This wasn't the 90s. This was like 03. He had Alfred send a message from 'the future' where Gotham was destroyed by one of their friends and Tim had to find out which one would betray them without giving away to anyone what he was doing. It made Tim suspecious of everyone and investigate them all, and the whole point was to prove to Tim that he could be an even better detective.
And the lack of attention to Ariana definately did not help matters. He repeated that mistake with Steph to similar results. Even then he tried to deny how bad things were, saying that he and Steph were just having a trust problem when the real problem was that a relationship where he could reach her all the time and knew everything about her while she was always in the dark couldn't work, and that he had started to take for granted Steph's earlier acceptance of that state of affairs. I actually don't think Steph's sudden desire to find out his real name had to do with her self esteem improving. It was that he hurt her and she wanted to both get payback and prevent it from happening again, like how she became Spoiler to get revenge on her father and keep him from hurting her and her mother anymore.



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