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Web in december 1999, puff daddy and j.lo jennifer lopez were arrested in new york city after a shooting in a nearby. Web jennifer lopez and diddy, then known as puff daddy, dated for almost two years and were both arrested after the. Web combs and lopez were arrested after fleeing the scene with a gun in the trunk of their lincoln navigator. Searched told series of sexual misconduct lawsuits settled. One of the victims of the 1999 shooting, involving. In december 1999, puff daddy and j.lo jennifer lopez were. Diddy has had many legal incidents, including a famous arrest with j.lo. Diddy arrested along with jennifer lopez.