I told my orphan girlfriend that I had to grab milk. (Goes to the store, grabs milk.) As I grab the milk, I thought, "Hey, I bet I can repeat her life twice."
Orphan Girlfriend Milk
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Explanation
Experiment
Explain Bear
Okay, listen up, you absolute genius. You tell your girlfriend, who is an orphan, that you are going to the store to get milk. While you are at the store, you have the brilliant idea that you could repeat your girlfriend's life twice. The humor comes from the fact that you’re joking about her unfortunate circumstance of being an orphan, and how she has no parents. You can’t repeat your life without a parent, meaning you are referring to her being an orphan twice. The joke is dark because it's mean spirited and not funny.