My first carry gun was a S&W Model 14 with a 6" barrel in .38 Spl, that my granddad gave me when I was 18. I carried it for a few months, but it was mint when I got it, and wasn't going to stay that way, so it got retired in favor of a shorter, uglier S&W model 10 4" police trade, which was about all the gun I could afford on a gas station clerk's wage.
Later I downsized to a Kel-Tec P32. I hadn't yet learned the virtues of good leather, and was getting sick of being dragged down by heavy guns.
Eventually, I became concerned about the .32's lack of power, sights, and general shootability, and so went clear to the opposite end of the spectrum. I got my first 1911, a Taurus 5" .45. It had a number of issues at first, and I bought several other 1911s, including a Springer, a Rock, an old mix and match Colt, and a Sistema. They all proved to have issues of their own, however, and a much upgraded PT1911 remained center stage.
Somewhere in there, a CZ 75 and Glock 21 wandered into and out of my life. Both got carried a time or two, but not on a regular basis.
Eventually, I went through another phase of not wanting to deal with the size and weight of a 5" 1911, and started looking for alternatives. During the looking around phase, I went back to carrying the little P32. This carrying a 32 but looking for something better went on for quite some time. At one point, I borrowed my Dad's Kimber LW Faux-mmander, and thought it was an excellent compromise. It maintains most of the virtues of the 1911, but is a lot lighter, and just enough shorter not to pinch.
I was all set to pull the trigger on one of my own, when an accident at work led to my switching to shooting lefty. All of a sudden, a lightweight .45 didn't seem like quite such a great idea. I had just about decided to start looking for a G19, when I remembered how mild shooting my RIA Gov't size .38 Super had been. I also remembered having heard about LW Commanders in that caliber. I figured that even my left hand should be able to handle that.
Pretty soon, the stars aligned, Colt made a run of them, and after seeing three of them in a week, I scraped the funds together and took one home. The usual test period and one ambi safety later, and they all lived happily ever after.