Fake Letters from the Imaginary Mailbag! "Allow me to introduce you to the 'Cate Blanchett' theory of relationships..."

Fake Letters from the Imaginary Mailbag! "Allow me to introduce you to the 'Cate Blanchett' theory of relationships..."
Dear OSM: Why do you call yourself Old Single Mom? You don’t look that old in your picture. Signed: Telling Readers Only Lies, Lady? Dear TROLL: About my moniker, I like to say two out of three ain’t bad. Heh. The “Old” is meant to be ironic – it was a tongue-in-cheek label I gave myself... Read more »

Did I really just ask myself, "What would Lorelai Gilmore Do?"

Did I really just ask myself, "What would Lorelai Gilmore Do?"
Hey! Late-to-the-Party Girl, here! I started watching Gilmore Girls this week, you guys! I missed the original Gilmore train. When the show premiered on October 5, 2000, I was taking it one day at a time after ten years of daily drinking. I was pretty sure those two chatty broads would make me want to... Read more »

Hey, Roxane Gay! I'm ready to abandon the 'Roseanne' reboot, now...

Hey, Roxane Gay! I'm ready to abandon the 'Roseanne' reboot, now...
Hey, Roxanne Gay. Remember me? The woman you don’t know from Adam who wouldn’t join you in boycotting the Roseanne re-boot just because Roseanne was a Trump supporter? Yeah, it’s me again. I promised I’d come back and report if I changed my mind about watching the reboot, so here I am.  So now if you’ll... Read more »
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I think I may be in a relationship with 'Alexa'

I think I may be in a relationship with 'Alexa'
I think I may be in a relationship with Alexa. She: Amazon robot  Me: Human being/Amazon junkie Not a likely match I admit but hear this: there is clearly something special going on between the two of us. This awkward realization dawned on me the other day when I was out in the world, pumping gas like... Read more »

I'm 18 years sober! (so where is all that "beyond my wildest dreams" stuff?)

Caveat: If you are in the first year of your sobriety, close this tab and go to a meeting. Nothing to see, here. Also: if you are in the first five years of your sobriety, subscribe to my blog at the link up top, bookmark this post, then come back in about a decade. But…if... Read more »

I think I saw God in the Chicago Park District this past Saturday

This past Saturday was the classically beautiful Chicago spring day that comes with a mandate: go outside and play! So my son and I took a basketball to a park near my house to shoot some hoops. As we approached the basketball courts, we saw a group of kids running and yelling and pushing each other around... Read more »
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"Did Ding Dongs always taste like crap?" and other pop culture musings

“Did Ding Dongs always taste like crap” was my original title AND subject of this post. But then I thought to myself, That can’t be your whole post, OSM. You’re a grown-ass woman with a writing degree. You can’t just write about Ding Dongs, silly lady. So I decided, instead, to use this week’s column... Read more »

Could the President of the United States do your job?

Could the President of the United States do your job?
I often wonder: Could the President of the United States do my job? This question is an informal rubric I use to grade the effectiveness of a POTUS’ leadership skills. I feel that the leader of the free nation should have the skills to do my job at least as well as I do it. ... Read more »

All Hail the Queen of Ridiculous Crushes!

All Hail the Queen of Ridiculous Crushes!
I used to believe people when they told me I was “just like them” in the Rodeo of Love. My friends used to assure me that they, too, found relationships tricky, and my oft-barren romantic landscape was not so unusual. But these days I’m more positive than ever that my experiences with romance are fundamentally... Read more »
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On the impending murder of my favorite tree (and the hypothetical Lifetime movie about said murder)

On the impending murder of my favorite tree (and the hypothetical Lifetime movie about said murder)
They are going to murder my favorite tree in a couple of months and I’m absolutely devastated.  I’m talking about the kind of devastation that has me crying so hard on my commute that drivers in the cars around me get uncomfortable if they catch my eye. ‘Willow Smith’ and I have been buddies for nine... Read more »