Just when you thought Sterling Brown's night couldn't get any worse ... we've now learned the NBA player was on a 1st date with a woman when he was tased in a Walgreens parking lot.
TMZ Sports obtained the file and video from the internal investigation into the Jan. 26 incident -- which made national news for the way Milwaukee PD officers aggressively handled the Bucks player, whose only mistake was parking in a handicap space.
Cops took Brown down to the ground and tased him -- despite the fact video evidence showed he never resisted or seemed to pose a threat.
Now, we've learned the woman who was with Brown that night told cops she barely knew Sterling because they were on their first date.
When cops put the woman into a police cruiser to take her home after Brown was arrested -- cops apologized to her for ending the date ... and joked with her about the evening.
In fact, one of the cops joked about Brown sliding into her DMs.
The unidentified woman laughed at the jokes -- and cops ultimately told her to "give him another chance."
Brown was never charged with a crime -- but he later filed a lawsuit against the PD claiming he was violently mistreated.
As for the woman, no word if he ever saw her again.