Tim's never regretted his decision to go to Barbara Gordon when Batman began to fall apart after Robin's death. He does reserve the right to complain when strange men in masks begin to use him as an intermediary for Oracle though. Series

Tim gives him an incredulous look. "Is this really the way you guys do things? I'm sorry, but do you really think it's okay to marry someone you barely know and create an entire person—a baby, one that's going to need someone to look after it for 18 years or longer—just for money?!" "That's not…" Jason makes a frustrated sound. "Look, you're 19, right? We can talk about the intentional baby acquisition when you're legally old enough to drink. By then we'll know if our marriage can sustain a child. But I think it's worth a try." - After civilian Tim Drake gets trapped in the Bat Cave following multiverse shenanigans, he enters an arrangement with the crime lord Red Hood in an effort to gain access to a trust fund with some very particular requirements.

Tim Drake leads a...mostly normal life, helping people get the best insurance they can afford. Soon though, he finds himself embroiled in a plot that involves Robin trying to take him down, and Batgirl possibly helping. Add to the mix Red Hood using him for information, and a strange young man walking into his office under false pretenses, Tim finds that his mostly normal life is about to completely change. Tim knew there were worse jobs in Gotham than insurance agent, but he’s hard pressed to think of another at the moment. As he shoots off an email to a client about looking into their claim asap, he hears the glass door to the small insurance office open and watches Stephanie Brown,the goddamn Batgirl, walk into the agency and catch his eye. He puts 'masked vigilante' at the top of the list.