I really did not get the feel that Jimmy was on the boyfriend track. Very attractive, and so tall, but he's too busy being inegmanic and tall... Did I mention how tall he is? The Winn character is way too far into the friends zone to get a date with Kara, but that just makes him Ducky. Desperately in love and ignored. It also might make Winn become a super villain to get her attention? Winn Schott, the name they are using for this kid, is taken form the Superman Villain "The Toyman", so we have that to deal with at some point down the line.
I don't see "James" being a love interest...more of a mentor figure, odd as that may seem. (You've come a long way, Jimmy.)
Except and they might cut this in the final thing - Kara has a scene with Winn where
He says something like "you know when love hits because it's like KAPOW!" and she meets James, leaves the room and said "KAPOW!" - so that scene is a a bit pointless if he's not intended to be the love interest. However the guy playing James is a bit bland so who knows...