Jenna Bush Hager’s College Romance Ruined Once She Lent Her Jeans to a 'Skinny Fella': 'I Can't Be Bigger Than You'

Jenna Bush Hager had one important rule when dating in college: no sharing clothes with boyfriends.

During the Thursday, October 9, episode of TODAY With Jenna & Friends, the talk show host, 43, looked back on an awkward wardrobe moment with an ex that eventually led to a breakup.

"I was dating a skinny fella. Getting ready for class, he put on my jeans, and they fit," she remembered. "And that was the beginning of the end...I was like, 'Oh, I can't be bigger than you.'"

Likewise, on Thursday morning, guest co-host Willie Geist accidentally put on a pair of his wife's pants.

"I was going to wear blue jeans with these. I reach into my bag...you run out of the house, sometimes you wake up early. It's dark. I was trying to get them on, and I'm like, 'Did I just wash these? They fit really tight,'" he explained. "And I realized they were Christina's flare jeans. I was trying to get into Christina's little flare jeans, and they're about eight sizes smaller than mine, and they pop out. They're cool at the bottom. Couldn't even get one leg in the top of it."

This is not the first time Jenna has reflected on past dating experiences on her talk show. During the Thursday, August 21, episode of TODAY With Jenna & Friends, she exposed a hilarious habit she employed while having boys sleep over at her house.

"Back in the early aughts, when I dated, I remember waking up early to brush my teeth," she recounted, then breathed at the camera. "This is how my breath smells upon first wake."

"You mean after a sleepover?" guest co-host Savannah Guthrie asked.

"Maybe," Bush Hager smiled.

Just two days prior, she recalled having "a couple of boys drop by" George W. Bush's mansion when she was younger to take her rollerblading to 7/11. There was no "smoochie" ever involved in her early dates.

Jenna is currently married to Henry Hager, with whom she shares three children: Mila, 12, Poppy, 10, and Hal, 6. She recently admitted she would consider expanding her family.

"I would have had 22 children...not 22," she said, correcting herself. "I had three, which feels like 21. I would have had one more. I would have rounded that out."

"It's never too late, though!" co-host Justin Sylvester maintained.

"Yeah, it's probably too late. It feels like that ship has sailed," Jenna expressed.