Brad Womack & Emily Maynard
When Brad Womack proposed to single mother Emily Maynard, we had major heartswell. These two looked like they had the kind of lasting connection that could weather the post-Bachelor media blitz. Alas, these two — who became engaged in March 2011 — didn’t make it through the summer. After a lot of speculation over the cause of their split — the distance? her 5-year-old daughter Ricki? — Brad finally fessed up and took the blame, telling People, “The demise of our relationship was completely my fault." While Brad licks his self-inflicted wounds in Austin, Emily gives love-on-TV another shot as The Bachelorette.