Paper Bills in 2025? The Copay That Time Forgot

Where paying the bill is harder than pulling teeth. (…and the irony is that they’ve mastered one, but not the other.)

I wasn’t planning to write about this. But when the universe drops a paper bill in 2025 with no online payment option into my mailbox, it’s basically handing me a case study in how tech fails us in the funniest ways.

I’d like to thank my dentist for keeping my teeth sparkly, my gums healthy—and my analog rage alive in 2025.

This place is beautiful. Spa-like. Scented like eucalyptus and wealth. The staff is kind, the tech is top-tier, the vibe is “if Apple designed your molar experience.” I genuinely love going.

Except for one thing.

Their payment system is stuck in a time loop. One that smells faintly of Aqua Net and shame.

“You’re all set!” (Famous last words.)

Every appointment ends the same way: I’m walked out (sorry—walked to the front and encouraged not to stop) with a smile and the reassurance that my insurance has handled everything. “You’re all set! Have a great day!”

It feels very luxe. Very VIP. Very don’t you dare stand in line like a peasant. My hygienist even books my next appointment while I’m still in the chair.

It’s efficient. It’s personal. It’s so nice.

It’s also a lie.

Two weeks later, I get a bill in the mail. A physical bill. With a perforated stub and no online payment option. And get this...not even a remittance envelope. Their website? Gorgeous. Modern. No way to pay. Just vibes and a chatbot who, when asked how to remit payment, gave me an answer that felt like it was faxed in from 1993.

So I do what any rational Gen Xer does: I dig out my checkbook like it’s 1982 and I’m paying for Girl Scout cookies. I void the first one because apparently check-writing is not like riding a bike. Second try looks like a hostage scribbled it under duress. Stamp. Envelope. Shame spiral.

I tell myself I won’t fall for the “you’re all set” routine next time.

Guess what?

I forget. Again.

The Return of the Paper Bill & Envelope

My most recent visit? Same story. Only this time, the bill arrives without perforations. I had to cut it out with scissors. I looked like a rogue crafter. Or someone assembling a ransom note in an episode of Charlie's Angels.

All that’s missing is a trench coat and a Fleetwood Mac 8-track playing softly in the background.

Naturally, I visited the vendor site on the invoice. They do have a payment portal!

…for medical practices. Not patients.

Is this some kind of Gen X endurance test? A Boomer trap? If Alan Funt walks out with a camera crew, I swear I’m billing him.

I called the office. Was put on hold. Transferred. Put on hold again. Finally heard a recording… telling me where to mail the check.

So helpful, thank you, Brenda.

If You Know, You Know

Maybe it’s generational. Maybe it’s just that weird tension between the world we live in and the one we assume we live in.

Because I can unlock things with my face. I can attend a meeting in three time zones at once. But I cannot—cannot—pay a dental copay without summoning the ghost of Office Depot Past.

If you’ve ever stood in your kitchen wondering where you last saw stamps, scissors, or your own sanity—yeah. Same.

We’ve got smart homes, smart watches, AI in our inboxes...But apparently, dental billing is where progress goes to die.

So if you've ever whispered "is this really happening?" while cutting a perforation that no longer exists—I see you. We are one awkward check away from forming a support group.

Bring snacks. I’ll bring envelopes.

If you’ve got your own analog horror story—dentist-related or otherwise—I’d love to hear it. Misery may not love company, but it definitely appreciates a few laughs.