In Superman/Batman, right? Did they ever do anything? Been a while since I read that one. I just remember him holding her but I don't recall if they ever did anything further because I think he was just overwhelmed by her beauty or something. He did something similar in Trinity (by Wagner) where he basically forced himself on Diana.
AFAIK, she only slept with Ted Knight. I can't recall an story that paired her with Grant even if the two were friends.
Kory's always been okay with their relationship being open, it was Dick who wanted to be the monogamist in the Wolfman/Perez stories. I can see Dick being tempted to follow up by hooking up with Barbara but now it's her whose the monogamist.
Nothing came out of it. Pardon the pun. Bekka had this power where any man who has great angst would fall helplessly attracted to her and vice versa. The whole story was about Bruce trying to keep his giant Bat-boner down while he searched for a missing Superman in space. It was hilarious. XD Especially with them ending up in so many situations where they had to be close physical proximity. They came close to doing it but then plot stuff kicked in and they had to go deal with that, then at the very end of the story it looked like they were finally about to consummate when Orion showed up and whisked her away.
Funnily enough, it was written by Alan Burnett who was the story editor/writer/producer behind Superfriends, Batman: Mask of the Phantasm, B:TAS, S:TAS and Static Shock. The art was by Dustin Nguyen, I think this may have been before he worked with Paul Dini on 'Tec and Streets of Gotham' and in very mid-00', style, the art made it very clear that Bekka didn't wear underwear under her costume.
I know. I'm just trying to explain away incongruity between Dick hitting on Babs in Nightwing: YO while still being a serial monogamist in NTT. Maybe he didn't want it but was tempted because of Barbara then of course he went back to Kory and then everything played out as it did in the books.
Sounds like she is telling him to find other women and even Bruce looks uncomfortable with whatever went down between him and Barbara.
Prior to that terrible Batman Beyond comic with the miscarriage aside, I always figured that the two had a fling, regretted it and never spoke about it again.