Posted by Emily Exton on 11/21/2012 at 3:33 PM Videos

The Popdust Files: justin bieber, oprah winfrey, Oprah's Next Chapter, television, TV Party

This weekend marks the beginning of playing holiday jams free of judgment and an inevitable, enjoyable weight gain, but it’s also the premiere of Justin Bieber’s sit-down interview with Dame Oprah on her Next Chapter series. We’ve gotten a look at what happened when the two joined forces to in Chicago to talk about all the great details that haven’t been revealed in multiple memoirs or video montages on the Believe tour. Doing what she does best, Oprah was able to unlock the the sweetest of sweet comments from deep within the 18-year-old which now seem extra poignant in retrospect. But if we know Oprah, there were probably some tears, too. Those must stay in, Bieber. That is how you let Selena know you truly care, not by waiting outside her house sans boom box.

When they weren’t shedding light on his hopes and dreams, the new pals were leaving the studio for a field trip to the rich, mahogany-paneled walls of Ralph Lauren. Oprah walks around like she owns the place—because she probably does—while the hired help leave their posts to shake the hand of the Bieb. Despite the perception that she knows you better than your mom and yourself, Oprah admits to handing out a handbag or a cashmere sweater when she’s at a loss for better ideas. Not bad by Bieber, particularly if it’s purple. Sadly he was unsuccessful in his quest to get Oprah to sport a pair of his favorite baggy/skinny drop-crotch sweats. Next time.

Picking up a RL speciality for Jaxon or Jazmyn is perfectly fine—Canadian winters can be brutal—but don’t think that Selena isn’t aware of what the great cashmere sweater signifies. Catch Justin Bieber on Oprah’s Next Chapter this Sunday, November 25, at 9 p.m. EST on OWN.