“Cuffing Season” Is a Cynical Name for Something I Actually Believe In

I want to talk about a word I don’t like, and then about why I’ve spent thirteen years building the thing it’s making fun of.

The word is “cuffing.” As in cuffing season, as in handcuffs, as in: you have been apprehended. Somebody’s got you now. You’ll be released in the spring with time served.

It’s a funny word. I get why it caught on. But every time I see it I notice the same thing — it’s a joke that lets everybody off the hook. If the whole enterprise is a bit, if wanting company in November is just a seasonal punchline, then nobody has to admit they want it. That’s the actual function of the word. It’s not a description. It’s cover.

The cynicism is a defense mechanism, and I say that with affection

Look, I taught high school English. I spent years in a room with teenagers, which is a very good place to learn how people talk about things they’re scared of. Nobody makes fun of something they don’t care about. Indifference is silent. Sarcasm is loud, and loud means invested.

So when I see someone post “lol cuffing season is upon us, time to acquire a winter boyfriend,” I don’t read a cynic. I read somebody who wants a person and has learned that saying so plainly is the riskiest sentence in the English language. So they say it in a costume. The costume is the joke.

Which is fine, honestly. People are allowed their armor. I just think it’s worth occasionally taking the armor off long enough to notice what’s underneath, because what’s underneath is not embarrassing at all. It’s this: the days get short and I would like somebody to be indoors with. That’s it. That’s the whole confession. Humans have wanted that for as long as there have been winters. It’s not a bit. It’s one of the oldest true things about us.

February 2013

Here’s why I take this personally.

LFGdating started with a phone call. Patrick called me from Hawaii — he was a Marine, stationed out there, and I was in Georgia teaching, which put about 4,200 miles between us. It was late. It was a Tuesday. He said, “You said you could make a dating site for gamers, right?” I said yeah, I’ll need your help, but yes. He said, “Alright — we’re doing it then.”

I will never forget that phone call.

Then we built it, which took two years of nights. I’d get home from school around 4:30, eat, grade papers until seven, and then go into LFGdating mode until eleven or midnight. Pat was up at 4:45 every morning to do his half before his actual job. We opened the beta in January 2012 and closed it in February 2013, which is when the site officially launched.

And here’s the part I think about every single fall.

The day our first real member ever signed up, I was on an elliptical at the gym. Last day of semester finals. My phone buzzed: “Congratulations! You have successfully created a profile on LFGdating!” And my first thought was, wait, I didn’t create a profile — oh. Somebody else did. I about fell off the machine.

Then the school intercom announced we were closing immediately for a blizzard. I drove home through it, made a pot of coffee, and got back to work.

So the founding memory of this company — the actual origin moment, the one I’ve told a hundred times — is a stranger deciding, in the dead of winter, in a blizzard, that they’d like to find somebody. February. Peak so-called cuffing season. The middle of the exact window the internet has decided to be sarcastic about.

I’ve never once thought that person was doing something funny.

The bottom line that isn’t financial

We say publicly that LFGdating has two bottom lines. The first is how many people are meeting and communicating on a daily basis. The second one is the money.

That’s not a mission-statement flourish, it’s an operating reality, and here’s the tell: when a paying subscriber cancels because they met somebody, that email is the best thing that happens to us all week. A customer leaving is the win condition. I’ve described it before as basically every great holiday wrapped up into one notification, and I stand by it, even though it makes no sense on a spreadsheet.

Which is why the cuffing framing bugs me at a business level too, not just a sentimental one. That framing says the goal is acquisition — get a person, hold a person, release the person when conditions improve. It treats a human being like an item you equip for a debuff.

Everything we’ve built is pointed the other way. We’re not trying to help you acquire somebody for four months. We’re trying to put you across a table from a person who already speaks your language, so you can find out if there’s something there — and if there is, we would genuinely love to lose your subscription over it.

What I’d actually say to you in October

If you came to me in October and said you were feeling the pull — that the evenings got long, that the group chat isn’t cutting it, that you’d like somebody — I wouldn’t make a joke about it. I’d say four things.

One: wanting company is not weakness, and the season doesn’t make it fake. The timing of a want doesn’t invalidate the want. Nobody says “well, you only got hungry because it was noon.”

Two: say what you’re looking for. Out loud, in words, to the actual person. Most of the wreckage attributed to this season isn’t seasonal at all — it’s two people who never told each other anything and then acted surprised. That’s not a cuffing problem. That’s a Tuesday problem that happened to occur in December.

Three: don’t make a person your treatment plan. If the fall lands heavy on you every year in a way that doesn’t lift, please talk to somebody qualified about that. Date too if you want. Just don’t hand that job to someone you met three weeks ago — they’ll fail at it, and it won’t be their fault.

Four: start now, not in November. This is the practical one and it’s the one people ignore. Everybody has the same idea at the same time, and the people who do well in this season are the ones who set it up before they urgently needed it to work.

The invitation

Thirteen years ago, Pat and I built this because we’d both spent our twenties on mainstream dating sites explaining ourselves. We wanted something neither of us had at the time — a clean, tasteful dating site for mature gamers, where being one wasn’t a disclosure you managed but the premise everybody arrived with.

That’s still the entire product. Not a trick, not an algorithm we’re mysterious about. Just: everybody here already gets it, so you can skip to the part where you find out if you like each other.

The days are about to get shorter. If you feel the thing, you’re not being basic and you’re not being a cliché. You’re being a person in the fall, which is the most well-documented condition in human history.

Come find somebody. Download the app, or make a free profile — it takes about two minutes, and I’d rather you did it in August than in a panic on Halloween. If you want the practical version of all this, Monday’s guide lays out the whole season.

And if it works, cancel on us. Please. It’s our favorite email.

Stay Classy,
Casey and Pat