& Anna :) ♥

I never liked Dean with Jo or Anna. And him and Cassie where okay but not my fav. I actually really liked Jamie. She was sweet. I liked Layla too. My fav girl friends for the boys are usually one episode wonders :)

I picked Cassie, but Jo's right up there. I really liked Andrea too though...

I just hope Dean finds someone to settle down with after this whole beating Satan thing (But not Anna....didn't like her...)

i like her. the rest, nah. i hope he finds the right person when the show wraps up. not any of the above though. deff not anna.

I really liked Anna. She was there for Dean and he was more vulnerable with her than he ever has been around a girl. And i really love her as character 2.

honestly i thought they were sooo cute :) lisa + dean + ben = cutest family <33 aww. i really wanted him to be his son :'(

hate all . just like her

^^ What she said. I was so hoping that Ben would be Dean's son. I liked Cassie and Anna. I know that Jo was originally intended to be a love interest for Dean, but I think they had more brother/sister chemistry than anything else.

and I like Lisa.. Brunettes suit Dean more :)) no offense non-brunettes :)))))

oh come on jo is the annoyest girl in this show.i think Anna or Lisa is cool for him:)

Honestly, I don't know... But I think I chose Anna because she's the newest and she just had something that seemed good for Dean, (and I'm not just talking good because she's an angel!:)

But actually i love them all, but Jo is my fav and then Anna, Carmen, Layla and Lisa. Cassie is my least fav...

Because he really loved her, the others were just flings :)

honestly i don't like Jo...so i think Anna could be the best for him,i like the connection they have,but i also like Carmen Lisa and Cassie...and i Agree with Natalie88 brunettes seems to suits him more

I liked Layla, she was sweet, gentle, homely, nice, and in her strong, in her own way. She was soothing.

Huge Joe and Dean fan!

Jo and also Kelly.Season 2,episode 17-Heart.

I thought Carmen was really suited for Dean, and I loved them together! My second choice would be Lisa, then Cassie. I couldn't stand Jo - I agree with acklesgirl87 that they seemed more like brother and sister. There was no spark and no chemistry in that relationship. I also don't like Anna, for the same reasons.

Jo <3 and then Anna ! :)

In Supernatural when he is Dean I pick JO, be cause JENSEN is mine...

^^ No he's mine...can't you tell by my user name? LoL

Jo ; Anna & Lisa.

God I HATED Cassie. Lol. But this was so hard because I love so many of the others! Way opposite of Sam's love interests. I loved Jo the best, for sure. But I also liked Anna and Bella. :)

I don't even remember who Carmen was. I know Jamie was only on for one episode, but she was great. She would have suited Dean.

i hate cassie.....and i did like dean and jo together but lisa and dean won out for me

i would like to see dean and anna get together again in season 5 because they look like a good couple

I loved Dean with Anna, they were great together...but i liked him and Jo to...Pretty hard chioce

At first I was interested in a Dean/Jo relationship, but then it became clear to me that they were much better off friends, in their, like others have pointed out, brother and sister way.
I also like Layla and Jamie, but Anna is by far my favorite. I loved her with Dean :)

Why is Bella not an option? lol

i love dean and jo cuz all th others were just flings. dean met jo in season 2 and when she came back in season 5 he still liked her and treated her different from every one else in a more respectful way. dean was probably taking it slow with jo cuz he wanted it to work out and not be over with the next morning :) x

i just like her !!
and started to like jo when she died !:D

and I also liked Lisa

I wish Dean would have given her a chance... she understood the job and never tried to kill his mom to end the family line like Anna did. She said Sam had to die but she goes back to when his mom was pregnant with him so she obviously didn't care if he died too... so any of them except for Anna.

I liked Lisa with Dean but it was sad he had their memory wiped

I loved her with Dean! AU pairing :D

I just really liked her.

@twilighter4evr - it was John Anna tried to kill, not Mary. She deliberately timed it so as to try to prevent Sam from being born while still preserving Dean's existence.

Like a lot of earlier posters here, I see Dean's relationship with Jo more like siblings (and I ship her with Sam instead). I felt like he only chose Lisa because she had a son/because that was a way of having a new family. I liked him with Anna originally, but after S5 I have to hate her. The others are one-episode-love-interests, but he and Cassie had more of a history.