The worst first date of my life involved a beauty school drop-out, a weeklong search for weed and a dirty stuffed animal pulled from the back of an obese Cubs fan’s jean shorts. I took wrong turns at literally every opportunity in the planning of this travesty. In my defense, I was barely 21 and had no idea what I was doing, which partially explains why I asked out a waitress who ended up being a drug dealer of sorts and, not that surprisingly, the daughter of a convict.
We went to a Cajun dinner that she hated and an improv show that she hated even more. I learned a valuable lesson that day: the most important part of any first date is finding the right person to take with you. Next on the list is deciding where to go.
I grapple with this issue every time I go on a first date. Is it better to try and impress someone by taking them to the hottest, most expensive restaurant in town or are you better served by going to a casual spot where you can feel more relaxed? I don’t know the answer. I wish I did. I think there are points to be made for each camp. Buckle up, Heart Attackers, it’s time to explore The Fancy First Date Question.
A first date inherently involves trying to impress the other person. That’s just part of the game. You’re trying to say “look how awesome I am” so you can (a) go on more dates with this person and (b) possibly do some boot-knocking later. As part of that, it makes sense to take your date to a super-cool location to prove how awesome you are and set the expectation that your future life together will be filled with fancy awesomeness.
Unfortunately, you might find yourself next to a table full of douchebags. There may be service issues that you feel responsible for because you chose the location. You might not even want to drop major coin on a first date. Expensive restaurants are a serious investment these days. What if your evening turns out terribly? What if you and your date can’t go three minutes without falling into the uncomfortable void of silence that happens when two people realize they’d rather be at home watching House Hunters International? These are dilemmas you avoid when you opt for a more casual setting.
Going casual means you lose out on your glitz appeal, but you hopefully make up for it in substance. There’s not as much impressing going on with the venue, but that means that your personality takes the spotlight. For some dudes, that’s a major problem. For others, it’s a chance to shine. I like the atmosphere of a more low-key place because it gives me more of an opportunity to talk and, more importantly, listen. Casual places with good food allow me to put my best foot forward and all of my attention goes to my date instead of the models who have camped out in the corner booth to chow down on half-orders of arugula.
While it may seem like I skew towards the more casual locations, I actually prefer to go big on the first date. I go in thinking that it’s going to be a success, so I’d rather aim high and be disappointed. I don’t go all out, though. Instead, I try to be targeted in my approach. I find out what my date’s favorite food is and try to find the best version of that.
Or I suss out how adventurous she is and hit up the tiny Oaxacan place she’s never heard of. In the end, it doesn’t matter if you go fancy or not. Any restaurant is the right restaurant if you end up having a good date. Before you decide on the place, though, make sure you’re going with the right person. You don’t want to end up with the drug-dealing convict-daughter waitress. Trust me on this one.