Hmm. I think they were deffinately an intended couple on “Woody’s Roundup” , however, Jessie and Woody act differently than there characters on the show and they deffinately have a brother/sister relationship. To me Woody seams like Jessie’s older brother…someone to look up to and for Woody , Jessie is someone he wants to protect. I’ve been reading a lot of fanfictions lately where the characters on humanized, and in every one I’ve seen Woody and Jessie are siblings…so…hhaha.But then again who knows?