Omid never met Meghan (except afterwards), all his contact with her was via Jason Knauf, who likely would have vetoed or steered her away from anything that made the Palace look bad.
Actually, the only contact that we know about for sure is via Jason Knauf, who was present at the very start of their relationship, and acted as a go-between (we know this from his emails from the time he was working for the Sussexes). He stopped working for the Sussexes late in 2018 however.
It is quite clear, however, that the relationship between the Sussexes and Omid continued after Knauf’s departure (Omid had the exclusive about their intentions around titling Archie after his birth, for example, and the judge in Meghan’s case against ANL made it clear how close Omid was to her team - being sent copies of court filings to tweet out immediately after they were filed). So personally think it’s very likely that the relationship developed and deepened considerably after Jason Knauf left the Sussexes employment.