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Jenna Bush Hager played matchmaker with TODAY executive and her now-fiancé

Jenna helped set up TODAY senior vice president Libby Leist and her boyfriend, Sayan Ray, who proposed to her on Sunday with some help from Willie Geist.

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

Jenna shared on TODAY with Hoda & Jenna on Tuesday that she was the one who paired up Libby Leist, the senior vice president of TODAY and NBC News, and her fiancé, Sayan Ray, who had a sweet engagement during Sunday's New York City Marathon thanks to a little help from another TODAY host — Willie Geist.


Jenna was overjoyed to see her matchmaking efforts pay off after TODAY senior vice president Libby Leist and boyfriend Sayan Ray got engaged on Sunday.
Jenna was overjoyed to see her matchmaking efforts pay off after TODAY senior vice president Libby Leist and boyfriend Sayan Ray got engaged on Sunday.TODAY/@emilyfisherphoto

"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.

"Noah (Oppenheim), who’s our boss, said I just have to set up two more and then I can go straight to heaven. 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 in Sunday's 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 Sayan that contained the engagement ring. Willie also knows Sayan 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 Sayan then took a walk to the park that was the site of their first date. Sayan 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 Tuesday. "Everyone is Team Libby Engagement, and it’s so exciting."

Hoda celebrated Libby's engagement with a sweet message on Instagram.
Hoda celebrated Libby's engagement with a sweet message on Instagram. hodakotb/Instagram

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

"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."