Now 6 months after that call originally aired, we now find that Judy surprisingly went to lunch AND a dinner with Simon. After two dates they both decided a relationship between the both of them wasn't going anywhere, and they decided not see each other any longer. Simon respectfully moved on and didn't become the "creepy guy" like we all thought he would be.
Simon ended up moving out of the apartment complex and moving to New Rochelle, the next town over. Judy tells us she tried, and gave him a shot but younger guys just are not her thing.