In 1995, after Aaliyah and R Kelly's locked tight marriage was annulled by her parents, they did actually date. But they dated for only 3 months before they split. She kept this part of her career secret, because she was still getting heavy rap for being married to R Kelly the year before when she was only 15.
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Aaliyah and Ginuwine dated for a year (1997 - 1998). Ginuwine has written songs about Aaliyah, though never vocally mentioning her name, magazine articles with interviews from people close to both Aaliyah and Ginuwine said that even after they ended their relationship, he still carried very strong feelings for her. "Differences" was also written speaking about his relationship with the late singer. RIP Aaliyah.
Aaliyah always denied dating Jay Z, and I am a big fan of Aaliyah and just from my perspective I always sensed this "chemistry" between the both of them. Especially during the time of Aaliyah's death Damon took it extremely hard because that was his fiancee he just lost. But more than anything Jay Z took it pretty hard too, he dedicated several concert tours to her and there is also a song he wrote a while ago.. like back in 1999 or early 2000 that was inspired by her.
Even though her and Jay both denied being a couple, there was definitely something there. Maybe not a relationship, but maybe a crush.
Aaliyah and Jay-Z were NOT romantically involved with each other. If you go to YouTube and type in Aaliyah: MTV Stripped I believe on part 1 or 2 she talks about the situation. Her and Jay were always good friends and nothing more. And there were even people close to her, after she passed who said Jay always liked Aaliyah but she only wanted to remain friends with him. After people seen pictures of them together that's when they automatically assumed that Aaliyah and Jay-Z were together. But Aaliyah was part of the Breakfast Club which consisted of Jay-Z, herself, Damon Dash her soon to be fiancee and a few other people including Missy Elliot. They always hung out with one another and went to parties together. But the media blew the whole situation up, making it what it really wasn't.
Let this rumor die out of respect for Aaliyah.