Bruce Wayne, despite the spying that he partook in to gather the weaknesses of his friends and enemies alike, really didn’t care all that much about other peoples’ personal lives. Obviously, he took note of some major things; marital status, employment, residence, and holidays were all things that he kept track of and tried to follow. It helped him in his vigilantism, of course, but it also helped him with his posturing as a playboy. If he couldn’t keep up with the current gossip then he’d never be able to fool them.
But generally, he took a “don’t ask, don’t tell” approach to those kinds of things.
This approach ended up coming back to bite him in a big way, however, when his fifteen-year-old ward Dick Grayson approached him tearfully and came out as bisexual. He was more than a little bit shocked, and Dick had taken his initial unresponsiveness as a rejection. It took several hours of consoling to convince the boy that no, he wasn’t angry or upset, and yes, he was perfectly willing to hear him out about his woes with the boy he’d been seeing in secret.
Bruce tried to keep a slightly better eye on Dick’s relationships after that, when it was revealed that Roy Harper had been stringing along both Donna Troy and Dick, and that it had culminated in a tension that somehow rivaled that of Roy’s and Wallace’s (again, something that Bruce hadn’t actually noticed, but apparently had been weighing heavily on Dick’s conscience).
Ultimately he never ended up being Dick’s go-to emotional support. But he did receive the occasional update on Dick’s relationships from then-on out, regardless of who he was seeing.
It was much less of a drama when Jason came out to him. He simply mentioned that he was seeing someone one night on the way back from patrol.
Already used to being on the streets, Bruce supposed it wouldn’t have made much of a difference to Jason, whether he’d been kicked out or not. And it wasn’t as if he was talking to Dick, to be reassured that Bruce had no issue with it. But he did make sure to squeeze Jason’s shoulder as they went up to bed, and to remind him that he was always welcome at the Manor, regardless.
He did have to stop and talk to Oliver Queen the next time they encountered each other, though. After what had happened the last time one of his boys dated Roy Harper, he wanted to make sure that Oliver was actually aware of the situation this time and could do something about it from that end.
It was Tim who really surprised him with his coming out. Not because of his sexuality, but because Bruce couldn’t imagine what on earth drew his quiet, intelligent ward to a brash, rambunctious young man. Not to mention the fact that he was dating the son of his father’s murderer. He’d expected Tim to be dating Bart Allen, or Connor Kent – hell, even Conner Hawke. But Owen Mercer? That actually threw him.
The conversation with Tim wasn’t so easy as it had been with Jason or Dick. He had to toe a very fine line between reassuring Tim that it wasn’t because he was bisexual that he was angry. It was his choice of partner.
In the end, he obviously wasn’t able to toe that line very well, because Tim stormed out of the manner crying. He made sure to give Dick a call and warn him that there would likely be a crying Robin on his doorstep, and somehow ended up being berated, because “Honestly, Bruce. I’ve seen them together and they’re wonderful for each-other. Why did you have to go and do that?”
He’d somehow missed the memo that Dick had been leading a team with Owen on it for a while. Either way, he was thankful that Dick and Tim had each-other to rely on when Bruce’s emotional stuntedness got in the way of his being a reliable guardian.
By the time it got to Damian, Bruce was basically prepared for anything. Sleeping with an alien? Been through that with Dick. Boyfriend caught up in a drug-bust? Dick and Jason. Dating a supervillain? Both Jason and Tim had done that, and somehow both managed to make it work.
So when Damian sat him down before patrol one night, Bruce was fully ready to give the “I don’t care that you’re dating a man, just be careful” speech. But he had to change it up on the fly when Damian said that he was bisexual, but was dating a girl, and had been for several months at that point.
Apparently he’d just wanted to be up-front with Bruce about it, to avoid any awkward conversations in the future should he and his girlfriend break up, and should he begin dating a man. Dick had encouraged him with this, and so, apparently, had his girlfriend’s brother.
“And one more thing,” Damian had added, when they headed down to the Batmobile together, “is it alright if she joins us on patrol sometimes?”
Of course, that brought up the long conversation about who could know his secret identity (thankfully it was quickly cleared up that she had always known), and then the repeated “You may not bring meta heroes in to Gotham for routine patrols, Damian. It is unsafe and unnecessary”.
Eventually, Bruce had to sit all of his boys down for a talk. Word had started to get around the superhero community about who he was dating. He knew Dick had already heard, and he was certain Tim would have heard by now, but Jason still wasn’t properly involved with superheroes again, and Damian tended to avoid participating in gossip as if his life depended on it.
Dick was smirking at him when he sat down on the sofa, wrapping an arm around Damian’s shoulder while maintaining painfully strong eye contact with Bruce.
“So,” He said around his smirk. “You have something you wanted to tell us?”
“Of course he does, he –” Damian started pushing Dick off him, and Dick turned his amused smile to his “brother”.
“I know, Damian – I’m just teasing him,” He interrupted, and turned his gaze back to Bruce.
“So what is it? Now that we’re all finally here,” Jason glared at Dick, who reached out to poke him with his toes.
Bruce took a deep breath in, and waited for the boys to settle, before making eye contact with all of them (and lord, was that uncomfortable). “So, as some of you have heard,” He paused to let Dick snort, “I’m seeing someone right now.”
Damian’s ears immediately perked up, and he scowled. “It’s not –”
“It’s not your mother, no. And it’s not Selina this time, either.” That caught Jason’s interest. Tim had started texting someone, but had a knowing smile on his face. “I’m seeing Clark,”
There was a long, awkward pause, before -
“You’re seeing who –”
Bruce closed his eyes and tried to tune out Jason and Damian’s yelling, while Dick cackled in the background. No matter what, he was glad to have his boys here for this. He almost felt like he owed them the conversation at this point.
“it’s okay, Bruce,” He opened his eyes to see Dick reaching over to pat his hair. “We love you no matter who you’re fucking.”
And that caused its own chorus of screaming, with Damian eventually leaving the room with his hands over his ears because “I don’t need to hear about Father’s sex life,” and Jason admitting to him quietly that “Bruce, I do actually have a sex thing I need to admit to you. You’re going to hate me for it –”