You've bantered on IM, made some good jokes with mild flirting about wanting to meet his new puppy, and discussed your passionate desire to raise children in the Maldives because exotic kids are always way more popular in school. Maybe not in middle school. But definitely in high school and college.
Now it's time to pick a location for your first meet-up. This is an intimidating prospect: toss one too many vodka sodas with a splash of cranberry down the hatch, reveal that you had one too many toes (it was amputated, okay!?) and she's out the door faster than you can say 20% off code at Intermix. (But only on the bad stuff or the really really expensive stuff where a 20% discount in pointless anyway. Why do they do this? The only valid items for the code are a $2400 mink thong and a bejeweled, distressed, dip-dyed, organic cotton Balmain t-shirt for $1600.)
1. Dinner, Drinks, or Coffee?
Now, you know my stance on coffee. I think it's stupid as a romantic endeavor, and it's too well lit and gross in Starbucks and you can see his leg hair shining in the afternoon light and it's just not going to get me hot and bothered.
Dinner is tricky. Do you really like him or her? Would you want to be stuck on a desert island known as Restaurant X for two hours without any toilet paper or soap and be forced to converse and eat a meal together? If not, then don't go for dinner. If you really like someone, it's a nice gesture. But you have to have some form of security in the fact that doing that cute thing with the noodle from Lady and the Tramp is appealing with DCHottiexx27 (with that name, maybe she belongs on Adult Friend Finder.)
Nonalcoholic -- well, I dunno how to help you on that. I gave a list of dates before on places for inexpensive and nonalcoholic dates, but honestly a shot or two is going to make this less painful. Mild alcoholism, potato potahto.
Noise level in a bar or restaurant is very important. Too quiet -- your lack of witty repartee is making those figurative crickets very, very loud. I can hear the waitress sneeze. Into my soup. Womp.
Too loud -- it's a disaster. You're shouting, you can't hear what he's saying, and before you know it, he's talking about hiking in Appalachia and you're talking about how interminable Eat, Pray, Love was.
"Have you ever tasted beetle?"
"I said, do you like the Beatles."
- "Why the hell are you asking me if I dated Don Cheadle? I told you already it was a one-time thing, I wish you'd get off it."
3. Low Probability of Running Into Someone You Know.
This is key if you're hot on the JDate circuit. Just tonight I ran into a boy I recognized from the site (glad to know you're back from Israel, how is your pediatrics residency going?) Cringe. But mostly amusing, because he was clearly on another JDate and watching someone else flirt is a delightful mixture of entertaining and horrifying. And then you think to yourself, do I really look that cheesy when I break out my best story about that time I was beer pong champion in college as a way to demonstrate that I'm fratty and somewhat of a lush?
An additionally worse prospect: running into someone you know well enough who will come over to the table. This is awkward and terrible. And you know it's happened to you. The forced introduction of someone you're on a date with. Who's definitely not your "friend." You barely know the guy, except that he loves Dave Matthews, which of course tells you absolutely nothing.
Oh hi Sara!! How was your trip to Anguilla? Uh, yeah this is...Jon. Josh? Oh, sorry. Well, um yeah. (We just met on an Internet dating site about three hours ago and I totally wasn't going to go out with him but then remember Kenny? Yeah we've been hooking up and he acted like a total dick to me so I decided to go out with Jed instead. Josh? Oh, sorry. I forgot you were still sitting here.)
4. Mid-Price Range.
This is important because if you go somewhere too expensive and you've picked it, you look like a dick. I suggest both Yelp and Citysearch to help you scope out locales. Don't drive yourself crazy, or into a Yelp Hole (see Urban Dictionary). You could go nuts reading all the reviews from the crazy people whose sole purpose in life is to comment on Yelp. "The string-beans were too green." Yes, they were.
It's good to ask friends for suggestions, just make sure they wont be there to watch you flirting and laugh and point til you turn purple.
5. Go Somewhere You've Been Before.
Exit strategies are very important. Be sure to pick somewhere you're at least familiar with the neighborhood, in case you have mistakenly contacted a boy who resembles Chewbacca, on a good day. Be polite, but then tell him your mother got in a freak hang-gliding accident (I know she's at home right now but my dad's a crazy inventor and they were taking turns jumping off the roof).
Anyway, I gotta go.