the first is his college ex that is now haunting his list since accepting a job as the morning show host at the news station his step-dad works at, the next is someone he met while he was at bu for grad school six years ago, dated a few weeks, school got busy and they dropped it. they rekindled for a bit post graduation until he ghosted and surprise, he finds out they're the board president's kid for the nonprofit he works at. last is the age inappropriate girl (thinking 25 max at the time) who was using him as a come up and ultimately hit the jackpot when she ghosted and reappeard six months later sporting a giant rock and the title of future stepmom number five. that's right, she got engaged to his dad.