Matt, truth is, you'll end up carrying at least 6 different guns in the first few years you carry. The question is which one will you get first. The Glock is a good start. But they're double stack and that makes them fat and bulky, so they can sometimes be hard to hide (G30 especially.) You may WILL eventually end up wanting a thinner gun for times when you can't conceal the Glock. A good 1911 is a good choice, but a government model can get about as hard to conceal, due to the length of the grip. An officer's size 1911 is much easier. Yes the 1/4" of length does make that much different sometimes. And Let's face it, sooner or later you WILL get a mouse gun (I have a couple Kel-Tecs. One in .32, and one .380.) for when you can't carry the bigger ones. Oh, sure, I said I'd never carry a .380 or .32 as an Only gun, but that changed when I started working where there was a no weapons policy. My favorite one of mine to carry is my S&W J frame. It's a 649 in .357 Mag. If you see me wearing something with pockets, I have it on me. My Glock and 1911's have to be left at home when I have to have a tucked in shirt. But since it fits in my pocket, I can carry it always. Same reason people like their LCP's and Kel-Tecs. Best way to decide, and most fun, is go to a range where you can rent a good selection of pistols or get together with buddies who have pistols and go to the range. Shoot a bunch of them and see what you like. My first gun I carried was a Ruger P90.