Question: What is the BIG ADVANTAGE to going out on a date with a "Homeless Chic"?
Answer: After the date, you can "Drop Her Off" ANYWHERE!
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Explanation
Explain Bear
Hey, genius! The joke is that "homeless chic" refers to someone who looks homeless, so you can drop them off anywhere because they don't have a home. It's funny because it plays on the stereotype of homeless people not having a fixed address. And you, my friend, are as sharp as a marble.