Dame Dash has had many ups and downs as an industry mogul, but beyond any music biz frustrations and betrayals--his hardest moment was a personal one. Late R&B star Aaliyah was Dame Dash's girlfriend when she died at age 22 after a fatal plane crash in the Bahamas following a video shoot in 2001. It will be 15 years this August, and Dash talked about that fateful day during a recent appearance on The Real.

When co-host Jeannie Mai asked Dash if there was a possibility that he could have been on that plane back in 2001, he explained that he would've been able to prevent Aaliyah from taking that ill-fated flight had he been there with her.

"There is no chance that, if I was there, we would have been on that plane," he said. "So it would have never happened that way."

He went to say that he didn't want her to go to the Bahamas at all, and Aaliyah herself had reservations about the tiny plane.

"She told me she was going to the Bahamas, and I was against it, like, 'Yo, don't go.' And then down to the last — we had the Blackberry — down to the last Blackberry that we had, before she went there, she was like, 'Yo, I don't like that plane,’” he recalled. “And I was like, 'Don't get on it.' And she was just like, 'You know, I gotta do it.' You know, it was a complicated situation, but she had to go do that video."

Check out Dame Dash discussing Aaliyah's tragic death on The Real in the video below.