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Shoot as many friends' weapons and/or rentals as you can. It's interesting to find out what various new shooters like, and why, after they experience shooting a fairly diverse selection of handguns.

Or you can go down the road of acquiring one, then another, then another, and repeat as many times as it takes to finally realize you'll never get it exactly right. But that's part of the fun, too, yes?
 
A Glock M17 or M19 is a good place to start, as 9mm ammo doesn't have a hard "kick", and the ammo is easy to find...Also, the pistol is VERY easy & simple to operate and strip-down for cleaning.
 
I'm old school and prefer revolvers, left or right they shoot the same, double action (preferred) or single action and no cumbersome safety to mess with.
.22's are fun but I would opt for a 32 H&R mag or 357 mag cause you can shoot the lighter versions (32 S&W or 38 Special) for practice & plinking and
the mags for serious work. The same goes for 44 mag/special
 
Add a little cash to 300 bucks and you could get a sig 2022 chambered in 9mm. Ammo now is hard to find I'm sure, but usually 9mm is pretty easy to come by. The 2022 is a double to single action with a decocker.
 
Good point Tahoe. My 6" barrel .357 mag pistol (S&W 686) has been a favorite for decades. And for most of my friends, big and little.

I can hardly conceal it (without a briefcase). It's holstered on my belt when I go shooting so I'm never unarmed. Then at some point, I blow 50-100 rounds through it and chase cans around. Excellent instructional piece. Gentle and unintimidating with .38 wadcutters, graduating into magnum rounds when the shooter is ready.

Single-and double-action, it helps identify and eliminate flinching problems for experienced shooters, as well, with a mixed load of .38/.357 (and a couple sneaky spent rounds in there to reveal "yanking," etc).

Cheap to shoot, super accurate and versatile. Like and old friend, it's my favorite for sure.
 
Glock 19. If you decide to move on you will never have a problem finding a buyer. You will have lots of after market mods available, accessories, and etc. You can find them used or new at reasonable prices (usually). It willgive you a lot of versatility in choices down the road (target, cc, etc.).
I also strongly agree with the suggestion for a .22 revolver. Hard to go wrong there.
 
I would suggest trying a Glock 19 Gen 4. They are easy to shoot and clean, reliable and moderate in price. I have several pistols but like my Glock 19 the most.
 

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