Open Enrollment Live Blog: Hour Three and the Dentist Is Still in the Wind

It's the second Tuesday of November, which means roughly 150 million Americans have opened a browser tab titled "2025 Benefits Enrollment Portal" and immediately felt their souls leave through the nose. We poured one out, put on our sour face, and live-blogged the entire experience so future historians can understand how a superpower chose its own dental coverage.

All times approximate, because time is also a benefit that requires a premium tier.

9:02 AM — Login Screen

The portal wants my employee ID, the last four digits of my Social, my mother's maiden name, and — inexplicably — my favorite candy from a dropdown menu. I select "Twix." I don't even like Twix. The portal knows this. The portal has always known this.

Password rejected. Contains a dictionary word. Fair. I try "Gr1eF2025!" Rejected: cannot contain the word "grief." Okay, sure, that tracks.

9:14 AM — The Greeting

"Welcome, Valued Employee! Open enrollment is your once-a-year opportunity to choose the coverage that's right for YOU!"

Right for me. That's cute. The options are: (a) a plan that covers everything and costs more than my rent, (b) a plan that covers nothing and costs slightly less than my rent, and (c) the PPO, which is just (a) and (b) holding hands in a trench coat.

9:31 AM — The Jargon Translator Fires Up

Before we go further, a public service. Here is what HR language actually means:

• "Competitive total rewards package" — You get insurance. Legally. Congratulations.
• "Employee contribution" — The amount your paycheck bleeds before you even see it, like a vampire with a 401(k).
• "Network flexibility" — Some doctors will take this card. Not your doctor. Some doctors.
• "Wellness incentive" — Walk 10,000 steps a day so the company saves money and you earn a $12 gift card to a smoothie place that closed in 2021.
• "Ask your provider if this plan is right for you" — Your provider hung up.

9:47 AM — Power Rankings: The Worst Plans, Ranked

Every enrollment season, the portal rolls out a fresh lineup of options with cheerful names that sound like video game DLC. Our official rankings:

5. The "Bronze Adventure Pass" — $6,000 deductible. Covers nothing until you've personally financed a small wing of the hospital. Ideal for people who plan to be perfectly healthy all year and also want to pay $340 a month for the privilege of not using it.

4. The HSA "Triple Tax Advantage" Plan — Yes, triple. Tax-advantaged. Advantageous to whom? Follow-up question not permitted.

3. The "Silver Choice Network" — Includes your primary care physician, who retired in September. Includes the new one, who is two states away. Includes, technically, a naturopath in Reno.

2. The Dental Plan — Covers 50% of fillings, 0% of the crown you actually need, and requires a waiting period longer than the average engagement. My teeth have been "pending eligibility" since March.

1. The Vision Plan — $11 a paycheck. Covers an eye exam at two participating locations, one of which is inside a former RadioShack. Does not cover lenses, frames, contacts, or, judging by the fine print, eyes. Still, I enroll every year. We all do. It's $11. It's the cheapest way to feel insured in America, and honestly, that feeling is the real benefit.

10:15 AM — The Life Insurance Math Section

The portal helpfully suggests I need life insurance equal to eight times my salary. I do the math. I do it again. I open a calculator app. I close the calculator app. Some numbers are not meant to be seen.

10:40 AM — The FSA Gamble

Flexible Spending Account: guess how much medical care you'll need next year, and if you're wrong, you forfeit it. It's fantasy football, except the prize is orthodontics and the punishment is losing real money. I put in $600, which is either too much or catastrophically little. There is no correct answer. There has never been a correct answer.

11:03 AM — The Deadline Pressure

A red banner appears: "You have 14 days left to enroll. After that, you'll be locked out!"

Locked out of what, though? I scroll back up. The Bronze Adventure Pass has a deductible of $6,000. If I get locked out, I'll just... not have insurance, which is what the insurance was protecting me from anyway. The system has achieved perfect circularity. Somewhere, an actuary weeps with joy.

11:22 AM — The Confirmation Screen

"Thank you for enrolling! Your elections are confirmed. Coverage begins January 1."

A green checkmark. A little confetti animation. Eleven months from now, I'll do this again, slightly older, slightly more deductible, slightly deader, and the vision plan will still cost $11 a paycheck, and I will still buy it, because at some point it stopped being insurance and became a friendship.

Final Whistle

Open enrollment is the one time of year America admits it doesn't have a healthcare system so much as a slot machine with a dress code. You pull the lever, the HR jargon rains down, and whatever lands, you keep until next November.

Pour one out for your teeth. They were never going to be covered anyway.