To observe that Valentine’s Day is a crass, stupid, bourgeois, tacky, irrelevant, hypercommercial, saccharine atrocity of a holiday, only taken seriously by maudlin, sentimental nitwits with horrible taste in life, is to indulge oneself in—and not to put too fine a point on any of this—a desperately boring cliche. It’s nowadays possible to simply throw out one loaded-down workhorse of an epithet, “Hallmark!,” and put the issue to pasture. The resistance movement isn’t much more inspiring; people who’d rather not, don’t, and just get plastered with their friends. They call these Anti-Valentine’s Day gatherings; we call them, you know, weeknights. Unless they happen to fall on weekends, in which case we adjust our vocabulary accordingly.

(Not to say that we’re above organizing our own Anti-Valentine’s Day affair. We’re not.)

None of the stories herein are really about V-Day, thank god. We believe them to be true, but they’re mostly from readers, and we have no way of establishing their veracity—they say all’s fair in love and war. We also had to do some trimming because of issues of boringness and/or sexism. So you’ll miss, for instance, the one about the guy who “was at a traffic light when [he] saw some of the biggest breast in the city of Chicago.” It ended happily enough—though contrary to what you might think, the rest of it was not about the narrator going off in search of the other breast. Then there was the guy who was hot on the trail of “the kind of U of C girl who struts about in tight pants and leather boots and who wears on her face a sexy little mask of bitchy disdain.” And that was when he liked her! The story ended badly. She was just not that into him.

Anyway, those tales aren’t here or online, and you’ll be happy to know that the biggest breast in Chicago has since been confiscated and returned to the Woody Allen movie from whence it sprang. In these pages, what you’re set to read about involves, in no particular order of importance: broken bones, cigarettes, dick pix, dying alone, nerds, missed connections (sorry, that’s proprietary; we meant “I Saw Yous,”), and drug dealing. And more. You’re fucking welcome. —Sam Worley

“Dear Elsa,” by Rose Tully

A letter to first loves, cigarettes, and Chicago

How Not to Hook Up

Tales from the Continental’s den of 4 AM iniquity

How do you like them Apples to Apples?

A dating event devoted to geek love

Defining the #perfectcompanion

Some of our favorite responses to our @Chicago_Reader entreaty: Tweet what makes yr ideal mate

Let us indulge your inner stalker

The Reader responds to some of our favorite, creepiest, most stalker-ish I Saw Yous

Got a clever response of your own? Post it here.

Tales from the dating front

Readers submit their stories about an underwhelming Johnson, an overwhelming leisure suit, a long-lost Parisian love affair, and more