>>91354992Babs is a mess because she was basically a cheap fling and by the time either her OR Dick got actual serious characterization, Dick hadn't worked for Batman for two years and Babs was actually ENGAGED, and not to a member of the Bat-family either. Her sudden enduring love for Dick was something touched upon first by Chuck Dixon (though it needs to be said that Dick banged Huntress far more often and Dixon teased him with EVERY woman he ran across), but Simone made it a far more significant part of both of their lives because, let's face it, she self-inserted onto Barbra Gordon and thus liked Robin as a kid too. This messy shit along with Bab's own personal continuity issues and changes mean it never sticks and almost the moment it gets "serious" it ends just as fast between them.
Kory dumped him after their wedding got crashed by Raven going Trigon (for the second time), but also because Batman writers at the time hated that he couldn't use Nightwing in Batman stories as Wolfman had full control over all the NTT characters.
The one romance with legit long-term buildup, emotional connection, and genuine chemistry was him and Kory, but basically when Wolfman was going to tie the knot editorial interference screwed the whole thing into the ground, leaving Dick in a state of perpetual relationship limbo where he gets passed around a LOT.