I think the rainbow wig sends the wrong message to a girl you might be interested in.
I'm not really a hat guy, so I don't know. If it gives you confidence, go for the Assuie hat.
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I plan to make the best of working with Melvin. I know I'm not going to be able to confront him outright, because he's just going to tune me out, but I plan to establish myself as someone who knows what he's doing and knows how to focus on a task to get the job done well. That will hopefully be enough.
If I were in a group with you, I would probably use that strategy.