Bieber and Richie – who will celebrate her 18th birthday later this month – hung out in Laguna Beach and the singer's Toluca Lake house on August 10, going on a hike before jetting off to Japan, the insider says, where Bieber, 22, has two Purpose World Tour shows this weekend.
Richie shared a snap on board a private jet, writing: "No pictures please."
So who is the teenage Instagram star who calls Nicole Richie sister and has posed for Town & Country? Here's everything you need to know.
1. She was the face of Material Girl
Following in the footsteps of Zendaya, Rita Ora and more, Richie modeled for Madonna's juniors clothing line Material Girl last year.
Of the major career moment, Richie previously told WHO, "I am a Madonna obsessor since I was 5, so it's insane that this is happening."
Richie helped celebrate the brand's fifth anniversary by modeling the trendy clothes while snacking on sweets.
2. She's got a regular kid curfew
While posing for Nylon in late 2014, Richie revealed that despite a star-studded lifestyle, her father still insists she follows a curfew.
Richie is home-schooled during the day, but if she hangs out with friends at night, she's required to be home by 11 p.m.
"It's a generous curfew," she said at the time. "I have time to be a 16-year-old. And sometimes just being a kid is fun."
3. She once dreamed of being a teen pop star
Just four years ago, Richie envisioned a much different career path for herself: "When I was 13, I was saying that I wanted to be signed to a label," she told Entertainment Tonight.
"I was begging my dad to get me signed with somebody," she said, revealing that the "Hello" singer was most definitely not on board.
While at first heartbroken over the restriction, Richie is now "glad" the singer-songwriter held her off.
"I was determined that I was so ready, and I was in the perfect spot to do all these crazy things," she said. "But I just needed to grow up and learn about life and that wasn't going to be as easy I thought it was going to be."
What could have been, though? Richie revealed her songwriting process to Teen Vogue in 2012, explaining that she's written a few tunes by creating a rhythm, then freestyling to add in beats.
4. Nicole is her 'style icon'
When seeking fashion inspiration, Richie looks no further than her immediate family tree.
"Nicole is definitely my style icon, and she's the best person to go shopping with," she told Teen Vogue. "She's really honest. Other people are afraid to hurt your feelings, so they'll tell you something's cute when it isn't, but she'll be like, 'No, discard that.'"
Richie likes her big sister's style so much, she used to literally steal it. Richie told WHO last year, "When I was 15, I would steal clothes out of my sister's closet, like, all day."
The teen's style is a little different than Nicole's "hipper" look though: "I like to wear basic items, but I try to pick myself apart from people by adding in certain things like a cool jacket or some cute boots or a cool hairstyle."
5. She's obsessed with Tumblr
Want to see what looks Richie is vibing? Just head over to her personal Tumblr.
"I never really thought I would make a blog myself," she previously told WHO. "Then I got super interested in pictures and runways. I started following a bunch of model blogs and runway blogs and then I just started following designers. Sometimes I'll see something on Tumblr and think, 'Oh my God, how did I not think about this?' "
Richie's page is filled with editorial spreads, runway looks and lots of Rihanna street style snaps.
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