Jazz Jennings Dishes On Making Barack Obama 'Proud' — and One Super Awkward Hug with Oprah Winfrey!

Jazz Jennings‘ meeting with former President Barack Obama was one for the books!
The 16-year-old I Am Jazz star opened up about her “incredible moment” with the 55-year-old, in which the beloved politician graced her with four words she’ll never forget. 

“We were at the White House for the pride reception,” Jennings recalled on Tuesday’s PEOPLE Now, noting that Obama began chatting with her during a quick stop for photos. “He started saying things like, ‘Oh, so you’re in high school now, how is that? How old are you? Oh, you’re the same age as my daughter.’ ” 

She added, “Everyone was kind of rushing him and as we were leaving he said, ‘I’m proud of ya.’ And it was just an incredible moment to hear the president say that he’s proud of you!” 

Not all of Jennings’ moments with the stars have unfolded quite as smoothly, though. The teen also recalled one super awkward moment she witness her mother share with Oprah Winfrey after an interview. 

“My mom, she wanted to meet Oprah as well — ’cause she’s Oprah,” the trans youth activist said. “And when she went in for the hug I don’t think Oprah was ready so my mom kind of just went in and it was like a single hug basically.” 

“She nestled her head on her breasts like a pillow!” Jennings added. 

The star wasn’t too embarrassed by the display, though: “It was fun. It was fun.” 

I Am Jazz returns with a two-night premiere on TLC on June 27 at 10 p.m. ET and June 28 at 9 p.m. ET. Jennings’ book, Being Jazz: My Life as a Transgender Teen. comes out June 27.