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Of course, romantic relationships are the easiest and best places to overflow your life with regret. Let's say you meet someone online; make sure you openly profess your admiration and love before ever meeting them for real. Then, when you meet them in person and equate the experience with double-ended food poisoning, think back to the ridiculously glowing emails you sent and regret every action that led to your parents meeting, getting married, and deciding not to abort you. Essentially, you should regret getting into relationships, continuing relationships, and then getting out of relationships. And then, later, getting back into the relationships you already got out of once.
When it comes to the rest of your life, aside from school choices, job choices, and housing choices, your innate guilt and fear should keep you from making any hugely bad decisions, like robbing the preloaded-gun store. Instead, you should focus on regretting smaller things, like the outfit you chose to wear today that you weren't sure matched and are now totally conscious of every time someone looks at (and undoubtedly judges) you. You should also regret buying that plant you saw at Home Depot, because as you watch it slowly die, you realize you already knew you were incapable of sustaining life. As you bury it with tears of regret streaming down your face, promise yourself you will never kill another plant by owning it. Then go out and adopt a puppy.
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