1. Prue knew him in high school. They both kept lists. Andy Justin Tom Kevin

2. Piper’s relationship with him was doomed from the start - when she met him, he was already dead. Manny Mark Mac Mike

3. He was Phoebe’s biker buddy who developed an obsession. Otto Helmut Hans Oscar

4. Paige dumped him because of her abandonment issues, then reconsidered his invitation to drive down to Big Sur. Trevor Trey Trent Travis

5. Prue duty-dated him even though he was dull. Derrick Dick Darren Dixon

6. Piper thought he was her dream lover - until she discovered that it was Leo all along. Ryan Ryder Riley Rick

7. Phoebe met him when screening bachelors for a charity auction. Alan Owen Evan Ivan

8. Paige couldn’t relax with him - she kept orbing out at inappropriate moments. Dave Donnie Dan Darryl

9. He wanted a serious relationship with Prue, but she couldn’t condone his ethics. Jordan Jack Jason Jared

10. Piper feared she was pregnant with his evil spawn. Jeremiah Jeric Jeremy Jerome

11. He used his relationship with Phoebe to help him fence stolen property. Clyde Cleavant Clarence Clay

12. When Paige learned that he was married, she orbed him into a jail cell. Nate Necromancer Ned Necron

13. Morris suspected that this guy might be stalking Prue after she stood him up for a date. Shannon Shamus Shane Sean

14. Piper thought he wanted to date her, but he was really looking for an ice-cream truck. Nathan Caleb Seth Amos

15. Phoebe fell for this ex-demon, then discovered that he had only two weeks to live. Donovan Drake Carl Cole

16. He was Paige’s Mr. Wrong - the backfire when she conjured Mr. Right. Vinceres Victor Vincent Van

17. He was the first person Prue used her powers on, although she didn’t realize it at the time. Roy Roger Rolland Robert

18. For 24 hours, he reminded Piper of the importance of love. David Samuel Daniel Samson

19. Phoebe only agreed to a date with him because as an empath, she was channeling his feelings for her. Chad Christopher Charles Christian

20. He was more than Paige's couch buddy. He wasn't evil, but he was “wickedly smart” and “perversely funny.” Kyle Max Glen Richard