8 TV Love Triangles That Worked (And 3 That Didn't)

4. Dean, Rory & Jess - Gilmore Girls

The Rory/Dean/Jess storyline caused a stir during Gilmore Girls' initial run, and it became such a thing that people still debate on which of the guys Rory should be with to this day. Much like the earlier Roswell entry on this list, what made this love triangle stand out was the fact that Rory's two potential suitors couldn't have been more different from one another.

While both Jess and Dean were insanely attractive, Dean was the good-hearted guy that every resident of Stars Hollow adored, while Jess was the one-syllable-uttering bad boy, who rebelled against every adult in town.

Rory couldn't have found a more perfect first boyfriend in Dean, but as she continued to grow, she was experiencing other feelings, and found herself drawn to the resident bad boy. Again, the conflict here was excellently depicted, and we still feel sorry for Rory for having to make such a choice.