No, Usher and Aaliyah were not romantically involved or "with" each other in a dating capacity. Their relationship was primarily one of friendship.
The Nature of Their Relationship
Usher himself has clarified the dynamics of his connection with the late R&B star. He stated that while they were good friends, their relationship never progressed to a romantic level. Usher indicated that he would have dated Aaliyah and that they had even talked about the possibility, but it simply "didn't get around to it" and they "didn't do it."
This suggests that although there might have been a mutual interest or contemplation of a romantic relationship, it remained unfulfilled, and they maintained a close platonic bond.
