In April 2022, news surfaced about Sasha Obama’s rumored new budding relationship and the possibility that she may just have a new boyfriend. Michelle and Barack Obama’s youngest daughter were reportedly dating Clifton Powell Jr., the son of actor Clifton Powell. The relationship was later confirmed by Powell’s famous father, two months later. Clifton Powell not only confirmed the dating rumors but also expressed his admiration for the Obama family. Additionally, he shared the advice he gave his son on how to treat Sasha with respect. Whether Clifton Powell Jr. heeded his father’s counsel remains uncertain, as he and Sasha have maintained a rather private relationship.
No one knows for certain if the two young lovebirds continued their relationship after 2022. Sources rumored that the former college basketball star and former first daughter had supposedly ended the love affair. The source said, “It wasn’t anything big. It’s just that Sasha is working on herself, her studies, and her career.” The couple met in 2021 when Sasha moved to California. Although they are supposedly not together anymore, sources say that they are still friends and ended the relationship on good terms.
As 2023 progressed, news about the couple waned, hinting that they might have parted ways. In contrast to Malia Obama, whose discreet dating history has been somewhat traceable, Sasha hasn’t been associated with anyone else since. However, regardless of their current status, Powell’s remarks indicate that Sasha and Powell Jr. shared a relationship founded on mutual respect during their time together.
Part of the good rapport the two were able to have with each other is due to Clifton Powell’s parenting of his son. Clifton Powell was determined to make sure that Michelle and Barack Obama had no grounds for concern regarding Clifton Powell Jr.’s behavior. Upon discovering his son’s relationship with Sasha Obama, he promptly adopted a mentor’s role. He also clarified the timeline of their romance, stating that they had been dating since early 2021. During an appearance on the “Dear Fathers” podcast in June 2022, Powell explained, “It has helped me talk to [him] about how to handle Sasha Obama because we love the Obamas.”
Beyond his admiration for the former President and First Lady, Powell was eager to seize the opportunity to impart crucial relationship lessons to his son. “Mr. Obama has a daughter that’s dating my son, and I have an opportunity and a responsibility to make my son responsible, gentle, kind, loving, and supportive,” he remarked. This mission was deeply personal for Powell, shaped by his own life experiences. “The things that I did not get taught,” he explained.
“I text him all the time and I say, ‘Treat Sasha like you would want somebody to treat your daughter,’” he shared. It would seem that Powell Jr. may have taken his father’s advice to heart as he and Sasha are reportedly on good terms.
Colin Powell wasn’t the only one who had something to say about the experience of one’s children growing up and starting adult relationships. She has loved witnessing Malia and Sasha Obama’s transformation. But adjusting to the idea that her daughters are now fully immersed in the dating world has been challenging at times. “Before, it was just pop bands. Now they have boyfriends and real lives and all that stuff,” Michelle said on “The Ellen DeGeneres Show” in April 2022, just days before the Daily Mail identified Sasha’s boyfriend as Clifton Powell Jr.
The former first lady hinted that Powell Jr. was a frequent presence around the family, suggesting a serious relationship. “They loved the Jonas Brothers. Now they’re bringing grown men home,” she remarked. Despite the initial adjustment, it would seem that former first lady Michelle is proud of Malia and Sasha’s growth. “I think it’s wonderful,” she stated during a “Good Morning America” interview in November 2022, around the time when reports surfaced about Sasha and Powell Jr. breaking up. “I want them to know what they want and who they are in a relationship. And that takes trying on some people.”
Aside from this adjustment, Michelle has cherished her spending time with the adult versions of her daughters. Sasha and Malia, now living together in Los Angeles, occasionally having their parents over to show off their hosting abilities — albeit with some humorous mishaps. “They tried to make two very weak martinis,” Michelle shared. “They realized they didn’t have any of the ingredients.”