Justin Bieber Raises Eyebrows After Outing With Troubled Former Child Star
By Kelly Coffey-Behrens on May 22, 2025 at 7:15 PM EDT
Justin Bieber is making headlines once again, this time not just for his words, but for who he's been spotted with.
The pop superstar was seen visiting a bank this week alongside "That’s So Raven" alum Kyle Massey and his fiancée Hana Giraldo, the daughter of rock legend Pat Benatar.
The trio’s unexpected outing comes amid growing concern over Justin Bieber’s recent behavior and emotional social media posts.
Justin Bieber’s Connection To Kyle Massey
Bieber and Massey have a long history.
The two were first publicly linked back in 2015 when Bieber’s close friend Lil Twist was sentenced to a year in jail after breaking into Massey’s apartment and robbing his brother, Chris Massey, in a 2014 incident. Twist eventually pleaded no contest to six felony charges.
Over the years, Massey has spoken about Bieber’s influence on his music journey and has also connected through livestreams, chatting candidly about music, family, and life in the spotlight.
Check out the photos of Bieber and Massey's latest outing, courtesy of Daily Mail.
Kyle Massey’s Dark Past Resurfaces
Kyle Massey himself has also faced controversy.
In July 2021, he was charged with a felony for immoral communication with a minor after allegedly sending explicit material to a 13-year-old girl.
Prior to the criminal charges, the girl's mother filed a civil lawsuit in 2019 seeking $1.5 million, alleging Massey had sent explicit texts and images to her daughter. Massey denied the accusations, labeling them an extortion attempt, and stated the case was eventually dropped after the plaintiff’s legal team withdrew.
The case drew widespread media attention and significantly impacted Massey's public image.
"No child should ever be exposed to sexually explicit materials," Massey said in a statement through his attorney, Lee Hutton, at the time. "I unequivocally and categorically deny any alleged misconduct."
Justin Bieber Admits He Once Told Hailey She’d 'Never Be On Vogue'
The pair's sighting comes on the heels of Bieber's latest eyebrow-raising Instagram confession, where he opened up about a past argument with his wife, Hailey Bieber.
In the post, Justin recalled a heated moment when he told Hailey she would “never be on the cover of Vogue,” a remark he now regrets. “So mean,” he admitted. “For some reason, because I felt so disrespected, I thought I gotta get even.”
He later added that maturity has taught him the value of connection over retaliation, ending his message with a public apology to Hailey. “So baby, you already know, but forgive me for saying you wouldn’t get a Vogue cover because clearly I was sadly mistaken," he said.
Hailey Bieber Shuts Down Split Rumors
As rumors continue to swirl about her personal life and marriage to 31-year-old Justin Bieber, Hailey Bieber isn’t letting the noise get to her. In fact, she’s setting the record straight.
In her recent Vogue cover story, the model firmly shut down the breakup speculation, making it clear that the chatter is baseless.
"That's not real," she said bluntly, addressing the tabloid noise.
Hailey, who shares 9-month-old son Jack Blues Bieber with the pop star, added, "And that’s the thing: I have a real life. My real life is that I get to wake up to my beautiful family and my son and my friends, and I have people that know me and love me, and I love them."
Justin Bieber Grabs Crotch In Public Meltdown Over Parking Ticket
Adding another layer to Justin Bieber’s recent string of headline-making moments, the pop star sparked fresh controversy this week with his reaction to a parking ticket. What started as a minor infraction quickly escalated into a public spectacle on May 21, when Bieber was photographed making an obscene gesture after discovering the fine on his luxury vehicle.
The 31-year-old was seen exiting the First Credit Bank in Beverly Hills when he noticed the ticket on his Mercedes G-Wagon. Clearly irritated, Bieber responded by grabbing his crotch in protest, a move that some interpreted as a sign of growing frustration amid ongoing speculation about his personal life.
Sources revealed that the vehicle had been improperly parked in a commercial loading zone and was also missing a front license plate, which is required by law in California. The moment, while brief, did little to quiet concerns about Bieber’s current state of mind.
