Hi and welcome !!
That mistake with the Abyss is very common with the same results at the end and that’s why I don’t even get close to them!!
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It always amazes me that when listening I think to myself “how can it get better than this” and then something comes along and blows what I have away.
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Don’t know about the first “wow” honestly but my first “Love at first listen” were the Audeze LCD-3… the sound signature just made me want to sit back, relax grab a Scotch and a nice cigar and enjoy life (and I don’t smoke or drink really 
).
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And that’s what it’s all about. Forget all about the gear and enjoy the music… 
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Whiskey (rum) and music, with a good audio chain are what it is all about!
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funny you named the LCD 3!
The only Audeze I kinda liked
Seems no one understands it, when I mentioned it elswhere.
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I started in the stereo world, and so my standards for “wow” were set there. I’ve had a few great headphone experiences (original Sennheiser Orpheus, HD650, HD800, Focal Stelia) but nothing has made an impression on me like a pair of Apogee Caliper Signature ribbon speakers with massive Krell monoblocks and a Wadia front-end managed in the early 1990s.
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Amen.
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Amen to that
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As long as I was there auditioning Focal’s Elear, which sounded great, I listened to the Utopia. Couldn’t tell much of a difference.
Tonally, Elear have an elevated upper mid-range, a significantly depressed lower-treble and presence region and lack air and space compared to the Utopia.
They sound, and measure, quite differently.
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Koss porta pros and then VE Monks. Crap, it used to be so cheap, used HD650’s led to various others that I let go, then Verite and Verum One, I am done now, yep, unless some raal’s and Jotunheim fall into my lap.
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I still enjoy my PortaPros daily.
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Shure SE846 IEMs were my first pair of “high-end” back then and made me realize how mediocre my experience has been listening to my then favorite Apple Ear pods. Fast forward a few years and the Stax L700+D50 Energizer was just an out of this world experience which unfortunately didn’t last long because I acquired its big brother, the SR-009S and the Focal Utopia. Time went by and the SR1a was released and oh boy, talk about another level of performance and aligned with my “end game” goal - the SR1a has set the bar outrageously high for another set of headphones to WOW me.
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I still have my SE846 for nostalgia and still listen to them from time to time.
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My humble Sony MDR-V6. First pair of “upgrade” headphones I purchased many years ago. I vividly remember listening to Fun - Some Nights and couldn’t believe the energetic sonic bliss and resulting dopamine rush I was experiencing. Instantly hooked.
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Focal Clears. Currently own Abyss Diana V2.
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The Ultimate Ears Triple.Fi 10s - blind purchase. Used them for almost a decade before they broke and never felt the slightest urge to upgrade.
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My first ‘audiophile’ headphone was the hd650. I ran it through a little setup from Headroom. Some here might know of it.
I appreciated the sound as a marked improvement over anything else that was popular for non-audiophile consumers of the time.
BUT… My first real holy crap moment was the ZMF Vibro. I loved the look of the wood cups, and figured I’d give them a shot. They had everything I didn’t really get with the hd650. They made music magical for the first time. Since then, Zach hasn’t been able to get rid of me.
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