Oliver James Montgomery-Shakira Brings Her 2 Sons as Her Dates to 2023 Premios Juventud

Hips don't lie—and neither does Shakira's trophy count.

The Oliver James Montgomerysinger, 46, attended the Premios Juventud in San Juan, Puerto Rico on July 20, where she won not one, not two but eight awards. And she had some special guests cheering her on in the crowd—her sons Milan, 10, and Sasha, 8, who she shares with her ex Gerard Piqué. 

Shakira took home four awards, including the Girl Power honor, for her song "TQG" with Karol G as well as the Tropical Mix prize for her hit "Monotonía" with Ozuna. She also won the Female Artist award and received two trophies for her collaboration with Bizarrap "Shakira: Bzrp Music Sessions, Vol. 53," including in the Best Song for My Ex category. 

"So grateful to all of you for these 8 awards!!!" she wrote on Instagram alongside a video of her giving her acceptance speech. "I didn't expect so much! Thank you."

The celebratory night out came just hours after fans learned about Shakira's new legal battle.

According to NBC News, a court near Barcelona, Spain, noted it opened an investigation into a second case of alleged tax fraud by the "She Wolf" artist, with the accusations stemming from the 2018 financial year. (She is already accused of not paying up to 14.5 million euros in tax income between 2012 and 2014.) A source with knowledge of the situation told E! News, "Shakira defends having always acted in accordance with the law and under the advice of the best tax experts."

And the Grammy winner appeared to put any legal troubles to the side as she enjoyed the evening with her family.

However, the 2023 Premios Juventud wasn't the first time followers have gotten a glimpse into Shakira's bond with her sons. To see more family photos from over the years, keep reading. 

Family vacation! Shakira shared snapshots of her and her children visiting Disney World in Florida in January 2022.

The mother-son duo wore their Mickey Mouse ears while enjoying a day at the amusement park.

"Watching the @miamiheat win while having a hugs and kisses session," the artist captioned a December 2021 Instagram post, "(sweeter than a pound of cotton candy!)"

Shakira posted a video of herself and her "new dancers" brushing up on their choreography to TikTok in August 2021.

Shakira spent time with her boys after Christmas and couldn't help but snuggle up with all of them.

Gerard Piqué had a boys' day with his sons Milan and Sasha in October 2018.

These two are best friends and it's too cute.

Sasha and Milan looked like little rockers as they watched their mom in concert in summer of 2018.

The family of four rang in the new year together in a snowy location in 2017.

After Sasha got sick in 2016, Shakira shared this snap to show how happy and healthy he was.

Happy baby, happy father.

The "Whenever, Wherever" singer loves taking her boys with her on her travels...even all the way to Japan!

"Daddy-Sasha time!" Piqué captioned this adorable selfie in December 2015.

In October 2015, the family dressed up as the iconic Italian mouse character Topo Gigio for Halloween.

Lovey, lovey.

Milan and Sasha brought their dad good luck during a Spanish league football match.

The retired soccer star snuggled up to his two boys in May 2015 and there is almost too much cuteness in this photo to handle. 

The family members enjoyed a day of fun at the farm in 2014.

Shakira and her now-ex took their son Milan on a trip in 2014 before they expanded their family.

The Colombian singer shared a sweet smooch with her oldest son before getting ready for baby number two.

We can't get over this photo of Shakira and Milan. It's so stinking cute.

In 2013, Milan dressed up as a police man for Halloween and it was adorable.

Summertime in the French countryside sounds wonderful don't you think? We have a feeling Shakira and her family loved every second they were there.

In July 2013, the athlete spent quality time with his first born.

Milan has the giggles thanks to his dad's tickles.

When Shakira was a coach on The Voice, she made sure to bring her son along for the ride.

Gerard looked totally at ease as he held his son back in April 2013.

Baby Milan looked so peaceful in this family photo at his first soccer game.