Choose a bar that isn’t too fancy, but isn’t too dive-y.
Go to a chain restaurant. Ever, really, but especially not on a first date.
Select a bar with good lighting. Everyone looks better in low, warm, incandescent light.
Take your date to your usual hangout. It's cool if you know the bartender where you do end up going — in fact, it may be a plus to have an ally behind the bar — but you don't want to walk in and have everyone there shout, "NORM!"
Choose a bar with decent music and a good crowd, but isn't too loud or too mobbed.
Go to a bar where they allow smoking. If you happen to live in the rare city where smoking is still allowed inside bars, avoid them at all costs, even if both of you are smokers.
Pick a bar where some manner food is served.
Order dinner. Remember, this date has an expiry time, an hour or two; three at the most, but only if it’s going well.
Drink good booze. Whether you drink beer, wine, or liquor, order the nice version of your usual poison of choice.
Drink too much. One or two cocktails ought to be enough to smooth out any rough spots in this heightened social experiment, but three or four might put you over the line into red-faced and sloppy.
Drink before your date. I've encountered this over and over at my bar: an anxious suitor shows up 20 minutes early to put a few away before their date arrives, and ends up a boozy mess for the date itself.
Order for your date. It's pushy and can come off as pretentious.
Tip your bartender. Well. This may sound self-serving — because it kinda is — but a show of generosity to the person taking care of you will go a long way to making your date better.
Make a big show of your generosity to your date, or your fat bank account, or any other aspect of your healthy finances.