Make Sure It Is In Fact A Date
These days it has become confusingly common practice to just "hang out" with someone. This ambiguous and muddling invite will probably cause you to get all dressed up, go out with someone and spend the whole evening with the added anxiety of not being sure if this date is really a date. Ambiguity sucks, so if your'e the one doing the asking, for heaven's sake, just make it clear that it's a date, and if you are on the asked side of the equation, trust me the ten seconds of embarrassment for the misunderstanding are so much better than a whole night's worth of confusion (not to mention if you hug at the end really warmly, that will earn you another week of frustration).
So, now that you are both sure you are actually on a date:
Pick Somewhere Nonthreatening & Inexpensive
Try and pick a quite bar, or an out of the way coffee shop. Someplace without really loud music (so you can actually hear each other, thus speeding along the getting to know each other portion of the evening). Also, don't go to your favorite coffee-house, you know the one where all your friends hang out, because there is nothing that spoils the mood more than having to prematurely introduce your date to like everyone you know. Lastly, dating is expensive (especially if you're doing a lot of it), so maybe stick to one beer, or cup of coffee.
Make Your Own Way There
Awkward car chatter is THE worst! But more importantly, if the date goes badly you really don't want to have to add another thirty minutes onto it. Plus, it may end up snubbing your escape plan if they turn out to be completely insane, or you know, there just isn't any chemistry. Moreover, if you just met this person on OK Cupid (or some other website of your choice), you may not want them to know just yet where you live.
Dress to Impress (But Don't Go Overboard)
Shower, shave, put on some clean clothes. Look like you made an effort (because it shows the other person that you not only know how to use the shower, but that you cared enough about the meeting to make a little effort).
Keep the Conversation Light
Stay away from conversation ice-bergs like politics, dead relatives, exes, career malfunctions, childhood traumas, and so on... Just spend the time getting to know the person sitting in front of you, but don't overdo it, leave some mystery for next time. Think of coffee as an interview for a second date. Just get enough basic info and a feel for them to see if you would like to see them again.
This isn't an interview or a talk show, you both should get an equal amount of time to talk, and listening to what they have to say is also a good idea (for future reference of course).
Keep Your Cool
There is nothing worse than sitting in front of someone speechless, awkward and flustered (not to mention pit-stains). So get it together, down a shot of vodka, call your mum, or do some yoga! Just find a way to relax before the date. Go someplace you will feel comfy, have the date on your terms! Pick a coffee shop that you like, or a bar that serves your favorite comfort-cocktail. Just don't over-think it, you're either going to like each other, and hit it off, or never want to see each other again out of sheer awkwardness.
Watch Out For Deal-breakers
There really is no way of being P.C about this, we all have a list in our heads of things we won't put up with NO MATTER WHAT. So, even if this person is really lovely, but you know that you'll never ever date a cat owner again (because you are deathly allergic, and that one trip to the ER was enough) than maybe it's a good idea to end the evening as friends.
Don't Overwhelm Them
First dates should be casual; casual dress, casual location, casual conversation. Try and keep your skeletons locked up for the evening. You probably don't even know this person, and you haven't even decided if you will ever see them again, so maybe keep the heavier stuff for a little bit further down the line.
The Person Doing The Asking Is Doing The Paying
I am of the school of thought that a date is no different from a business lunch, or dinner with your parents. Whoever invited the other person to go out should pick up the tab, it's only polite. Moreover, if you only had coffee it shouldn't cost more than a few dollars, so don't try and get all philosophical about the tab, just pay it. Also, if you are paying it, do it smoothly and gracefully, refrain from awkward comments and remarks and, just give your date the feeling that it was your pleasure to treat them.
Initiate Contact
Look, first dates are confusing enough, and no one is quite sure where they stand, kissing your date good-night just lets them know you're interested (plus, it may affect your decision if they use too much saliva or tongue).
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