With three words, four shots, an affair began

Yale Hollander is a dad, husband, legal professional and writer whose works have appeared in a number of local and national publications. He is currently a trustee of the St. Louis Jewish Light, however the opinions and viewpoints he presents in this blog are strictly his. Follow him on Twitter @yalehollander.

By Yale Hollander

The old cliché is true – you never forget your first.

I still think back fondly on that chilly, late Autumn afternoon in 1992 when I looked a young woman square in the eyes and uttered those three magical words.

And those three words were, of course, “one Sledgehammer, please.” 

The Sledgehammer was a four-shot latte. Its nickname came courtesy of the Yippee Yi Yo Café (no, I’m not making that up), a coffeehouse in Oklahoma City (now the name makes more sense, right?). The “Triple Y” as it became know to my fellow law students and me, had been open only a matter of hours when I crossed its threshold, in dire need of a caffeine infusion. 


I was the first customer to order a Sledgehammer and the shop’s proprietress was gleeful that someone was willing to take a chance on what, in that pre-Red Bull era, was considered an extreme beverage. If I recall correctly, she wished me good luck as she handed me my order and I headed off for bankruptcy (the class, not the financial state). 

The affair was on — with the coffeehouse, that is.

For the next seven months, the Triple Y was a daily refuge, and not just a refuge from the dreadful brew corroding the urns in the student commons or the equally bad stuff dispensed in the law review office (no, I wasn’t a member, but one of my very close friends was the editor-in-chief and association has its privileges, such as they were, or in this case, weren’t.) 

The Triple Y was a pleasant place to start the day on my way to campus. It was a relaxing venue with an expansive front porch where a handful of my buddies and I would enjoy after-dinner coffee and cigars while listening to Ol’ Blue Eyes croon during the establishment’s self-proclaimed “Sinatra Saturday Nights.” Twelve or so hours after that, it would serve as the quiet haven for coffee and the Sunday paper.

That first affair was like a ristretto espresso — intense, but brief. I graduated in May and moved back home to Missouri. That summer, I struck up another relationship, this time with Lakota Coffee Company in Columbia. It became my morning and lunchtime outpost while attending bar exam review classes. But that relationship, where I discovered the French press and Sumatran beans, was also a mere matter of months in duration.

I moved to St. Louis in October of 1993 and became a coffee vagabond for a few years, drifting among the various — and frequently short lived — caffeineries of downtown Clayton where I worked. 

And then, at the turn of the Millennium, IT arrived.

IT, as you may have guessed, is the Big Kahuna of coffeehouses; the one with the green mermaid; the one that unleashed Pumpkin Spice Mania upon society. And IT plopped down a rather large shop within a very convenient walking distance to my office. IT became my second office for the four subsequent years I remained in Clayton.

I changed jobs in 2003, relocating to Earth City. Shortly after that move, IT opened a shop a mere five-minute drive across the Blanchette Bridge. That relationship spanned nearly six years.

Next came 2010 when I spent a period of “involuntary self-employment” holding forth at the Kaldi’s in the Clayton Crescent, as I did some column writing, freelance consulting and pursued the Next Big Thing. 

When the Next Big Thing struck in the late summer of that year, I was back in the grips of IT, this time an outpost at Westport Plaza where I have been for the past four and a half years. 

I have enjoyed my stay there. The staff is friendly and competent (a prized combination in coffeehouses). And they have one of those mega-expensive, newfangled vacuum pump coffee extruder thingies that brews you a cup of joe strong enough to give you the sensation that I can only assume is how Vladimir Putin feels all the time.

But this relationship too is coming to an end. Next week, my office relocates to Town and Country and I will need to find a new venue for caffeinated diversions. As of now, the frontrunner is an outpost IT operates on Clayton near Mason Road. 

I’ve patronized that shop before. It’s pretty small and lacks the fancy-pants extruder contraption, but if there’s one thing I’ve learned about relationships, it’s that it takes sacrifice and understanding to make them work. 

I shall (French) press on.