What's the best part about dating a homeless women?

You can drop her off anywhere.

This joke may have profanity.
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How do you know a homeless woman is menstruating?

If she's only wearing one sock. (This joke brought to you courtesy the homeless guy outside my local 7-11.) Edit: tweaked the punchline.

What's the best thing about dating a homeless woman?

When ur done, u can drop her off anywhere.