Searching for Silence: My Unexpected Journey into Side-Sleeping Headphones

For as long as I can remember, I’ve been one of those people who can’t fall asleep in silence. The hum of a late-night talk show, the distant rumble of an old sitcom rerun — it’s always been part of my nighttime ritual. Even after moving in with Monica, the television remained a nightly fixture. But while I found comfort in its glow, Monica did not. I’d often wake to see her wearing an eye mask and sometimes earplugs, trying her best to drown out my sleep soundtrack.

That’s when guilt — and curiosity — set in. I didn’t want my need for background noise to disturb her rest, so I began a quest in early 2023: to find the perfect headphones for side-sleeping.

Chapter One: Wired Woes

Being a fan of Creative Labs, I naturally hoped one of their headsets would work. But over-the-ear designs? Too bulky. In-ear buds? Too painful when lying sideways. So I turned to Amazon and stumbled upon my first candidate: the Hearprotek Bluetooth 5.2 neckband headphones. They were affordable at $29.99 and boasted excellent battery life. But after a few nights, I found myself battling the cord — tugging it out accidentally or slowly wearing it down to the point of a short.

Next came the MAXROCK Bluetooth 4.1 model. Slightly cheaper at $16.89 and, surprisingly, more comfortable. Despite the lower specs, I preferred them — at least until they too succumbed to the dreaded one-earbud death.

Chapter Two: A Flicker of Hope

In late September 2023, I stepped it up with the Avantree Repose. Priced at $34.99 (minus a $7 coupon), they outlasted the others — nearly six months before the inevitable short. Their buttons, like the previous ones, were inconsistent in layout and logic, making late-night volume adjustments an exercise in muscle memory.

Chapter Three: True Wireless Awakening

By March 2024, I pivoted to true wireless stereo (TWS) earbuds — specifically the Hulaed/Q26. At $29.59 (after coupon), these were a game-changer. Lightweight, comfortable, and modular: I could wear one bud while charging the other and alternate through the night.

Battery life, though, was their Achilles’ heel. One side degraded faster — likely because I favored it — and the ear tips lost their shape over time, making a perfect fit harder to achieve. But they were still my favorites… until I got curious again.

Chapter Four: Enter the S29

In April 2025, I noticed a surge in TWS sleep headphone options. Prices ranged wildly — some above $100 — which I wasn’t willing to pay. Many listings lacked clear battery life specs, an automatic red flag for me. Eventually, I settled on the Doubc S29, showing up as “S29” when pairing. They claimed Bluetooth 5.4, 8-hour usage per charge, and 53 total hours with the case. Listed at a staggering $160, they were marked down to $24.99. Amazon’s return policy gave me the confidence to try.

Nearly a month in, I’m impressed. The bass response is stronger, the fit is snug, and I love the case’s built-in charge indicators. One earbud might still outlast the other slightly — I plan to test this more closely — but for now, I’ve found a new bedtime companion.

Final Thoughts:

This probably isn’t the end of my journey with sleep headphones. Like any gear enthusiast, I’ll always have my eye on new tech. But for now, the S29s are part of my nightly routine, replacing the once-familiar glow of the television with something far more considerate — and quiet.