A Gentleman's Choice is when you pick up both a mother and a daughter, at different times, and must then make a choice between the two at a later date.
Raul met this chick at the tailgate party and hooked up with her that night. The next weekend, he picked up a cougar and woke up in the same house as the weekend before. Over the course of the next week, he had to make a Gentleman's Choice about who he was going to see next weekend.
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