1. HOLLY MADISON Madison was Hugh's main squeeze for years, which led Holly to think that he was going to marry her and, in turn, start a family. However, he was afraid to commit. When Hefner tweeted that he'd be screening Runaway Bride instead of marrying Crystal Harris, Madison tweeted in reply, "Wish I was there to support..." We do, too, because we love happy endings. Both literally and figuratively.