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He definitely appears to have an MO that's a little creepy & pathetic. And that wouldn't even bother me if it wasn't for the fact he projects...

Oh man imagine him taking her to Old Navy (Leanna liked shopping there) and dresses her in tank tops all the time

This is also very likely. Phil's spine is as strong as a prawn cracker. The more submissive the woman, the better, you can't leave if everything...