn’t the first time Jenna has spoken about her matchmaking skills. She previously spoke about it on TODAY in 2021.

“It’s really exciting, and I’m just going to go ahead and say it — I set them up,” Jenna said. “I set that couple up, that’s the couple we’ve been talking about.”

Jenna then referenced an awards event honoring Hoda Kotb the TODAY family attended the previous night, during which then-president of NBC News Noah Oppenheim joked about Jenna playing cupid.

“(He) said I just have to set up two more and then I can go straight to heaven,” Jenna recalled. “So last night instead of hanging out with Hoda, I said to Noah, ‘Should I just make an announcement and say, ‘Single people, come my way?’”

Jenna also shared some of the backstory on the engagement, which involved some stealth work from Willie while he was running the New York City Marathon.

“Their engagement story is the cutest,” she said.

At one point in the race, Willie ran up and hugged his sister and Libby while quickly handing off a Dunkin’ Donuts bag to Ray that contained the engagement ring. Willie also knows Ray well, as they share a close mutual friend.

Willie had been running a couple of miles while carrying the bag to help set up the surprise, according to Jenna.

Libby and Ray then took a walk to the park that was the site of their first date. Ray got down on one knee and proposed as a friend grabbed some shots of the sweet moment while hiding in the nearby bushes.

The news then spread quickly among the TODAY family.

“Noah said that his wife physically screamed in joy when she found out Libby was engaged,” Hoda said. “Everyone is Team Libby Engagement, and it’s so exciting.”

For those who didn’t know, Hoda announced it by sharing a shot of pictures of her with Libby showing off her new ring on her Instagram stories.

“I don’t know if I was supposed to,” Hoda said. “I thought people knew! Anyway, I hope I didn’t mess anything up. Libby, we love you, congratulations.”

Jenna is also not done matchmaking. She and Hoda are asking fans to reach out so they can help with their love life as well.

“And maybe I’ll set you up on the show, and if I just get two more, I go to heaven,” Jenna said. “I mean, I hope I’m going to heaven anyway, but nothing’s guaranteed.”

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