The 24-year-old and mystery man appeared to get along fabulously, chatting amongst each other as they strolled through the streets of Los Angeles, California, on Tuesday.
While some speculate a romance could be brewing, others are convinced the eldest daughter of former President Barack Obama may have just been enjoying a friendly outing.
She could be seen sipping on a smoothie as they spent time together in photos published by Daily Mail on Wednesday.
Malia was effortlessly chic in a pair of mom jeans and an oversized hoodie while the mystery man was clad in a black sweatshirt and baggy trousers.
Their latest hangout came days after cameras spotted the pair together. On July 28, the college grad and her counterpart were caught grabbing takeout food.
These days, Malia is keeping busy working as a screenwriter on Donald Glover's upcoming Amazon show.
At the time, Sasha and Malia's mother opened up about how both of her daughters are all grown up during an appearance on The Ellen DeGeneres Show.
Michelle gushed that her girls are "doing well" on their own, but are also "just amazing young women."
"They loved the Jonas Brothers. Now they are bringing grown men home," the Becoming author said. "Before it was just, like, pop bands. Now they have boyfriends and real lives."
As for Sasha, she is dating Clifton Powell Jr., 24, who is the son of Ray actor Clifton Powell.
In June, the actor dished about his son's budding romance and said he gave Clifton some pointers in the love department.
"You know that they've been going out for about a year, and it just hit the press, right?" said the star, 66, during a candid appearance on the Dear Fathers podcast.
"It has helped me talk to Clifton about how to handle Sasha Obama because we love the Obamas," he added. "I have an opportunity and a responsibility to make my son responsible, gentle, kind, loving, and supportive."