Teething Sleep Regression: How Molar Teething Turned Nights Upside Down

If you had asked me a few months ago about teething, I would’ve rolled my eyes and said, “Oh yeah, it’s rough… but we survived the first six teeth, so we’re basically veterans now.” Little did I know that the first six teeth were just the warm-up act. The teaser trailer. The introductory chapter titled “You Have No Idea What’s Coming.”

Because now we’re in molar season. And molar teething sleep regression is no joke.

We saw the swelling in his gums for a full week and a half before anything actually surfaced. Just these big puffy areas that looked like they were plotting something against us. Then—surprise!—his bottom lateral incisor popped through first like it RSVP’d incorrectly and showed up a day before the molar. The molar eventually made the tiniest appearance after all of that swelling and honestly, I expected more fanfare after two weeks of sleep deprivation.

Which brings me to the real storyline: sleep has left the chat.

We’re talking almost two weeks with no signs of stopping with hardly any sleep, endless bedtime negotiations, nightly parties between 1–3am that none of us asked for, and being forced to reincorporate night feeds.

And I cannot stand giving Tylenol or ibuprofen. The actual physical discomfort of my child in pain is one thing, but the mental discomfort of trying to navigate the CDC changing recommendations around NSAIDs is another. Every time I reach for that medicine syringe I feel like I’m entering a courtroom.

Before bed we try to do the “natural” comfort things: frozen fruit popsicles, jaw massages, cold teethers. All of which work… for about four minutes. Eventually we cave and give Tylenol or ibuprofen if he’s truly upset, because watching him writhe in pain isn’t exactly the hill I’m trying to die on. But again: confusion, guilt, second guessing, repeat.

We are lucky in one sense: our child is very vocal about what he needs. If he wants ice, he’ll point at the freezer. If he wants medicine, he’ll point to the cabinet. If he’s thirsty, hungry, or wants milk, he will absolutely let us know. We can usually narrow it down pretty quickly before bed. But at 1 AM, in the dark, with no lights, half a brain cell, and a full workday ahead of us? The communication becomes much more… interpretive. It’s like trying to solve a puzzle at 20% battery.

We’ve also reverted to night feedings, which is a sentence I didn’t think I’d be writing at this stage. It calms him, it settles him, it gets us all back to sleep. Except then I’m lying awake afterward worrying his teeth are going to rot out of his skull. This is the glamorous side of motherhood nobody puts on social media.

There are moments during all of this where I genuinely feel like I’m doing something wrong. Like everyone else has figured out the “scientifically correct” teething protocol and I’m just winging it at 2am with milk, Motrin, and a headlamp. But then there are random days sprinkled in where everything works, bedtime is smooth, sleep is peaceful, and I think — maybe we cracked the code! Except it only works for that one day and never again.

Meanwhile, I already know we’ve got one more incisor and three more molars headed our way over the next few weeks and all I can think is: please just come in quickly so my poor baby can stop hurting.

We’ve stuck to our bedtime routine, but lately he’s decided he needs Dad physically present in the room to fall asleep. Not for comfort — purely for sport and procrastination. Dad is essentially the world’s most exciting sleep deterrent. We’re trying to stay consistent so we don’t build new habits we regret (looking at you, night feeds), but when your child is legitimately in pain, consistency feels theoretical at best.

Honestly I just wish teeth weren’t such a dramatic milestone. They’re vital for survival and nutrition — yes — but did they really have to enter the world like medieval torture devices? Couldn’t they just appear like nails or eyebrows? Babies would be so much happier and I would be so much less caffeinated.

To all the parents currently in teething season: solidarity. And may the molars come in quickly and the sleep return swiftly.

With Love, Mommy & B 🩵