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I say "Gay".
A man asking for another man's haircut? Really?
Most people that watch Mad Men and expect greatness will not continue with the show. It's one of those shows that you have to invest your time in to get the most out of it, and for those that do choose to invest in it, it really pays off from the second half of season two and on.
As for the OP, no it's not gay. Although a hairdresser may not know who Don Draper is, since they'd probably be one of the aforementioned people that won't invest time into the show. It's a pretty normal haircut though for men with long hair; most just don't style it like that.
I say "Gay".
A man asking for another man's haircut? Really?
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