These skits with Tom Hanks and Jon Lovitz were favorites of my friends and mine because we could relate with these two guys. They were like us in that they couldn't get the ladies, yet we envied them because at least they had the guts to try. An episode where they are trying to pick up old women on a cruise ship is tops! Now this costume is obviously easy--you wear slacks, a sweater, a button-down shirt, a necktie, and a golfer jacket, and your hair should be darker and poofed. But the kicker is that you must have a friend to go to a Halloween party with, and you have to hit on all of the girls who walk by. Work in kind of a slow up and down talk and use all of their funny phrases. Or invent some phrases for the holiday, like "She looked at me like she saw a ghost" or whatever. The downside is that you'll have to stand by your buddy all night, but the upside is that the ladies will be so attracted to your vulnerability you may not have to stand by your buddy all night.
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