This is exactly why I am so conflicted. That extra 5% comes from me wondering if, as part of his "ultimate troll," he just decided to ask a question just like he always does but instead make his situation/responses sound absurd.I'm confused about what you're suggesting here. You're saying that you think he's being sincere with most of his advice threads, but that he's trolling only with the dating advice thing? I'd say that's the *least* likely possibility. IMHO, either he's being absolutely sincere about everything, or his entire forum persona is an act. I say that because his other "advice" threads are also ridiculous, just not quite as ridiculous as the dating one. I mean, in the "How do I meet the president?" thread linked above, he asks about how to schedule a private meeting with the president, and in another thread from last year, he was asking about how to get appointed to the Cabinet. All of his postings about his personal life are rather whacky, and his political posts are also not terribly sophisticated.
He does not seem to be sophisticated or self aware enough to pull off a "joke" like the dating advice thread. So either he's being absolutely sincere about the whole thing, or else he's not really the person we think he is from his posts here, and he's being "fake" not just in the dating thread, but in the rest of his posts as well.