Back in the late aughts, someone down the hall from my office shut a metal door, and in my head, it made more noise than it should have. Something was wrong with my ears, and after a month of bouncing between doctors, an audiologist told me I'd lost about half the hearing in my right ear and picked up a bit of tinnitus to boot.

Thanks to the nature of the destruction caused by the nerve-eating virus I had contracted, even a custom-fit hearing aid didn't help. A lot of things I still hear just fine, and people often don't pick up that I'm half deaf on one side. Thankfully, and kind of amazingly, when I have headphones on, the music still sounds like it's coming straight down the pike—I don't even notice anything is missing until some Pink Floyd-style stereo effects kick in.

Noisy spaces, however, especially where sound bounces around a lot, can be a challenge. I'll ask to sit at one of the corners of a table to keep everyone I'm with in front of and to the left of me. To engage, I have to pay extra attention, staring right at each speaker. It's usually fine, but in a loud enough space it can be exhausting.

As a result, I was excited to hear about the Conversation Boost feature built into Apple's $250 AirPods Pro headphones, which uses computational smarts and a directional microphone to help you “hear more clearly by focusing the sound on the person directly in front of you,” as the company claims.

I called a pair in as soon as I heard about them, but thanks to the Omicron surge, there was a lot of waiting for good opportunities to be around other people to put them to the test. As a result, the AirPods Pro became my daily drivers for months, largely bumping out both my well-loved Jabra Elite Active 75t in-ears, which I used for running, walking, and phone calls, and my over-the-ear Bose QC 35 noise cancelers, which got the nod for in-house and long-flight listening.

Before launching into thoughts on Conversation Boost, I'll take advantage of having had these longer than anticipated for some more general long-term testing notes. While they certainly have flaws, these are pretty outstanding headphones. Playing downloaded tunes on my iPhone's Apple Music app, they sound crisp and clear, deep and layered, rewarding my full attention and occasionally revealing parts of my favorite songs that I'd never heard. As someone who always has music on and loves to pay attention to sound, I appreciate Apple's focus on sound quality.

Contributing to this is their surprisingly comfortable fit, which includes a built-in test to make sure you've got them snugged in right. While my Jabras can get a little uncomfortable after an hour or two, it's impressively easy to forget the Pros are in my ears. Their Bluetooth range is impressive, staying connected as I wandered through dead zones for other devices.

On the other hand, having the AirPods connected to both my recent-model iPhone and MacBook could be a surprising pain in the butt. Mostly, I use headphones connected to the phone, not the computer, but the computer always wanted to grab or announce its willingness to share the connection when I didn't want it to, like when I'd just dialed someone's phone number. Rather nuttily, putting the headphones on might wake the sleeping computer from across the room even though I had the phone in my hand and was heading out for a walk. Once, on a plane to Chicago, I popped open the case and watched their icon pop up on the iPad screen of some dude across the aisle, where it said something weird like “Not Your AirPods.”

Yes, Bluetooth can be frustrating on all kinds of gadgets, but as is, the inter-Apple ecosystem pairing oughta be better than this. It all made me pine for a device with a dial—like an old-school kitchen timer—where I could physically set what I wanted them to connect to: my phone, the computer, or both. I'd like to think this is all fixable with firmware updates, but I’m not terribly optimistic in the short to medium term. (In the final editing stage of this story, I was sitting at the computer trying to listen to the KEXP app on my iPhone, and in the space of 10 minutes, my computer stole or tried to grab the connection more than a dozen annoying times.)

Sticking with airplanes for a bit, I appreciated the noise canceling, which was quite good for in-ear headphones, but it understandably couldn't pierce the lovely privacy bubble my Bose over-the-ears create (or their bigger, more enveloping sound when watching movies).

I also found the on-headphone controls a little clunky and inflexible. It might just be what I'm used to, but I really missed on-ear volume control. If that's firmware-fixable (hint, hint), I'd happily sacrifice on-ear listening mode (noise canceling/normal/transparency) for volume.

