Holly Sweeney is Rory’s high school sweetheart. They dated for a really long time and still remain friends to this day. They are such good friends that Holly follows Rory on twitter. Holly is now married to a hockey player and they have a child named Max. When Rory learned that Holly had a baby Rory visited Holly and gifted her son Max a pair of his first Nike football shoes.
This one didn’t end so well…. Caroline is a world class tennis player that dated Rory following his breakup with Holly, his high school sweetheart. Rory and Caroline got so serious that they got engaged. When Rory got engaged to Caroline his golf game suffered. He was no longer that threat on the course that he once was.
Rory had a really nasty break up with Caroline… Caroline was so upset with how the breakup went down that she went to the media and told them how it happened. Caroline said that Rory broke off the engagement during a 10 minute phone conversation. She was so mad that Rory didn’t do it in person. She said that it was her last phone call with Rory and since that call she hasn’t heard from Rory. Shortly after the breakup Rory’s golf game improved drastically..
Erica Stoll is an employee of the PGA. She is a low key person and possibly just what Rory needs in a future spouse. You may think that Paris has lost some of its luster, but Rory certainly doesn’t think so. In 2015 Rory and Erica were vacationing in Paris when Rory decided to pop the question. They have been engaged ever since and both seem very happy.