It’s no secret many celebrities wanted to date Aaliyah back in the day. Aaliyah was a beloved R&B star taken from the world too soon. Known for her trendsetting fashion, captivating dancing, genre-defining music, and beauty, many men longed to be in her presence. While on this planet, the singer did date some high-profile guys, while others confessed to wishing they had a chance to date her or missing out on their moment. Let’s take a look at the men in Aaliyah’s life.
Aaliyah kicked off her career in the early ’90s during a boom in young R&B talent. She quickly became a fixture in teen magazines and television programming. Another young artist making his way at the time was Usher. Both celebrities went on to be juggernauts in their respective lanes, and for a moment, they were also really close friends, according to the “Nice & Slow” singer. Usher recently confessed that he and Aaliyah used to hang out a lot and watch movies. While he knew he liked her, he says he never made a move to date the singer, and they eventually grew apart. He says he regrets never pursuing her.
Aaliyah would go on to date another really close friend of hers, however, according to an unauthorized book about her life. In Baby Girl: Better Know as Aaliyah, the author details a secret relationship between Aaliyah and co-writer Static Major. The two celebrities became fast friends after being connected through Timbaland and Missy Elliot. Static would write Aaliyah’s signature hits, “Are You That Somebody.” According to Static’s mother, the pair dated for a while, and Aaliyah came to the house a few times. Reportedly, “Are You That Somebody” was written about their romance. Static would go on to pen several other Aaliyah standards, including “Try Again,” More Than a Woman,” and “Rock The Boat.” Unfortunately, Static would pass a few years after Aaliyah, so the two celebrities never got to discuss their chemistry or how it was to date privately.
Timbaland was around for Static and Aaliyah’s time together, and while he’s never confirmed or denied it, he did make a shocking confession about his own feelings for Aaliyah. Timbaland was a few years older than Aaliyah and saw her as a sister, but copped to secretly having feelings for her. While he never acted on it, he says his love for her was so strong he would eventually go on to marry a woman that looked very much like Aaliyah.
Around this time, Aaliyah got cozy with another ’90s icon, Ghostface Killa. In his biographer, WuTang member Raekwon recalls how much the group loved Aaliyah and her music. At one point, Ghostface told the guys he was talking to her, and nobody believed him. To prove everyone wrong, he pulled up to Raekwon’s home studio in Hollywood with the singer. Rae says he did not know the two were there and walked in on the pair napping on a chair together. He described their relationship as “puppy love” and says they had a lot of love for one another despite not going public with their romance.
Dame Dash and Jay-Z were also two celebrities coming up in the ’90s while Aaliyah was. They founded Roc-A-Fella records together, and Jay was on his way to becoming the superstar and mogul we all know and love. While his name is now synonymous with his wife, Beyonce Knowles-Carter, at one point, he had his eyes set on a different R&B Diva. Rumors of Jay-Z trying to court Aaliyah date back years. However, it would be his friend Dame that would go on and win her heart.
Dame Dash and Aaliyah were dating for the last year of her life and reportedly very in love. It was Aaliyah’s only public romantic relationship during her lifetime. It was rumored that she was actually rushing home to surprise Dame from her “Rock The Boat” shoot. Unfortunately, she never made it home. Dash has spoken candidly over the years about his feelings towards Aaliyah and how much the loss has affected him. While he did eventually move on and get married, his wife said that Aaliyah is a constant in their relationship and that she often prays to the late singer for guidance and knows that she still watches over and loves Dame.
DMX and Aaliyah shared a beautiful bond as well. The two celebrities got close while filming Romeo Must Die, and he was genuinely heartbroken when she passed. They had undeniable chemistry during the shooting of their video for “Come Back In One Piece.” DMX girl at the time says she was not too happy about how much attention he paid his collaborator and how smitten he seemed by her.
Since her passing other celebrities like, J Cole, Chris Brown, Ty Dolla Sign and Drake have sung her praises and confessed their desire to date Aaliyah. Drake even tatted Aaliyah on his body, while several other artists make mention of her in songs and interviews. J. Cole recalled being so distraught but the death of his childhood crush that he made her a beat as a tribute. Who are you most surprised Aaliyah was connected to? Which celebrities would you have liked to see her date?