- In Robin #58:
Robin: Could I ask you for some non-professional advice?
Oracle: Talk to Doctor Babs, Robin.
Robin: I have this friend…
Oracle: Hold on. This friend isn't you, is it?
Robin: My friend is pregnant.
- In Robin 137, Tim gets a little frustrated with having to fight the Dark Rider every night.
- "Hello, Bruce? I guess you're also still out tonight doing what we do. No need to call me back when you get this message. I was just thinking about our methods and needed to vent. This revolving door situation with our villains has really gotten out of hand. We keep catching them so the powers-that-be can keep putting them back on the streets? Where's the sense in that? Frustrating to say the least. I was wondering. Can I shoot just one of them? Everyone knows we don't use guns, so no one would ever suspect us. Perfect crime, right? I'm pretty sure I'm kidding — this time."
- Tim trolling Ives and Hudson when he comes across them looking into something he’s investigating as Robin by playing at being some kind of territorial monster from the shadows, For The LULZ:
- Tim's Dad, stepmom, Ives and Stephanie are able to give him a surprise birthday for his sixteenth without trying to keep it a secret because he forgot his own birthday. He gets all suspicious of them all being over without him knowing in advance and doesn't even guess what's going on.
- In, Robin #171 – The Odds Against Tim was (accidentally) having a nice dream while on a date with Zoanne Wilkins:
- In one issue a group of heroes led by The Veteran (the invincible personification of Patriotism) is fighting their way across Bludhaven, which is filled with C- and D-list villains recently escaped from a prison, to get to Robin. One such villain, who appears to be made of straw, leaps out of the shadows and declares...
Wicker Man: Behold! I am the Wicker Man! Beware my power!
The Veteran: Oh for the love of... [pulls out and lights a lighter] Behold! I have a working lighter!
Wicker Man: ...I surrender.
- Tim rescuing Lynx III from a custody exchange. She's a "gorgeous" (Tim's words) gang leader or undercover cop, and since Tim's not sure which, and since she helped out during some of the chaos recently, he decides to free her, perfectly aware that he's probably invoking Foe Yay. Once on a rooftop, Tim starts thinking "I really should not be doing this," and continues to repeat the thought as Lynx unzips her orange oversuit's top and wraps her arms around his neck. She's so hot she gets him to shut up and twice ends his inner monologue before and after making out! And since she has some trouble with English (not a lot) she drops several Double Entendre -filled sentences, ending with "Is going to get harder," which just forces Tim to say "Huh-?"
- Bruce then starts giving Tim advice on how to deal with you Cat-themed villainess...
- Later, she takes to tackling him out a window, so her gang believes they're fighting, then starts making out with him in mid-air.
- Tim discovering that Tam, panicking about Vicki Vale's questions, said they were engaged.