Off the top of my head, here's a few things I regret:
Had a buddy who's roommate bought a $1000+ mountain bike. He was really careful about never leaving it out and always had it locked up. One day my buddy comes home and notices that his roommate left his bike out in the back yard and was gone to work. He called me up and I came over with my truck and we took the bike and stashed it. His roommate came home and he played dumb. My buddy took the bike later and sold it and I was supposed to get some of the money but never did. Still, I always felt shitty about participating.
Had a class in business college, Credit 101 or some shit. Turns out the entire grade was from weekly quizzes and a midterm and final, all multiple choice. My bro took the course the semester before me and he kept every quiz and the midterm. You got the test back to go over it but then you had to pass them back in (small question bank I guess). My bro just kept his tests and never got caught. He gave them all to me and sure enough, the tests were all identical. I intentionally got a few wrong each time to not cause suspicion but still, I was tops in the class. Had a couple of close calls as the teacher made references about asking me about a certain concept when others were having trouble understanding them. I was lazy, I read none of the material, did none of the homework, never studied, just showed up for the tests with the answer key! Well, turns out there was an academic award of $1500 donated by some bank for the top grade in this class and I won it. I was supposed to do some big thank-you letter to the bank but I never did, I just cashed the check and spent it.
Went on summer vacation without my girlfriend cause she had to work or something. Ended up cheating on her with some girl we both knew. Of course, she eventually found out and it devastated her. We broke up shortly after and I know I hurt her so bad. This is one of the things I regret the most but it was a valuable lesson, I have never cheated on another girl since.
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