Remember when Malia and Sasha Obama were just those cute little girls moving into the White House with their parents? Well, times have definitely changed! The Obama sisters are all grown up now, living their best lives in Los Angeles, and their dating choices might surprise you. From British students to music producers and even the children of Hollywood stars, these former First Daughters have been making some interesting romantic connections that nobody saw coming when they were just kids in the White House.
The Secret Service became third wheels on Malia’s dates
Dating is awkward enough as a teenager, but can you imagine having trained government agents watching your every move? That was Malia Obama’s reality! As the daughter of the President, Malia had to navigate the already complicated world of teenage dating with Secret Service agents tagging along. Talk about pressure! These agents were there for her protection, but they definitely made for some unusual date settings. Any boy brave enough to ask her out knew they weren’t just impressing Malia – they had an audience of highly trained federal agents keeping tabs on their every move.
Malia somehow managed to handle this unusual dating situation with grace. While most teens worry about their parents embarrassing them, Malia had to deal with agents in dark suits and earpieces nearby. Despite these challenges, she still managed to have something resembling a normal dating life during her White House years. Michelle Obama has spoken about how proud she is of the way her daughters handled growing up in the public spotlight, describing them as “good, decent, normal young women who are trying to be impactful in the world.” The fact that Malia could navigate dating with such unusual circumstances speaks volumes about her character and ability to adapt to her unique situation.
Malia’s British boyfriend caught everyone by surprise
Malia Obama’s first serious relationship made headlines when she was spotted kissing Rory Farquharson at a Harvard-Yale football game in 2017. The British law student quickly became the subject of intense public interest – after all, it’s not every day that a foreign student dates a former First Daughter! Their relationship lasted several years, much longer than most college romances. The pair kept things relatively private, but they were occasionally spotted together, including on a romantic vacation in Europe. This wasn’t just some brief fling – by all accounts, Malia and Rory were together for around five years, from 2017 until around 2022.
What made this relationship particularly interesting was the international aspect. While many presidential children date within their social circles in Washington, Malia stepped outside that bubble completely. Rory wasn’t connected to American politics at all – he was just a regular (albeit wealthy) British student who happened to attend the same university as Malia. Their relationship survived through their college years, which is impressive considering how many college relationships fizzle out after a semester or two. Michelle Obama even mentioned in interviews that Rory had spent some time quarantining with the Obama family during the pandemic, suggesting he had been welcomed into their inner circle. Their lengthy relationship suggests this was much more than just a casual college romance.
Malia’s music industry connections raised eyebrows
After her relationship with Rory ended, Malia Obama’s dating choices took an interesting turn toward the creative world. In 2022, she was linked to Dawit Eklund, an Ethiopian music producer who’s nearly a decade older than her. The pair were spotted together multiple times in Los Angeles, sparking widespread speculation about their relationship. Eklund isn’t just any producer – he’s described as one of Washington D.C.’s “most exciting dance music producers” and co-founded his own record label in 2016. This connection made sense given Malia’s own creative interests and her work in the television industry, where she’s been pursuing her own career in writing and producing.
The age gap between Malia and Dawit raised some eyebrows, but Michelle Obama has mentioned that Barack has learned to be a “concerned Black father, but not crazy” about his daughters’ dating lives. More recently, Malia was seen grabbing sushi with rapper Aminé in late 2023, though it’s unclear if this was a romantic date or just a friendly meetup. Either way, Malia seems drawn to creative types in the music industry, which is a far cry from the political circles she grew up in. Her attraction to artists and producers shows her breaking away from her political family background and forging her own path in more creative spheres. These connections also reflect her reported love for music genres like hip-hop, R&B, and rock – interests she’s clearly pursuing in both her professional and personal life.
Sasha’s romance with a Hollywood kid made headlines
While Malia’s dating life has gotten more attention, younger sister Sasha has been making some interesting romantic choices of her own. After transferring from the University of Michigan to the University of Southern California, Sasha began dating Clifton Powell Jr., the son of actor Clifton Powell Sr. (known for his role in the movie “Ray”). This connection to Hollywood royalty marked a major shift for the youngest Obama, who had previously kept her dating life extremely private. Their relationship became public when they were spotted casually walking together, and unlike some of the speculation around Malia’s relationships, Clifton Powell Sr. has actually confirmed his son’s relationship with Sasha.
Clifton Powell Jr. (nicknamed “Cliff”) comes from an affluent Los Angeles family – his mother runs an interior design firm and catering company, while his father is an established actor. He was previously a college basketball player who earned a scholarship to the University of California, Santa Barbara, but left after less than a year to pursue other interests, including working on television commercials. Like Sasha, who’s forging her own path after growing up in the political spotlight, Cliff seems to be finding his way in creative industries despite having a famous parent. Before Cliff, Sasha was reportedly seen kissing a young man named Matt Metzler at a music festival, but her relationship with Powell appears to be more serious and long-lasting.
Michelle Obama spilled surprising details about their love lives
While the Obama sisters try to keep their relationships private, their mom has occasionally dropped some interesting tidbits about their dating lives. In interviews, Michelle Obama has revealed that both Malia and Sasha have been “bringing grown men home” and are actively “dating around” as young adults. This casual mention of “grown men” certainly caught people’s attention! It’s one thing to imagine the former First Daughters dating college classmates, but Michelle’s phrasing suggested something more mature. She’s also mentioned how the family dynamic has changed now that the girls are adults with “boyfriends and real lives,” a far cry from when they were just kids with crushes on pop bands during the White House years.
Michelle has also shared her parenting philosophy regarding her daughters’ love lives. She’s expressed hope that Malia and Sasha won’t rush into marriage, advising them to take their time and allow their relationships to remain “fluid and youthful.” This gives us a glimpse into how the Obama parents are handling their daughters’ transition into adult relationships. Michelle has also talked about how Barack has had to learn to be a “concerned Black father, but not crazy” about his daughters dating – a relatable comment for many parents watching their children grow up and start serious relationships. Despite the girls’ unusual upbringing, Michelle’s comments show they’re facing the same dating milestones as other young adults, just with a bit more public scrutiny.
The sisters moved to LA for fresh starts and new romances
After years of living under intense scrutiny in Washington D.C., both Obama sisters have relocated to Los Angeles, marking a dramatic shift in their lifestyles and dating options. This move to the West Coast has opened up a whole new world of potential partners – from entertainment industry professionals to the children of Hollywood stars. For young women who spent their formative years surrounded by politics and security details, the relative freedom of life in LA must feel liberating. Their new California lifestyle has clearly expanded their social circles beyond what would have been available to them in D.C. or even during their college years at Harvard and the University of Michigan.
The sisters’ move to Los Angeles seems to have coincided with both of them developing more serious relationships. For Sasha, the transfer to USC led directly to her meeting Clifton Powell Jr., while Malia’s entertainment industry connections in LA appear to have introduced her to figures like Dawit Eklund. Living on the opposite coast from their famous parents has given the Obama daughters space to develop their own identities and relationships away from the political spotlight that defined their childhoods. This physical distance from Washington appears to have allowed them to explore romantic connections that might have raised more eyebrows in political circles, embracing partners from creative industries that align more with their own career interests and personal passions.
From secret service chaperones to dating the children of Hollywood stars, Malia and Sasha Obama’s romantic lives have certainly taken some unexpected turns since their White House days. As they continue building their adult lives in Los Angeles, these former First Daughters have shown they’re determined to chart their own paths – including in their love lives. While they maintain their privacy, it’s clear they’re embracing relationships that reflect their own interests and values rather than their famous political background. Whatever happens next in their dating lives, one thing is certain: these aren’t little girls anymore!
