Since you are already a Ruger owner, I recommend the Ruger LC9S or LC9S Pro. Quite inexpensive; about $350. They are the same size/weight as the original LC9, but are striker fired vs hammer and have a vastly better trigger. The difference is that the Pro model does NOT have a magazine or manual thumb safety. So you can have it in whatever configuration suits you best.
They have "melted" corners and conceal extremely well in either an IWB holster like the Crossbreed, or a pocket holster like the Remora (we have both). We have owned two of the original LC9s and now two of the LC9Ss. Of course, they are up-close personal defense pistols, and not range guns, but I recently hit my 10" gong 7 out of 10 shots standing offhand at over 25 yards.
A few folks on the Ruger Forum (
Ruger Pistols - Ruger Forum) have had minor problems, especially when they were first released, but Ruger Customer Service is superb and quickly takes care of any issues. Ours are fitted with the "iron on" Talon grips.
Now, for when even a small single-stack 9mm is hard to conceal, or just to ALSO have in your pocket for fun (ref: Jim Croche), it's hard to beat one of the several excellent models of the North American Arms .22 mini-revolvers. Anywhere from about $200 to $500 depending on model. I have the Sidewinder, fitted with larger "Black Widow" grips. The larger grips make it much more manageable to shoot accurately than the stock bird's head grips, at the sacrifice of only a little bit of concealability. They will soon be releasing a new edition of a beautiful breaktop "Ranger" patterned after the old Schofield design.
YMMV
- Jay