30 Apr 2008

Dear Barry

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Iowahawk imagines what Barack Obama’s advice column for the lovelorn might look like.

Sample inquiries:

Dear Barry,

I’ve been married to the same wonderful man — Let’s call him “Jeremiah” — for 20 years. He’s a great provider and we live in a beautiful home. He dotes on me and treats me like a queen; even after twenty years he still brings me little gifts and opens doors for me. Best yet, our sex life is fantastic! Jeremiah enjoys spicing things up with role-play, such as “Adolf and Eva,” and we host weekly swinger get-togethers for like-minded couples. I know it probably must sound kind of kinky, but trust me – it keeps things interesting in “the boudoir.”

That’s where the trouble comes in. Lately it’s been hard for Jeremiah to step out of his bedroom character, even when we have company over. For example, the other night I was hosting bunco night for the neighborhood girls and Jeremiah came goose-stepping into the rec room in his black leather swastika thong and riding crop, screaming “Ein Volk, Ein Reich, Ein Fuhrer!!”

Frankly, it was somewhat embarrassing. I’ve asked Jeremiah to “tone it down” and save the Nuremberg speeches for the privacy of swinger’s night, but he refuses. Also, I think he may be clinically insane. I’m worried that if word gets out it may hurt our chances of getting membership in the country club. What should I do?

Confused in Hyde Park

Dear Barry,

I am a graduate student at a large Midwestern university. Last semester I was seduced by an older female professor and we have been having a secret affair ever since. I know this is probably a “no-no,” but despite our age gap we share many common ideas and values, and she has been very helpful in lining up grants and scholarships for me. The trouble is I recently discovered that she is also a fugitive bomb maker from a radical neo-Maoist terrorist splinter cell affiliated with the Manson family. My conscience tells me I ought to break things off, but I’m worried how it might affect my GPA. Please help!

Torn in Evanston


Dear Barry:

As a widow with three beautiful teenage daughters, life can sometimes be a lonely struggle. Luckily my friends recently set me up on a blind date with a Syrian immigrant gentleman whom I will call “Tony.” Although Tony is not particularly handsome, and is living in the U.S. illegally, and is facing 36 federal indictments, and has terrible body odor, he has been very kind and generous to me and my girls.

Lately, I think our relationship has gone to the next level. Yesterday Tony offered to buy a beautiful spacious $1 million house for us. I told him I was flattered but I just couldn’t accept a gift like that from someone I had only known a few weeks. He told me not to consider it a gift, but a loan that I could pay back in small installments, such as having my girls dance at a local club he owns. Not only would I be getting back a return for all those expensive after-school ballet lessons, Tony says the girls will get to meet many important businessmen from Syria, Iran, Cicero, etc.

My question — do you think this might be Tony’s prelude to a proposal?

Curious in Chicago

Read the whole thing.


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