The worst email subject line I've ever seen

...and even given that, it's so much worse

Jun 24, 2026

Hello Gobbledeers,

How’s it going?

Has this ever happened to you?

You have a weekly newsletter that you write. You set aside time each week to write it, which is important because you publish the newsletter every Wednesday. You get more than half of it done, but figure you’ll finish the rest of it up on the plane. Then you fly United, and the plane’s wifi has a speed equivalent to the speed at which my Atari 800 used to use a 300 baud modem to connect to a local BBS. Yes, that is a very nerdy reference from 1982. The speed of the wifi makes it impossible to write the rest of the newsletter. So you have 2 options:

Option 1: Send a Gobbledy Classic (tm). Pro: Newsletter goes out. Con: some people have already read it. Also, feels like cheating.

Option 2: Send what you’ve written. Pro: Newsletter with new content goes out. Con: It’s not finished.

I figure it’s better to loved and lost then never to have loved at all. Or something. That means you’re getting Option 2. Just know that there was going to be some delightfully humorous stuff about Polymarket, though whatever you’re imagining is definitely better than what I had planned.

Thanks for continuing to tolerate my occasional lapses.

This week we’ve got:

Hotel signage
The worst email subject line
The Gobbledy AI Correlary (tm)

Oh, and we’re off for the holiday next week. Happy July 4th!

Share Gobbledy

And also free breakfast…

Sometimes I’m just stumped, too…

If you’re a hotel manager, and people keep breaking into the cars of the guests at your hotel, you’re going to need to tell the guests about this unfortunate situation.

And sure, you could just whisper it to them at checkin - “Shhhh, let’s just keep this between us, but you may - may! - want to make sure your car is locked because - and I don’t want to alarm you, or any other of our guests - we’ve had a few car break-ins recently, and while I’d prefer if that didn’t happen, I wanted to make sure you knew. Also breakfast is 630-930am right here in the lobby, except on Saturdays when it’s 7-10 and on Sundays when it’s 730-1030, except this Sunday when it’s Easter brunch at 9:15.”

But that’s a lot of information to convey to someone when they just want to go to their room. So it’s probably best to just write something up letting people know about the break-ins and then stick it in the elevator.

Which is what reader Joe S. found at his hotel in Philadelphia. He and I both appreciated that the manager of the Four Points remained chipper even after sharing the bad news:

Your car will get broken into. Enjoy your stay!

(I mean, what else are you going to write? “You should stay somewhere else?”)

Smoke Gets In AIs

A quick thing:

I was texting with a friend and we had a stupid idea about something related to smoking, and I looked up “smoke.ai” because of the Gobbledy AI Correlary: If there is a word, then there is an AI company named for it. And of course there is a “smoke.ai” that is some sort of sales and marketing something something.

I’m mentioning it because there are roughly 11 million of these AI sales and marketing something something companies all trying to figure out what to say on their website about what they do for you, and they can’t all say “we let you send an ungodly fuckton of emails to people who don’t want to receive emails from you.” But I did like this as a message:

Nice, no?

(And I haven’t seen “out of the box” in a while. And also I’m now so old that people starting companies never actually saw software in a box.)

A Croc of Shit…

Every so often I mention that early in my career I was involved in email marketing, and mostly what I remember from those days is the paralyzing fear of spelling something incorrectly in the email, and the dread of pushing the “send” button, knowing that you will find that “something incorrectly” 3 seconds after you hit send.

But the other paralyzing bit about working in the email marketing racket is that you have to come up with an absurd number of subject lines. Sure, this is much easier to do this nowadays than it was in the pre-AI period.

Sorry - I mean that it is now easy to come up with lots of not-particularly-interesting ways to say that the sweaters are 40% off. (If forget if I ever mentioned here that back in my Hilfiger days I tried to fight the monotony of “Sweaters are 40% off” subject lines by suggesting we write “Sweaters are 60% on,” which, I was told, was not “on brand,” as apparently (?) the brand guidelines only allow you to speak of sales in terms of “off” and not “on,” except if something is “on sale.” Wow, brand guidelines are difficult. The Hilfiger brand team really had a thing for prepositions. Or about prepositions. (preposition humor!)

(I’m always amazed that that machine continues chugging along to this day):

(Milled.com is an excellent resource for looking up retailer emails, btw.)

So given those limits you've really got to dig deep to keep those subject line creative juices flowing.

And one place to dig is referencing current events in a clever way.

Maybe if your company is having a promotion for Pride Month, you could go with (and I’m sorry) “The Strait May Be Closed, But The Gay Is Now Open!”

(Did I wrestle with keeping that in here? I did. Did I lose that wrestling match? I did. Is it a good rule of thumb that if you’re ever “wrestling with” whether to include something you’ve written in a newsletter, that you should not include it in the newsletter? Yes it is.)

As you can see there, referencing current events can be a hit-or-miss strategy.

Like, for example, if you work for Australian Groupon-esque company Wowcher, you’re probably pumping out deal emails constantly. And those deal emails are going to need subject lines. And those subject lines are going to need to be written by someone. And that someone is you.

And you may have just read the actually horrible story about how a lunatic tossed a young child (he survived!) into a crocodile enclosure at an Australian zoo. Which made you think, for some reason, that that could, perhaps, be the foundation of an eye-grabbing subject line.

But it’s not! Do. Not. Use. This. As. A. Subject. Line.

Oops, too late: