Last week I fulfilled my obligation as a Jew by apologizing to eight people. Only one forgave me. Apparently I’m that much of an asshole. The rabbis tell us that we must seek forgiveness directly from people we’ve harmed. Many modern Jews have diluted the confession to a half-assed “please forgive me for anything that I may have done intentionally or accidentally, that you may or may not know about.” Some have even stooped to anonymously blogging their apologies. But this gets you no Judaic brownie points at all: the rabbis are clear that it’s not enough just to say you’re sorry. We’ve also got to tell the person exactly what we did wrong.

If the person refuses to forgive us—which is virtually guaranteed if we apologize on an anonymous blog—we have to ask again on two separate occasions so that God will give us credit for trying. Maimonides says it’s best to repent in front of witnesses, but in true Generation Y fashion, I sent the majority of my apologies via Facebook’s messaging system. Here are the results of my experiment in groveling for absolution.

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Star-crossed lovers: Freshman year can be so cruelGirl Whom I Dated Freshman Year of College: She lived on my dormitory floor. We hooked up after I convinced her to cheat on her boyfriend back home. (She turned her photographs of him facedown after we messed around the first time; this actually almost made me feel like an asshole.) I comforted her on 9/11. But she wouldn’t have sex with me after a couple weeks of dating, not even in the wake of the first terrorist attack on American soil—not even the oral variety—so I dumped her.

My Apology: “Wow, I was a dick to you freshman year, huh? I can't imagine you remember me too fondly but I've definitely mellowed and I try to treat people a little better, and women with more class, so for what it's worth.... I hope all’s well with you.”

Response to My Apology: No response.

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The old sock-on-the-doorknob method: Essential for roommate harmonyMy Roommate Freshman Year of College: An Orthodox Jew. We had absolutely nothing in common. He never brought girls back to the room because of his religious beliefs and therefore refused to work out a “sock on the door” system, subsequently walking in on me and the girl whom I dumped after 9/11, not like it mattered because we weren’t having sex anyway. In retaliation I masturbated in our room while he tried to do homework, and I once smoked a cigar with the window closed, which triggered his asthma. (The stench seeped into everything: clothes, towels, sheets, toothpaste. He had to sleep on a couch in the student lounge for three nights. I did too, and I don’t have asthma.)

My Apology: “I definitely was a prick to you freshman year and probably could’ve handled the situation with more maturity. I hope that’s all a distant memory for you and that all is well in D.C. or wherever you’re living these days.”

Response to My Apology: No response.

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How many apologies?: Maimonides recommends threeGirl Whom I Made Cry in High School: On a class trip to New York sophomore year, a bunch of my friends spent the night in our hotel room talking dirty about chicks. We didn’t know that the girls were eavesdropping on our conversation through the door. At one point I compared two of them thusly: “[Girl #1] should give her tits to [Girl #2] because they’re totally going to waste considering her troll face.” Girl #1 spent the night sobbing in the stairwell. The other chicks forced me to apologize, but frankly she should have apologized to me for spying.

My Apology: “I'm sure you remember a certain incident on our New York trip. Well, I still feel pretty bad about that one, so I hope it didn't cause any long-lasting psychological trauma and you've long since moved on. I hope all is well w/ you and look forward to your response!”

Response to My Apology: No response.

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African-American Friend to Whom I Made Offensive Comment: His mother drove us home when we were in junior high since we lived in the same neighborhood. I honestly do not remember saying this—and frankly I have trouble believing it—but apparently at one point I rolled down the car window and screamed, “HELP! I’M BEING KIDNAPPED BY A BLACK FAMILY!” (Hey, at least I have an African-American friend… well, at least I did.)

My Apology: “Holy shit, did I really say that?!?!?!?!”

Response to My Apology: No response.

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Whisker sour: Would you forgive?Girl Whom I Mocked for Having a Mustache: In her words on my Facebook wall, “Last time I remember talking to you I think I was still in junior high and you were making fun of me for having a mustache. It was a pretty good time.”

My Apology: “Wow, I am a dick and I am sorry! How’s it going?”

Response to My Apology: No Response.

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"I'll tell YOU when I've had enough!": Yes, you have to repent for things you don't rememberGuy Whom I Insulted at His Own Party: My girlfriend and I were invited to a house party a year ago. I had never met anyone in attendance but she knew a bunch of people from her classes. I had a bit too much to drink—Tanqueray Rangpur, truly vile shit—and whispered in the host’s ear, “I know you’re a fucking pervert, you sick motherfucker; I can see it in your eyes.” As I was dragged out after a litany of subsequent accusations, I kept screaming, “You’re a fucking pervert; I can tell it, you sick son of a bitch.” My girlfriend covered her face in shame but had a wonderful time the next morning with her favorite game: Do You Remember What You Said Last Night?

My Apology: “I guess that was a pretty bad first impression. Just because you’re a Catholic doesn’t mean that you’re a pervert.”

Response to My Apology: No response.

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Party fowl: But it led to love!Friend Whom I Cock-Blocked for Love: I met my girlfriend four years ago at my friend Greg’s nineteenth birthday party. He had a crush on her, which I knew—and he had recently lost fifty pounds in an effort to make himself attractive to females—but she and I had amazing chemistry from the beginning and wound up in bed together that night. Anyway, my friend actually cried over it because he really liked her and really trusted me, which was a pretty big mistake on his part.

My Apology: “That was wrong, man. I betrayed you…I betrayed ‘bros before hos.’”

Response to My Apology: “I accept your apology. If you hadn’t taken her, I wouldn’t have met [my long-term girlfriend], so it all worked out for the best. Plus you’ll never forget to wish me a happy birthday.”

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Total landmine: Approach with cautionMy Current Girlfriend: A week ago she suggested that we should have pizza for dinner. “We haven’t exercised once this summer,” I said. “Don’t you think we need to lose some weight?” (She has commented for months that we need to lose weight, but God forbid that I acknowledge the same thing.) “What do you mean WE?!?” she bellowed, proceeding to not speak to me—or acknowledge my existence—for the next four hours, until I walked into the bedroom buck-naked, flexing my biceps and jiggling my flabtastic belly, also known as “the Lovechild.”

Response to My Apology: Orgasm sounds.

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So there you have it: Eight apologies, only one absolution. Maybe Maimonides was right about not using Facebook.

[This article has been edited since publication.]