I find it gross, too, and it's my biggest problem with Batman Beyond, which is otherwise a really great show. It's also weird that this "affair" is never really alluded to or implied outside of that Batman Beyond episode. Outside of that episode, Barbara is just shown having an unrequited crush on Batman, which is nowhere near as disturbing.

"Evil beware . . . we have waffles."

• Raven, "Teen Titans"

the thing to remember though is where in the chronology the relationship Occurs
lets assume the present day series are set in the years they aired +/-; with the Flashbacks in Phantasm that means the DCAU runs from 1991 - 2006
then we time skip to 2055ish for Beyond/Zeta and further jump to 2070 for the Terry/Waller framing scenes in Epilogue.
Joker last appeared in the 'present' as late as 2003 the Problem comes from Tim being low Teens in the 'Return of the Joker' Flashbacks when he should have been pushing 20 at which time since we see no signs of it in the main timeline we can assume Bruce & Barb had not yet 'gone there' at that point
if we put RotJ's flashback in 04, and assume they bonded over grief for Tim's fate
now, Tim's age not withstanding we have to assume Barbara would be almost 25 herself by 2005 so if the relationship only crossed the line post JLU; where exactly is the creepy in a 35 year old Bruce hooking up with a 25 year old Barbara
I could be wrong, but the Dick/Barbara relationship did not extend into his tenure as Nightwing that means they parted circa 1995 which means it was 10-15 years between those relationships

The main reason why Bruce "possibly" hooked up with Barbara?
Paul Dini
Seriously, check the guy out. He's a big ol' perv and he has little problem with showing it. The man has talent, sure, but his proclivities are clear and obvious.
I'm glad that their "relationship" never took place on the show, so I can easily ignore it.

To me it isn't very surprising. Think about it, Barbara is one of two, maybe three or four women in the world who truly knows him and what he is all about. One is Leslie Thompkins, and I don't cougars are Bruce's kind of catwomenthe other two are Talia al Ghul and Andrea Beaumont, both of whom fall on the opposite side of the law to Bruce. It stands well within reason that romantic feelings would develop between the two, perhaps spontaneously during some discussion of Bruce's tragic past and Barbara trying to comfort him. Is it on the up-and-up morally? Perhaps not. But, Adam West's incarnation aside, I've never seen an adaptation of Batman where he is supposed to be completely free of flaws.

It just doesn't sit right with me.

The age gap thing wasn't an issue much, maybe cause I've known people who had relationships with age gaps like that.
But the fact that Barbara dated Dick and is Gordon's daughter does make it kinda creepy.
Although I can see how it might happen. They were workign together and both have the same 'burden', the secret identity so they are the only ones who really 'know' each other. I mean Barbara can't really tell anyone she dates that she's Batgirl and same with Bruce, so looking at it that way, it is very possible that they could become close. So I don't mind it much.
Diana is a remarkable woman, she's a valued friend. She's standing behind me, isn't she?

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I'm confused that people would be shocked by this. Bruce Wayne is a huge womanizer in BTAS/TNBA. It's implied that he's slept with Talya and Selina Kyles, and there's a ton of sexual tension between him and Poison Ivy, and between him and Harley Quinn. Not to mention that Christmas episode in TNBA in which Harley Quinn and Poison Ivy turn him into a boy toy with mind control toxins.

And you wonder why Dick doesn't like the old man

The age difference is kinda staggering as well. Bruce, in the series, is depicted as being in his thirties (as he has been Batman for around ten years, at least at the time of the 'Phantasm' movie). Dick is around 19-20 and Barbara is probably around the same age, give or take a couple of years. So basically Bruce slept with a girl who is a good ten years his junior at the VERY LEAST, is the daughter of one of his oldest friends AND the ex-girlfriend of his foster son.

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That's it, you're going on the ignore user list.

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But why? Why do it just to annoy the fans?

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I can only imagine how Batman's pals in the Justice League would react to that.

Oh yeah, I caught that episode of Batman Beyond, that scene didn't sit well with me either.