Dear Captain Obvious: Is it a bad idea to ask my fiancée for a little loan to pay off a really large debt? I feel so awkward asking so early in our relationship, but if she really loves me she wouldn’t think twice about it, right? Looking for a handout.
Dear Looking: You haven’t walked down the isle and already your beady eyes are glazing over at the thought of her checkbook?! The way I see it you’ve got two choices: be honest and ask her outright for the money and have her throw the ring back in your face (you probably didn’t even buy her a ring since you’re so damn hard up) or devise a clever plan to have her sign some papers when really it’s a transfer request to have the funds wired to your account). I know you’re thinking she’s too rich to miss it, but if she does, she’ll have your ass thrown in jail. Either way you’re screwed. Here’s a thought, why don’t you grow a sack, get a job and pay off your own debt?
Dear Captain Obvious: I just got married to a really wonderful guy who I love with all my heart. The problem is he doesn’t have a lot of money and I have it coming out of places you wouldn’t believe. I would love to stay at my dad’s mansion where I have servants at my beck and call but he wants to move back to his sparsely furnished loft downtown. I wish I could tell him how I feel but I think it would hurt his feelings (he’s insecure about his poverty). Any ideas on how I could broach the subject with him? Daddy’s rich bitch.
Dear Bitch: It’s not easy making a life work when the two of you are from “different worlds”, but, you’ve got to be honest with him or you’ll end up resenting his empty pockets. Just sit him down one day and simply say, “Honey, I’m going to hire an interior decorator and a housekeeper, this will free up my time to be more available to have sex with you. I really hope you’re okay with that.” It’s all about compromise.
Dear Captain Obvious: With the divorce from my controlling, insufferable, egomaniac of a husband finally over, I’m free to get on with my life. When I left the house we used to share I looked around and a flood of memories came rushing back to remind me of the way we were. He gave me pearls over a candlelight dinner of oysters, he gave me a chinchilla coat by the fireplace, and I could never forget the Christmas he bought me a company to run. Oh, how I wish I could quit him! Stuck.
Dear Stuck: What did you expect? You gave him the best years of your life and now you’re a used, empty shell. It’s time he upgraded to a newer, less wrinkly model. Hopefully your lawyers secured you a financial settlement cushy enough to buy some of your self-respect back. Cheerio.
Dear Captain Obvious: I live in a trailer in the outback and can’t really afford a decent meal but I have a really amazing jazz collection. The other day I got a surprising call from the nephew I raised him since he was a baby. “Crikey!” I says to him. The last time he called was to tell me that he found his biological mother, that she was rich and that he was gonna fleece her for every penny she had. That’s the last I heard from him, until last week. He called to ask me to give him an old Joe Zainul jazz record I had. He didn’t mention anything about our earlier plans and didn’t even offer to pay for it! He’s completely unaware that I grow weak from hunger with each passing day—it broke my heart, but I gave it to him anyway. He was all I had in the world, now there’s nothing left to live for. It’s only a matter of time before the coyotes get to me. They won’t get much: I’m just skin and bones.
Dear Skin and Bones: If you’re so hungry why not try pawning that rare collection of jazz records you have? Just a thought.
Dear Captain Obvious: Sleeping beauty has awoken from her slumber and left the building. My prayers to the Virgin Mary have paid off at last! No more bed pans to wash or bed sores to dress and screaming baby in the middle of the night to feed. Miracles really do come true. Vive la libertad!
Dear Libertad: I’m so glad you have one less person to bend and scrape for. How happy you must be. Honestly, I couldn’t care less. Bugger off.
Dear Captain Obvious: I slept with my best friend after getting wasted on booze and now everything is like, weird between us. He is like a brother to me. I feel so gross inside. This doesn’t make me a slut, does it? My friend was just as drunk as I was. My bad.
Dear Bad: Just because a whore falls down in the forest and no one was around to see it doesn’t mean it didn’t happen. I really wish I could help you, but something tells me this isn’t your first time and it won’t be your last. Just promise me you’ll try to wear a condom; we don’t want you and your drunken “brother” making liquored up babies.
Originally published: Feb-16-2008
