How many gears for a first bike?

I never learned how to ride a bike - everything was in walking distance when I was little and then everything cool was out of riding distance when I got older. I want to now.

I figure my budget is $500ish, and I think I'm looking at something like an Electra Townie. Uses - riding to the gym (a couple of miles), grocery store (about the same), around the neighborhood. They offer everything from a single-speed to a 21 speed, and I have no clue how many of those I might need. 3-5-8?

On a scale of 1-10, 1 being Nebraska & 10 being San Francisco, how hilly is it where you live/plan to ride?

1.5. Some long slow inclines, and a bridge over a highway, but mostly flat.

The area I live in is pretty flat too & w/ a standard 10-speed road bike, I rarely ever shift out of the second-highest gear when I'm just doing general about-town sort of stuff. I experiment with different settings occasionally while on longer rides, but even then I'm on that setting about 90% of the time, so I imagine you would be good with anything from a single-speed cruiser on up.

better to err on the side of extra gears perhaps? you might get the bug and want to go further faster steeper.

You can get an 18- or 27-speed bike for that budget, and if you're hoping to ride more and expand your horizons beyond the few miles you mention, you may as well go for one. A single speed (geared correctly) will be more than enough for what you've asked so far, but won't be as versatile for longer or hillier rides.

On the other hand, if you want the Electra style bike, then it'll really only be suitable for relaxed town riding now matter how many gears you have on it. There's no point in getting a heavy, causal bike and then huffing and puffing in a single gear half the time - you want comfort, so the more gears the better.

Are you not tempted by a sportier kind of bike? Not necessarily a racer, but maybe a flat bar road bike if you don't fancy drop handlebars? Something light and nimble might suit city riding better (and be more versatile out of town).

Your budget should get you a basic but decent new bike, or a better second hand bike.

I really don't know anything about bikes, the Electra just looked cool. Someone suggested another of their models to me, the Cruiser.

Any suggestion on a flat bar road bike?

I'll stan for 3-speeds pretty much any day -- I don't need more than that for getting around Bklyn/NYC, altho maybe some of the steeper bridges would be a challenge.