Dear Captain Obvious: I’m sick of being good. I miss the days when I gave underage girls STDs, burned people alive and everyone hated me with a passion. Now that I’m married and walking the straight and narrow, life couldn’t be drabber. What can I do so spice things up? Bad Boy.
Dear Bad Boy: Hhmm, let me think. I don’t know how you can get any more exciting than murder, that’s really up there on the list. I know! Kill two miserable birds with one stone by strapping 20 lbs of C4 explosives to your chest and walking into Jabot Cosmetics. Word around town is they’re on the verge of financial ruin (again!). Make sure to go after hours—no sense taking innocent lives.
Dear Captain Obvious: My daughter is ashamed of the fact that I’m a housekeeper. No matter what I do or say to brighten her day she never misses an opportunity to treat me like something that just crawled out of a cesspit. I don’t understand it. I’ve given her everything, everything but the maid uniform off my back and yet nothing seems to satisfy her. How do I get my daughter to love me? Heartbroken.
Dear Heartbroken: It’s time your offspring learn that earning a decent living is nothing to be ashamed of. The next time she gives you the stink eye give her a good open-palm slap across the face. While she recovers from the shock of seeing you grow a spine, tell her you love her, but if she ever looks at you cock-eyed again you will make her regret the wretched day you brought her into this world. She’ll thank you later.
Dear Captain Obvious: I put the “ass” in Jackass and it’s a little known fact that I absolutely adore exposés! So, I decided one day to get involved in starting a new fashion magazine with, get this, my ex-wife and her husband. Trouble with that was we couldn’t agree on anything. Not how to dress our models or how to exploit my partner’s family to boost our financial gain. Now I have unemployment to contend with as a childish coin toss bet left me agreeing to relinquish my stake in the business by accepting a buyout. Then, to add insult to injury I later discover that this purchase was made possible by my partner’s father, a man I despise more than anything. As you might expect I now have to make him pay. It’s my life’s purpose—my sole reason for existing really. Player Hater.
Dear Player Hater: As you might expect I laughed uncontrollably after reading your letter. What kind of a buffoon sells a company by tossing a coin? Extra points for getting into business with your ex-wife and her husband. It sounds incredibly cozy. You know what else sounds cozy? Me throwing your letter in my fireplace and warming my hands.
Dear Captain Obvious: The other day I was brazen enough to declare my feelings for my best friend’s ex-husband to her face over an afternoon tête-à-tête at our favorite hangout spot. There I was committing the one sin that one woman should never do to another and yet I felt completely calm and relaxed. It was as if I was telling her that I was borrowing a hairbrush or her favorite shade of lipstick. If sampling my best friend’s sloppy seconds is wrong then I don’t want be right. She seemed fine with it, but how do I make sure that I haven’t overstepped any boundaries? Frenemy.
Dear Frenemy: Poaching ex-husbands are not for the faint-of-heart, my dear. You must be willing to sink to the lowest levels possible, unhindered by conscience or basic human decency. If you feel you are ready, truly ready then my advice would be this: the next time the three of you are in the same place together conduct some sort of lewd act upon him. If she doesn’t bat an eye you have confirmation that you are living in some sort of parallel universe where this sort of reprehensible behavior is acceptable.
Dear Captain Obvious: The man who I only just found out is my biological father a mere six months ago, took me into his life and gave me the keys to his wealthy kingdom. I was given a plum job in his multi-conglomerate, a room in his fancy mansion and access to all the servants I could order around. Whereas any other person would show appreciation I chose to be a complete douchebag, and guess what? It backfired! Nauseated by my betrayal my father promptly ejected me from his life and instead of slinking away quietly in shame I chose to be dragged out like road kill off of a desolate highway. What should my next step be? Bad Seed.
Dear Bad Seed: You mean besides crawling under a rock and shriveling up? Gee, not sure… try harvesting some humility, that might do the trick.
Dear Captain Obvious: I’ve found recently that being rich can be quite boring so I thought it might be a good idea to ask my parents if I can forgo my blue-blood education for public school. It took a little bit of finessing, but I got them to agree to what will most certainly be my undoing. From what I’m hearing I’m in for a real treat; metal detectors and little to no funding for school equipment and learning materials sounds like a student’s paradise. Add to that, overcrowded classrooms, gang violence and dance offs that turn deadly, and you have the type of learning environment that dreams are made of. Do you think they would approve of me getting a tattoo and shaving, “eat me” into the back of my head? Growing Up.
Dear Growing Up: There comes a time when a boy must break away from the homestead and get himself into as much trouble as humanly possible. It’s your right and your duty, young man. Though I would hold off on the body art and carving of marketing slogans into your head, I would definitely seize any and every opportunity to be stupid. If you didn’t do that people would begin to wonder what was wrong with you. Don’t let them down.
Dear Captain Obvious: It’s almost too good to be true, but I finally got the recognition at work that I’ve been toiling away for all these years. That’s right, my days of saying ‘No, sir’, ‘Yes, sir’, and ‘How high, sir?’ have finally paid off. Now the boss’ kids work for ME, and I get to sit in the big man’s chair (the very same chair I used to squat under and wait, faithfully, for my orders). I don’t have anything in writing or a contract but, that’s okay, a handshake is all I need. Movin’ On Up.
Dear Movin’ On Up: There’s nothing quite like the lull of a false sense of security, is there? It’s quite magical actually. Enjoy it while is lasts, my friend. You’ll be back under that chair again someday, I can assure you.
Originally published: Sep-14-2008
