wow ...can't even remember my first watch.
i do agree, this thread is going kinda OT. But there could be no explanation without recalling our growing up years.
but let me recall my childhood growing up in the economic bleakness of the 80's
was luckily enough to have a father who works for one of the few Chinese banks in the era. Although money was not aplenty but the benefits was good for the family. Stayed in a 2 bedroom terrace house and father drives a simple Sunny. Never had much luxury at home. Always envious of kids having the stupid Superman t-shirts with attached capes in kindergarden and also those cool pencil boxes with tons of pop-up hidden utilities/utensils.
My brother, being the first born grandchild/grandson have everything from my grandmother. For his birthday he got a Popeye watch (the one whose time telling hands are Popeye's own big guns). Was extremely envious of him and would get beaten up whenever i sneak some wrist time with it. Mom got me a cheap plastic digital watch and somehow it was never the same.
I remember those days, waterproofing was a really big deal because nothing is waterproofed! Bloody wrecked so many digital watches by just washing my hands or being out in the rain. So went through my primary school being watchless most of the time.
But I do remember buying my first watch from ivanswk's mom when i was still in blue shorts. His mom was selling some plastic digital watches and he is her promoter in school. I remember mine being a yellow watch but wrecked it couple of days later when i was washing my hands. Was too happy with it and never took it off.
I got my first Swatch when i was in primary 5 when my grandma went to London for holiday. This was the start of the good time 90's. Money was more abundant and big time AliBaba schemes were beginning. Everyone have/had a piece of the pie and not seeing the poison that would come later.
Was thrilled with it. Kind of a big deal then but I do remember a simple Swatch was only retailing for RM80-105 in departmental stores and Chinese tea and Herbal Tea in kopitiams was only 20sen and 50sen respectively. Movies was still only RM3.50 downstairs and RM5.50 upstairs

Wore that until I got into high school until the case cracked and bought myself another Swatch from my CNY money. This time it was a leather strap and as always it only lasted another few years due to it being a daily beater. Wore that for football and everything. you could just imagine the smell of the strap.
The first cool watch I ever got was a Timex DataLink 150.
http://techland.time.com/2010/07/08/great-moments-in-geek-history-the-timex-datalink-watch/
It was the height of computer geekness and was constantly stuck infront of my 486sx playing Doom, Monkey Island, Leisure Suit Larry and etc.. downloading dirty photos from IRC

The watch is really cool, you can download telephone numbers and simple notes into your watch via the infra-red sensor on the watch face. Just point the watch infront of the computer screen and using the installed software the screen would flash a series of lines like barcodes to input the data.
Requested my mom to send the watch to me from US when she remarried and migrated there. I guess out of guilt, my mom would try to give us everything. But I lost it when I got mugged in college. Sunway and Subang was really crime infested.
Bought myself a series of Swatches again after that from ..again...CNY money. Prices went up alot from then on. Got myself the Millenium Swatch edition. Destroyed the strap when i went for swimming in the sea. The salt water just ate the glue in the strap away and buying another watch makes more economical sense. Not to mention more immediate too. Ordering the strap takes month.
[link to commercial site not allowed - Mod]
After college my only sole watch was a Swatch Irony. Took me throughout my first few years of working. With a low starting pay, after paying off rent, car, allowance to dad, petrol, insurance and etc, i was left with nothing and had to ration with just RM10 a day for economy rice. This was still when V-Power was only round RM1.50 something per litre. God only knows how the fresh grads are surviving now.
The pliers was my Swatch's best friend because that was the only thing that is keeping it from falling off my wrist. The elastic metal bracelet have a tendency to give way at the lugs. So every couple of days i have to retighten the bracelet. it's just hanging on for it's dear sad life. I was just too poor to afford another watch or get another strap without starving myself.
My first auto watch was an Orient which i bought online from lelong.com.

That was the beginning for my love for mechanical watches. Moved to Singapore, got myself a better paying job and thus bleeding ever since.
As the years goes on the watches I bought in chronological order.
Orange Monster
SKX Pepsi Diver
Seiko Sawtooth
Seiko SKA Diver - for Dad
Seiko SNA Chrono -for brother
Rolex TT Ladies DJ - for wife
PAM 112
Sinn 857s
Rolex AirKing 14000 - for wife
Rolex Sub 14060M
Wempe Pilot
Tudor Prince Chrono
Still very much modest and a long way to go... that is my story anyway

Along with collecting watches I also collect bills...