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As far as Tim was aware Bruce had never been outwardly aggressive or negative about queer people. He never seemed to have a problem with his cousin being lesbian, and he was generally more upset with Harley and Ivy's criminal antics than with them being together. Diana was another openly queer person they knew, and Bruce was close friends with her. Why does Bruce know so many queer women? The only queer man Tim could think of was Ghost-Maker, but once again he falls under the category of "Bruce has bigger issues with him".
No matter who he managed to think of it didn't feel comparable to him coming out. He was Bruce's son, people tended to feel differently the closer their relation is. Tim never had the chance to come out to his dad, as in Jack Drake, but he'd certainly imagined it many times. Jack was the type of person to be amiable in public, but then he'd mutter and grunt complaints about eccentrics on the drive home. If Tim had the chance to come out he most definitely would have been met with a negative reaction. Not that it will ever matter, but he also believes Jack would've come around eventually. He knew his dad had loved him. He would have just needed time.
None of that was important though because Jack Drake was dead, and the father who he did have was Bruce Wayne. Bruce who was almost entirely different to Jack. Accept for the fact that he was no amateur to putting up false fronts. If he came out to Bruce only to be met with disappointment or unease it'd be crushing. Also, although he thought it unlikely, if he were to be met with straight rejection he'd need to be prepared. In any other circumstance Tim would say he could anticipate and understand Bruce's thinking better than most. In this subject he was lost though. He constantly felt like he was only seeing what he wanted to see.
Therefore, he had to get a second opinion. His first thought of course was to go to one of his siblings (probably Dick) or Alfred. They knew Bruce well, his good and bad qualities, their assessments were likely to be accurate. However coming out to them just as a step for coming out to Bruce felt cheap. They deserved their own moment. He considered just asking his friends for advice, but the Young Justice members didn't really know Bruce well enough to gauge his reaction.
It had to be someone who knew him both as Bruce and Batman, and they couldn't have such a heavy bias that they'll lie in favor of a positive response. Perhaps someone in the Justice League. Of course many members were off limits just based on the fact that Tim didn't know where their opinions stood either. The people Bruce was closest to that were also known to be supportive were probably Clark and Diana. Clark was too positive though; he'd never think of his close friend being hateful in some way. Diana was too separated from average society. She grew up on an island of only women, queerness isn't going to be something she entirely understands the weight of outside of Themyscira.
Tim had almost considered having to change his train of thought to which rogue would probably provide the best advice when it hit him. The most obvious answer.
—
Oliver didn't know the third Robin that well. In the vigilante life they surprisingly didn't have many reasons to cross paths. He supposed Cissie was on the same team as Robin, but him and Cissie weren't quite close enough for her to tell Oliver much about him. Outside of vigilantism he'd only ever seen Tim Drake at the occasional gala. There the boy is likely to be seen wall flowering or dealing with Brucie antics.
All this to say it was a surprise when at one of these events Tim asked Oliver if he could speak to him privately. At first he was afraid that something horrible was about to happen and the young vigilante needed to alert him, but then that didn't make sense because why wouldn't Bruce speak to him. Surely Bruce speaking with an old friend privately is more inconspicuous than his son doing so. Bruce seemed to just be doing the usual performance engaging flirtatiously with people at the gala. What could this be about?
Once they found a room that Tim deemed suitably private he said, "I'm debating on whether to tell Bruce something. I need you to give me your honest opinion on how you think he'll react." Why the boy had deemed Oliver to be the best person for this was beyond him. Yeah, him and Bruce were long time friends, but they were also long time annoyances towards each other. There's certainly people Tim could find that probably knew him better than Oliver. Bruce would never raise a fool though, so he trusted whatever Tim's reasoning may be.
"Is it something regarding your guys' line of work?" If this had something to do with hero work then the issue could range anywhere from he wanted to change his costume to he killed someone on accident.
"No, its..." Tim took a breath as he hesitated, "I'm bisexual. I'm not sure how well Bruce will take that. If it's going to create distance or strife between us then I don't want to tell him. At least not until I'm prepared to live independently of him." The kid seemed so nervous picking at his fingers and looking at the spot right beside Oliver's head instead of actually at him.
Unfortunately Oliver was mostly just trying not to laugh. The concept of Bruce Wayne being homophobic was absurd to him. Had he truly never told his kids? Not to mention that according to Bruce's bragging Tim was one of the best detectives in the world. He supposed the easiest way to end this conversation was to just say, "well you can't be worse at being bisexual than Bruce considering at least one of his ex boyfriends went insane and murderous." That would be wrong though. It should remain Bruce's choice whether he told his kids about his sexuality. Plus Bruce wouldn't appreciate Oliver airing out any embarrassing secrets, and Oliver can only be on Bruce's bad side so much.
Instead Oliver needed to find a different route of reassuring the kid. "You have nothing to worry about Tim. Bruce wouldn't be upset with you about your sexuality. If he was then he'd be an idiot. Do you think he's an idiot?"
