Picking the place for a date is a delicate balancing act—especially at the very beginning of a relationship. In fact, most women I know hate it. It can be a dreadfully exhausting guessing game of what “type” of place will make the best impression not only of you, but also of what you think of him. I mean, come on. What would you think if he suggested that you pick up a couple 40s at the corner 7-11 while he snags a handful of snack wraps from Mc’y D’s? Unless you’re dining on the tailgate of his pick-up truck overlooking the East River to do a little midnight star gazing, I’m guessing you won’t find his suggestion too charming. And even then?
On the other hand, what if you’re into that, and you find his unconventional approach endearing? He could be the prince charming you’ve been waiting for—ready to sweep you off of your feet in his Ford F150—gun rack, trailer and all.
There are SO many factors that go into picking the place, that there’s no simple formula. While spending the evening at a posh wine bar in Tribeca might sound like a romantic evening to some, it might make the rest of us gag. Every situation is different, and every guy is different. More importantly, you’re different.
When picking the place, don’t try to be a mind reader. Try and figure out what terrifies you. Are you worried that he’ll hate your favorite dish at that adorable vegan cafe down the street, or that he’ll hit on the waitress at Hooters? Once you’re actually on the date, you’ll quickly realize that it doesn’t matter how much the food sucks, how hot the hostess is, or whether or not the atmosphere makes you feel like you’re dinning in a school cafeteria. It’s the company that matters.
You also have to remember that living and dating in New York or Washington gives you a tremendous advantage. There are more restaurants, bars and coffee shops than you’ll know what to do with. And as overwhelming as that might sound, it’s actually a good thing. So when you’re ready to take over and decide where to take that lucky suitor, remember three things to avoid:
1. Don’t pick a place too close to home unless you’re planning on sleeping with him. Look, no one’s judging you, but let’s be real. We all know how quickly a couple of cocktails can offset our moral compasses—and being close to home makes it too easy. Just make sure you’ve thought through all end-of-night scenarios before you’re six drinks deep and homeboy starts resembling that hot teacher you pined over in high school. Before you know it, you wake up the next morning and realize you drank him from troll status to super model, and you’re still the one being schooled.
2. If you’re dating more than one guy, for heaven’s sake, don’t bring them to the same place. If no one’s claimed exclusivity, technically you can date as many suitors as you so chose. It’s not for me, but a lot of ladies like to keep their options open. If you’re in that popular camp, don’t poison the pot by accidentally introducing Mr. Tuesday with Mr. Thursday before you’ve decided which one you actually like. It’s just not worth it. And put yourself in his shoes. How would you feel if you ran into his super sexy, scantily clad Ms. Wednesday? I’m sure her killer legs and perfect ass will make a bigger impression on you than he ever will.
3. Unless you’re ready to foot the bill, don’t pick a place that serves liquid gold as an appetizer. There’s nothing wrong with having Champagne tastes. And by all means, once you’ve got him hook, line, and sinker, don’t be afraid to ask for a nice meal every now and again. But before you demand diamond-encrusted lobster, don’t assume he’s going to pay. While it’s always nice for the guy to treat, he shouldn’t have to do it all the time, and some guys won’t even pay on the first date. (Sadly, yes, men like that actually do exist). Keep that Amex handy so you don’t find yourself in the back kitchen elbow-deep in sink-suds earning your meal because your date forgot his wallet, or his class, at home.
Picking the place doesn’t have to be hard. Just stick to your gut. If you really like the guy, and you’re not dating anyone else, you have nothing to worry about. You’ll naturally want to share a special café, park or restaurant with him, regardless of it’s proximity to your home, or how many dates you’ve taken there before. Also, don’t be afraid to embrace your sense of adventure and suggest a place that neither of you has been to before. Who knows, it could become your special place together.