Following the suggestions of the folks at Apple, I turned on Conversation Boost in Transparency mode (similar to the hear-through mode on my Jabras and other earphones on the market) and adjusted other settings like Ambient Noise Reduction and Amplification. Then I headed to dinner with some friends at Seattle's busy new restaurant, Jackalope. (Tip: The short-rib fajitas are worth the splurge.) Sitting down at our table of five, I told everyone what I was doing—wearing headphones to help hear them, not ignore them. Then I put them on and tried to embrace the idea that I sat down to dinner looking like I had golf tees hanging out of my ears, à la Parker Hall's original review, and joined the conversation.

Considering I had headphones in my ears, which would usually block sound from coming in, the performance was impressive. I could hear the woman sitting at the far corner of our table fairly well. The noise of the restaurant became a weird sort of white noise, like I was listening to it just under the surface of a lake during a rainstorm. Three things immediately struck me. First, Conversation Boost clearly worked, but it wasn't a decisive improvement over not using the headphones at all; the feature was a little more interesting than out-and-out helpful. Second, even having explained what I was doing, I still felt weird wearing headphones at the dinner table, uncomfortable with the message it sent, especially when I tried to fine-tune the settings on my phone while the conversation went on around me. Third, I was really glad Apple is experimenting here, even though Conversation Boost has a beta-stage feeling to it.

Here's an example of that last point: You control some features on the AirPods themselves, some in the volume settings in Control Center, and the nitty-gritty details in the Hearing section of Control Center. Having them more neatly consolidated somewhere would make the feature easier to use. Some presets like “loud restaurant” or “multiple conversations around me” would be nice starting points.

Not long after that dinner, Omicron turned me back into a homebody, which meant one of the only places I had regular contact with people where Conversation Boost would be helpful was at the grocery store. If I had Transparency mode on, which it needs to be to use Conversation Boost, it gave the whole store, with its air vents, chatting customers, and stocking clerks, that underwater-in-the-rain feeling. Communicating at checkout was a lot like it was at Jackalope, and I could never figure out if I should tell people I was talking to for 30 seconds that I was using my headphones to help me hear them. Over the course of a few months of this, I gently circled in on a feeling with them, and a lot of it focused not on how the AirPods Pro performed, but how they were perceived, and how they make people feel.

When you're out in the world, headphones can signal all sorts of things, such as “I'm grooving to my music” or “Buzz off!” Both are great in their own way. They definitely don't say, “Let's communicate!” Some days, I'd leave them on and chat with the cashier to learn more about how the Conversation Boost feature performs, but I always felt weird about it. One day when I didn't have the Pros with me and was having a funny chat with a twentysomething cashier-bagger comedy duo, I asked how they felt about people wearing headphones while talking to them.

“It takes 30 seconds to check out,” said the cashier, who was understanding but not a fan. “Just be present.”

The bagger had sharper words.

“There's something in our upbringing that tells us you shouldn't do that.”

That crystallized what I already knew, and I haven't put them on since for casual encounters.

I loved having the opportunity to listen to the AirPods Pros for an extended period of time. I did not love their Bluetooth eccentricities and really hoped for more there. As someone with hearing issues, I found Conversation Boost to be a mixed bag, but I was just happy Apple's engineers are thinking about this, and I have the feeling the feature will improve over time. I bet they'll be able to refine the boosting, shutting out more of the external noise and honing in on the people in your group. I hope they find a way around the ”talking to someone with headphones in” problem. Maybe instead of tech companies putting creepy cameras into smart glasses, they could design truly excellent directional microphones.

When Omicron ebbed in April, my wife, Elisabeth, and I went to a restaurant with some old friends. Having prepped them ahead of time, I put in the AirPods. I could hear Kristin pretty well and Greg, who was closer to me, a little less so. Perhaps it had something to do with the tone of their voices. It didn't seem to hurt, but it didn't help a lot either. After a couple of minutes, I got self-conscious and stuck the headphones back in my pocket. I didn't want to fiddle around with the settings, I wanted to be present.