Richard made his first appearance in "The One Where Ross and Rachel... You Know." Although the episode revolved around Ross (Schwimmer) and Rachel (Aniston) as they consummated their new relationship, Monica had her own romantic revelations when she catered a gig her mom (Christina Pickles) had landed her. That gig was hosted by one Dr. Richard Burke, a newly divorced man who also happened to be best friends with Monica's dad (Elliott Gould).
Because of that connection Richard and his ex, Barbara, had been the Gellers family friends for decades. They had also known Monica and her brother, Ross, ever since they were children, and had watched them grow up over the years. Further complicating any potential trysts between Richard and Monica was the fact that Monica went to school with Richard's daughter, Michelle. Add in a son, a couple of grandkids, and a 21-year age difference, and this May-December romance definitely got off to a rather awkward start.