I'm basically a one guitar guy. I own (and have only ever owned) three electric guitars. I started on acoustic when I was fourteen, so it was a couple years anyway before I even wanted an electric. I had tried people's electrics (Strats and Les Pauls) but they weren't really my cup o' tea. The summer after my sophomore year in high school, I tried a friend's electric, and for the first time, I loved the way it felt. It didn't play like any of the electrics I'd tried up until that point. I was like 'hmmm, so this is great. When I do get an electric guitar, it will be whatever type this is. Incidentally, when I asked him what type of guitar it was, he told me a brand name I hadn't heard of before... it was a Paul Reed Smith. (This was in '94... I was 16.) After proving to my parents that I was sticking with the instrument, they agreed to letting me get an electric guitar for the holidays.
We went to Daddy's Junky Music in Boston, and we asked the salesperson if they had any Paul Reed Smith guitars. So he takes us to the back room, and starts showing me Customs which start at like $2500. My (and my parents') eyes nearly fell out of our heads. None of us had any idea how much the guitar was going to be; I think we all assumed it would be like $400-500. The salesperson, sensing the discomfort, instead showed me one of the CE24 models, which he told us was the same quality as the Customs, but you don't have to pay for any special options like a 10-top, birds, etc., and that we'd not be paying any extra labor cost that goes into the gluing process of a set-necked guitar since this one had a maple neck. I promised to pay for a portion of the guitar, my parents conceded, and got the PRS.
I'm still playing this PRS today, 30 years later. I loved my guitar so much so that I wanted to work for the company (and eventually I did.) While working there, I got my second electric guitar: a modded version of a Hollowbody 1 (I'd wanted a hollowbody since I'd started playing, having been obsessed with Trey Anastasio of Phish.) This time, I got to choose my own stain color, electronics, and other little things.
My third (and final) electric guitar is an Eric Johnson Strat. When I had started playing out, I played a lot of funk, and could NOT get the correct tone I wanted while playing some of the songs we were covering. Turns out I needed a single coil guitar. Similarly, I had tried someone's EJ Strat at one point and thought to myself 'if I ever had to get a Strat, this will be the type.' And so it was.
Incidentally, I still play my original PRS CE24 95% of the time, despite the customizations of the Hollowbody. The scale length, neck carve, and 24-frets are just perfect for me. (I swapped out the HFS/Vintage Bass pickups with uncovered 24/08s, which I love.) The Strat sits dormant in its case for the most part, other than an occasional recording.