Then There Was the One About Greenheads Dating

Stop reading.

Stop, I said.

Why are you still reading?

It’s amazing, in a way, that you’re still reading.

This is the 300th time I have elbowed my way into the consciousness of unsuspecting readers as “The Outsidah.” Yeah, 300 columns. Sheesh.

I came up in Chicago in the days when great newspapers — the Tribune, the Sun-Times, the Daily News  (R.I.P.) — featured famous columnists: Mike Royko, Irv Kupcinet, Siskel & Ebert, the complicated Bob Greene. People on the train would say, “Did you see what Royko said today?” I wanted to be Royko! I still do. Of course, he wrote 7,500 columns in his lifetime, which puts me some 7,200 behind him. If you haven’t stopped reading yet, something tells me you’re not going to last another 7,200 rounds of this stuff.

But let us pause and consider who, or what, “The Outsidah” really is.

In theory, each of my 299 previous columns has offered something approximating commentary on life in small-town New England from the viewpoint of a newcomer.

In reality, I’ve basically just sat in my bathrobe in my house in Ipswich and said whatever came to mind.

This endless slow-motion fiasco began with Dan MacAlpine. He only asked for 500 words at a time, and only once a month; but it all got out of hand. It takes me 500 words just to clear my throat. And after my lifetime in big cities like Chicago and Phoenix, I found life in Ipswich so entertaining, “The Outsidah” could have been daily. Maybe hourly. Sue me; I’m loquacious.

When the Ipswich Chronicle  merged with two other papers to become the Chronicle & Transcript, one unintended side-effect was that now, six towns instead of just one were subjected to the Outsidah’s nonsense. This gave me a vast swath of the North Shore to comment on, which was almost certainly a mistake. Instead of only a few thousand Ipswich residents squirming as, for example, I considered the Ipswich train station and proffered a proposal on porta-potty potential — which I still say is a grand idea — now there were housewives in Hamilton, widows in Wenham, and various readers in Boxford, Topsfield, and Middleton, all at risk of being rankled, or simply bewildered, by the Outsidah’s odd opinions.

Anyway, for me, it’s been a hoot.

For my readers, eh, maybe not so much.

My wife Kristina — who is an honors student in Literature at the University of Massachusetts, so she should know — observes that my 300 columns have really been just four columns ceaselessly regurgitated. There’s (1) the column about local traffic, (2) the column about local weather, (3) the column about local wildlife, and (4) the column reflecting what former Ipswich town manager Robin Crosbie called my “morbid fascination with local government.”

I don’t prefer to think of The Outsidah in such irksome terms. I would say The Outsidah has been 300 brilliantly variegated essays which have just happened to clump around four utterly captivating themes. With varying results.

For example, in these 300 columns:

  • I have interviewed a cigarette-smoking deer, a mosquito on vacation, and a grieving chipmunk widow, and eavesdropped on a squirrel-couple’s domestic dispute.
  • I’ve insulted both Rowley and Saugus so often, it’s become a contest, with prizes, and a parade.
  • I’ve been flamed (more than once) for my wisdom about right-of-way on North Shore thoroughfares.
  • I’ve publicly accused a Town Manager of stealing my garbage can. (Charges later dropped.)
  • I’ve offered major public-service reporting, like my exposé on feral chickens.

And so on. You can see how I’ve contributed to the quality of life around here, right?

It feels strange, in a way, to have 300 columns behind me. “The Outsidah” has outlasted the Little Neck controversy (during which I patiently taught non-local readers how to pronounce “Foeffees”), the perchlorate crisis (also featuring a pronunciation lesson), the endless “almost finished” construction of Ipswich’s High Street bridge (which was good for, I don’t know, three or four dozen columns), and the appearance of a bear in someone’s backyard. I’ve commented on and survived countless nor’easters, potholes, and lawn-watering bans — and weathered multiple local elections and Town Meetings — all, I’m happy to say, without losing more than a couple hundred friends. The Outsidah has had something to say about New Hampshire drivers, cell phones in church, the vending machine at Ipswich Town Hall, and dog poop.

Where else could you get all this valuable stuff?

Yes, I know, it’s been mostly silliness. There are far more important things in life than whether Topsfield wins the Chowderfest competition. So I’m going to try to have it both ways: celebrating 300 “Outsidah” columns AND doing something meaningful.

Here’s the plan:

I’m going to release a new book, Ipswich in Stitches: The Outsidah’s Greatest Hits So Far. Illustrated as always by lame cartoons, this book will feature — if not the funniest columns, then at least the least lackluster columns, of the first 300.

To launch the new book, I’ll throw a party at Personal Best Training Studio, high atop the Ipswich Ale Brewery at 2 Brewery Place in Ipswich, beginning at 7 p.m. on Wednesday, March 25th. You’re invited.

The new book won’t be off the press by then. But to pre-order an autographed copy of Ipswich in Stitches that evening, you can make a $30 tax-deductible contribution to, the humanitarian charity I lead in the former USSR. See how we’re turning this into something meaningful?

Anyone who donates $30 or more between now and March 25th can also receive an autographed copy on request — and if you’re an Ipswich resident, I’ll be happy to deliver your copy in person.

Questions, comments, complaints, hate mail, and/or snarky rejoinders will be happily received; just email Also feel free to send up to 7,200 ideas for new columns.

Okay, NOW you can stop reading. I’m done for the day.


Yes, Doug Brendel really does write in his bathrobe. Good luck trying to un-see that now. Follow Doug’s ongoing nonsense here at, or his less nonsensical stuff at


3 thoughts on “Then There Was the One About Greenheads Dating

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