By John Semley

A lot of people do a lot of weird stuff on the internet, and ground zero for commercial e-weirdness is Craigslist. In Declassified, Torontoist combs over our city’s listings to find the best (and worst) of the bunch.

Illustration by Roxanne Ignatius/Torontoist.

Things Torontoist will herein declassify: the heartbreaking loneliness of the middle aged comes in many, many shades. Also: MILFs are out. Bring on the DILFs!

Fifty-four-year-old men say a lot of things. But probably nothing ever written smacks of being written by a fifty-four-year-old man quite like: “I’ve paid my dues in life. I’ve got a receipt.” Presumably this receipt comes in the form of a small Lacoste alligator tattoo on the left pectoral, or a “fun” licensed Looney Tunes golf shirt with the Tasmanian Devil emblazoned over pectoral same. Perhaps we shouldn’t tease—anyway he’s pretty explicit about not wanting our judgments—because there is a kind of modest, compromised honesty in wanting nothing more than to find people to help you mount a cover of Alice Cooper’s “No More Mister Nice Guy” that you have personally arranged (probably to make nicer, if anything). So musicians, if you’re reading this and want to jam with a guy who will use his personal computer as an ad hoc P.A., contact this dude. One thing’s for sure: he is not from Mars.

As Canadians, we always love a nice “Joe From Canada” joke. And looking for so-and-so from Toronto is the next best thing. But again, we’re posting this a legitimate call to action. If any of you know Scott (no last name) from Toronto, please help these people find him. Now, we don’t know much about Scott, except that thirty years ago he was twenty-four, which puts him at “approximately” fifty-four now, assuming he ages at the standard rate of one year per year. What a sec. Fifty-four? Could Scott from Toronto be the guy in the post above looking to start a bar band? Starting a bar band does sound exactly what a fifty-four-year-old guy who was a lawyer but then become disenchanted with “the lifestyle, man” after he made a boatload of money would do. Scott from Toronto, there may be gig in Tennessee lined up for you, bud.

Ever since American Pie popularized the term—holy crow, eleven years ago? Christ, I’m old—we’ve been living in a world of MILFs. MILF porn, joyless direct-to-DVD teen sex romps, cougar parties, Cougar Towns even, your mom using the word “MILF” with the same strained faux-hipness of her using the word “The E-mail” and thus making you feel so dirty and embarrassed that four turpentine baths can’t get you clean: it’s all around, these MILFs. But what about the dads? All these moms are getting ogled and fetishized while all the middle-aged fathers just sit around getting fat and dreaming about covering “Rock ‘n’ Roll Suicide” with a bar band. Well buck up, DILFs, ‘cos some people like you. Like this guy, a spry twenty-nothing who caught a glimpse of a DILF at a book fair, of all places, and tries desperately to bridge the age chasm via Craigslist. Could this be the sign of a new era? The age of the DILF? If it means sixty-six-year-old Craig T. Nelson re-inserting himself into the culture as a broad-shouldered symbol of male sexual potency, or a considered reappraisal of the Tim Allen canon, then we say bring it on.

This to me is just about the most heart-wrenching thing I’ve ever read, and not just because my mom’s name is Fran (and, sometimes, Frannie). The idea of this jet-setting pilot returning regularly to Casey’s roadhouse-style eatery adjacent to a Travelodge near an airport is too much to bear. Imagine flyboy, slumping in like clockwork every week, taking a seat at the bar, ordering a reasonably priced domestic draught himself and an “exotic” Lychee Berry cocktail for the woman who will never arrive, his head snapping towards the door every time he hears it swing open, only to find another group of jet-lagged business types. Week after week our lovelorn captain, master of the sky, lowers himself to choking down an appetizer order of Chicken Pecan Lollipops and an entrée of chicken fajitas, the steady sizzle of the sautéed vegetables his only real companion. That and the chatty Latino or Spanish waitress, biding her time to play cupid in this despairing missed connection. But perhaps her story is better left untold.
Find listings we should include in our next edition? Email them to declassified@torontoist.com.