As a twenty something, I had a boss that wore a Rolex Day Date, and he teased me about my Seiko ani-digi relentlessly, so, I purchased a Day Date, yellow gold, pre loved and at a great price from the largest Rolex AD in Boston that happened to be in the same building as a HiFi store I managed in Harvard Square.
I had a deal with the owner of that shop, Alpha Omega Jewelers, and he would provide me actual cost on his goods and I did the same for him as he was a HiFi junkie. I even bought my wife's engagement ring from him.
I did not like the yellow gold, it was a bit much for me at age 23, so, I had him look out for a white gold version of that same watch, and about 6 months later, he came through and I traded in the yellow for an almost even trade - I gave him a tiny bit of cash as back then, the WG versions were hard to even give away, seemingly.
A year or so later, I purchased a Sub from him, and I still had both watches when I joined the "other place" over 10 years ago, after I got into the TV watch craze with Invicta and others. That TV thing got me to find the other place, and I quickly began dumping all of my TV watches and started to look for other, new friend recommended watches.
The two Rolex watches were sold not too long afterward as I have always had a somewhat adverse reaction to advertising wealth and they sat in my drawer, one of the reasons I went from a BMW 5 series to a VW Jetta, although, as you know, my Jetta appears somewhat stock, but is anything but as I love performance.
So, mostly giving away the TV watches as none were too expensive and selling the two Rolex, I started looking for my first "better" watch and needed it to be somewhat of a bargain as my knowledge was not what it is today, so, I looked for a brand that had cred, but I could purchase for short money.
I purchased this from Bernard Watch for $999. Not an in house caliber, but I really liked it.


I paused for a while, still getting rid of my TV watches, I had purchased quite a few, and then, I went a bit nuts with getting an Ebel BTR and some other "darlings" of the old place, I even went to meet many of them in Florida on two occasions and went watch shopping.
That is about the time, in my modern interest period, that I purchased my first, to me, luxury watch; the GO Panomatic Lunar.
Lots of changes, trades and purchases since then, but that is the way it started for me.
What's your beginning watch story? Looking forward to seeing your responses!