"No, of course not."
"Then there you have it. I fully believe everything will be fine, and if things go wrong then I'm sure Star City would be happy to have someone with your skill set."
Tim scrunched his nose in distaste, "if things go wrong I think I'll still stick around in Gotham, or go to Bludhaven if I really have to."
"What's wrong with Star City?" Oliver mocked offense. He'd never understand why people from Gotham felt such a deep loyalty to the worst city. They walked back to the gala as Tim explained his reasoning for loving the wretched city so much.
—
After gaining Oliver's assurances Tim was more confident about telling Bruce. He still needed to find the right moment though. The obvious route would be to just sit him down sometime and tell him. Building up the moment that much would be nerve wracking though. Knowing himself, Tim would chicken out and end up saying something stupid instead. Then Bruce would be suspicious and force it out of him in a couple weeks. That sounded tedious.
He also considered casually mentioning it on patrol. Upon further thought though he realized that no matter Bruce's actual opinions he'd probably just get a "hm" response and then he'd Batman away. Maybe even give him a comment about distracting conversations on patrol.
He was just determined to let the moment come to him despite how much that went against his nature. Fortune favored him and actually provided him with a good moment. It was after patrol on a quiet night when the pair wasn't quite ready to return to the manor yet.
They were sitting on the edge of the Gotham clock tower watching the city move languidly in the night. It would be a horrible moment to ruin, but Tim couldn't think of a better moment. "Hey B, mind if I tell you something? It's not that important just something I thought I should share."
In spite of his efforts Bruce picked up on the hesitation in Tim's voice instantly. "I'm listening," was his only response.
"I'm bisexual," Tim looked away into the skyline because he was scared of what he might see on Bruce's face. The cowl covered a lot, but after being Batman's partner for so long a mouth twitch could be very telling. "We don't have to talk about it ever again. I'm not going to bring it up if this upsets you. I just didn't want to hide something from you," he continued. He probably would've kept rambling once he managed to catch his breath, but then Bruce decided to speak.
"Robin."
"Yeah?"
"I'm not upset. You can talk about your sexuality as much or as little as you're inclined to," he affirmed. This finally got Tim to look at him. "Your identity would never affect your place as my partner or my son." The words looked like they had to be pushed out of his mouth. Not because they were lies but because it was more honest than Bruce liked to be.
There wasn't much more to say after that. Tim made a positive hum sound and nodded. They looked at the city for a little longer then returned to the manor. The night stayed quiet. It was something Tim had dreaded when he first imagined coming out; being enveloped in an uncomfortable silence. This felt nice though. He was relishing in finally saying what he had to say.
It was only when the pair was about to go their separate ways towards their rooms that Bruce brought it up again.
"Tim?"
"What's up?" Tim turned back to his dad.
"Did I ever do something that made you afraid to come out to me?"
Tim thought about it, he tried to conjure up any moments that made a part of him tense or itch. Nothing came to mind. "Honestly I think it was mostly in my head. I knew you wouldn't hurt me or anything—I wouldn't have told you while on a clock tower if I had—but I just couldn't get the idea out of my head that you'd be disappointed." He shrugged it off as if the idea hadn't kept him up some nights.
"I'm not disappointed," Bruce clarified once again.
"I know," Tim smiled, "Oliver told me you wouldn't be too."
"Oliver? As in Oliver Queen?"
"Yeah. He seemed like someone safe I could tell that knew you well enough to assess how you'd respond."
Then Tim just walked to his room leaving Bruce to be stunned by this news.
—
"I hold a deep resentment towards you," was the first thing Oliver heard when he picked up Bruce's phone call.
"I resent you too, you're calling me at midnight," he yawned.
"Why would Tim come out to you before me?!" His yelling was only a whisper, but his frustration was still evident.
"Probably because I'm well known to be an open minded individual while you like to remain mysterious," Oliver mocked him. "Hey, honestly asking here, why have you never come out to your kids? Like obviously you don't have to, but I doubt any of them were severely homophobic nine year olds."
"First of all, Tim was older than that when we met. Second, if it was up to me my kids would know the same amount of my love life as the paparazzi; except they of course would know it to be fake. However Selina lacks tact and there's living proof I was with Talia," he began to list. He paused,"Lastly, I honestly kind of thought they'd all just figure it out," he admitted.
"Right, because the average kid speculates their parent's sexuality."
"Dick might've figured it out, but I think it was just his wishful thinking when he asked if I was with Clark one time. Even when he knew we weren't dating he'd say, 'I'm gonna go to my better adopted dad's house' when he'd get mad at me as a kid," he recounted.
This made Oliver laugh so much he was scared he'd wake Dinah up. The rest of the call mostly consisted of Oliver gloating over the fact that Tim had trusted him more. Then right at the end Bruce asked him to name any LGBTQ+ charities Oliver would recommend he donate to, and Oliver promised to send him a doc with the info once it was actual morning. "With sunlight and chirpy birds," Oliver described.