That was sort of kiboshed, thanks to that reveal about Terry's true origin in JLU. At the end of that episode, he was last seen talking to Dana on the phone, asking her to meet with him to discuss something.
He was holding a wedding ring as the scene went Fade-to-Black.
Did you watch the Behind-the-Scenes segment when they talked about that? Bruce Timm had sent a story idea to the writers about an episode where it was very important that Terry finally make a date with Dana at the end, and Alan Burnett interpreted that as Dana breaks up with Terry for good and Terry finds comfort with Max. It's hard to blame Timm for vetoing something that went so against what he asked for, and the rewritten episode wouldn't have reflected well on either Terry or Max.