Margarita Confessionals: How to take the monotony out of dating

It’s Margarita Monday! Each week, we’ll be publishing a story about dating by Lauren Levine and/or Ali Washburn to go along with the latest episode of “The Margarita Confessionals,” a podcast for the jaded dater. You can find it on Soundcloud or iTunes.

When you’re dating, inevitably you’re going to answer the same basic questions over and over again. It’s the nature of the beast. However it’s also tedious.

Some of the inquiries you’ll field most regularly include: What brought you to Charlotte? What do you do for work? What do you do for fun? What part of town do you live in? How long have you lived here? Where are you from?

While it’s important to let the other person know some standard information about you, hitting these same topics repeatedly as you go through the dating process also has a way of making the whole thing feel weirdly like a job interview. So how do we take the monotony out of dating? A few thoughts:

Stop copying and pasting your messages on dating apps

If you’re the one starting the conversation, put a little strategy into the message. If the person has anything in their bio that would enable you to break free from a cookie cutter conversation, use it. Do they talk about their love of craft beer? Cool! Focus on that.

If they’re bio-less, look at their pictures. If he’s got one of those shots of him cradling a small tiger, do us all a favor and ask what the deal is.

Enough with the Miss America responses

If you’ve ever watched a beauty pageant, you know that there’s a question and answer portion where the contestant is given a major world issue and then asked how she would solve it. She gives a sugary sweet answer with no real substance but infused with plenty of buzzwords, and then smiles as she sidesteps her way off the stage.

When you’re on a first or second date, it can feel like you need to be that way. You want everyone to like you and you’re not comfortable enough with your date to let your real personality come through. As a result, you start responding to questions with answers that lack authenticity, but would totally knock the judges’ socks off.

For everyone’s sake, don’t try to be Miss America when you’re dating. If you’re sarcastic, let it show. If you’re a sports nut, perfect. If you want to travel always for the rest of your life, say that. You don’t have to try to be everything for everyone. If this one particular person isn’t buying what you’re selling, someone else will.

Don’t rely so heavily on conversation

Sitting and talking for two hours puts a lot of pressure on both of you, so don’t be afraid to do more than one activity on your date. Get a drink, but then go to Abari and play PacMan. Shoot some pool. Take a walk on the greenway.

It gives you stuff to talk about, plus it’s more fun than just staring at each other, praying you don’t enter into a horribly awkward silence.

Lastly, come equipped with a few great stories to share. Weird first jobs. That time you backpacked through Europe. You know you’ve got something interesting to talk about. Not only does this help with silences, but sharing these tales also shows your date who you really are, beyond the standard five questions everyone always asks.

Photo: Rémy Thurston