This is the poorest, most evil app to ever come out of Google
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It's Google's. Android Wear is one piece of satanic work, well-suited to torture unsuspecting geeks who just want to get their smartwatch to finally, praised be the Titans, pair with their smartphone. Things aren't quite so simple with Android Wear, however. In fact, we have absolutely no qualms about calling the Android Wear platform and its homonymous app sidekick the poorest, most annoying piece of software to ever come out of Google's labs. This is all the more troubling, seeing as how smartwatches aren't doing very well anyway, and need all the help they can get. And if the train of thought below is hard to follow, it's only because we ourselves have absolutely no clue what on earth possesses Android Wear to act the way it does.
So what's wrong with with it? As touched on, pairing can be an absolute, utter nightmare because the platform obviously was only intended for one single wearable, even though it can supposedly support many. If you're about to buy an Android Wear smartwatch, don't fret — first timers are usually fine. But if you're thinking of pairing up a new smartwatch whilst keeping your smartphone, or unpairing your smartwatch to temporarily connect to another smartphone, or even if you have two wearables and like switching between them, be prepared for one hellish ride.

Hopeful as it looks, you'll never get past the 'Connecting' stage.

Half an hour and one factory reset later, still no luck
Since sync loops are the most deceptive, they're worth further clarification. They occur when the smartphone tries to transfer all relevant data to the smartwatch during initial contact, but the phone, for some reason, runs into trouble. Last week, we waited about 45 minutes before giving up and going for another reset (then it worked). Just today, whilst prepping the Watch Urbane for our video review (it connects to a Galaxy S6, which had previously paired with the Urbane, but tried to switch (unsuccessfully) to our resident Watch R), we ran through the same scenario. After resetting it, we managed to pair it with the S6 and "only" had to wait 20 minutes for the syncing process to finish. What can possibly require so much time? Certainly not the 10 to 15 third-party watchfaces or the handful of apps we've installed. Even through Bluetooth, this is way too long.
We get it, smartwatches are a new category, but after two years, the latest Android Wear version shouldn't be marred by such glaring issues. It's not alright when a new update or the thought of pairing up our resident smartwatches with a new device fills us with dread — we don't need it to be 100% plug-and-play, but Google should absolutely look into this if it's at all serious about the category.
Things that are NOT allowed: