Not a big Dean/Jo shipper, but their story was sad

If the question was most heartbreaking death my answer would definitely be Jo, but in terms of romance - the Sam & Madison story tore at my heart the most, especially Sam's face just before he killed her. Broke my heart. :'(

So true

I thought this ending was sad !

Sam and Madison were the most heartbreaking romance because it ended with him being force to kill her

I cry almost every time. This is pure hearbreak! <3

or Sam & Jess I really don't think Sam will ever truly get past the loss of her very much like John & Mary. Sam & Madison are also on my list.

Jo had a heartbreaking death, but the only romance she shared with Dean was a kiss. While Jess was the love of Sam's life, and her death was hunting him for years. :'(

Well, Dean and Jo wasn't really a romance, that was just a kiss. While I always thought that Bobby and Ellen was made for each other, I loved their story line, I loved their AU romance, that was so sad that it wasn't real.

Sam & Jessica - well, that was the romance.

Dean and Lisa - their story wasn't that sad, for Dean ending was sad, but n reallity ut was not really a good romance. I am their shipper a bit.

Mary & John - I call it the most beautiful and the only true romance in this show, yeah there was a lot of heartbreaking moments, but they loved each other so much.

Sam & Madison - it wasn't that big romance, yeah he slept with her, yeah but there wasn't love in this one. It was sad.

But well, I think the most heartbreking romance/friendship is Dean and Castiel , it's not in this list and many of you will protect me, but that what shara Castiel and Dean is the most heartbreaking story ever. Yeah, you may think that it's not the romance, but for me they allways be canon and romance.

Mary and John. John would have done anything to avenge his wife's death.

There was no Dean/Jo romance... But anyway, I feel bad for Amelia. Losing Jimmy like she did would have been hard.

Or Mary and John.

How are Dean/Jo winning this when they weren't even a fully canon couple?!