Margarita Confessionals: Land that second date by not being boring


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.

If you’re looking to land a second date, you don’t want your time together to feel like a networking event where you’re making polite but sterile small talk. At the same time, finding exactly the right stories to promote non-boring date conversation can be tricky. How do you show depth and personality in a way that doesn’t seem like you’re trying too hard? Here are some early date discussion topics that are entertaining to touch on:

Weird job stories

Have you ever had a boss straight out of “The Devil Wears Prada?” Did you have a job that was completely random and ridiculous but paid well? Did you have a co-worker who made Dwight Schrute look well-adjusted? These stories are always entertaining, even if your date is in a completely different industry.

Travel stories

Heading to a remote part of South America and camping out sounds like something I would do only if I was in a reboot of “Taken” and I had to do so to save the lives of the people I love. And yet a date once told me about such an experience and I was riveted. Whether you’ve been to the same place and can compare experiences, have never been and never hope to go, or it’s at the top of your bucket list, travel stories make for great conversation when you’re getting to know someone new.

High school stories

We’re all at the point now where we can laugh about who we were in high school. Unless you peaked in high school and wish you could go back and then that’s a different story… What were you like in 10th grade? The haircut. The clothes. The friends. The extracurriculars. Let’s hear it.

Experiences everyone can relate to

For those of us in our mid to late twenties, refrigerators are mostly just large, save-the-date holders, so interesting wedding tales have universal appeal. We’ve all encountered a bridezilla or two, unfortunately.

A story that shows what you’re all about and why you love what you do

If your dream life is going to a concert every single day, tell a story about the best/craziest/weirdest concert you’ve ever been to. If you love anything outdoors, talk about the most challenging hike you’ve been on recently. These stories add depth and show who you are in a way that a Bumble bio or a series of text messages just can’t. You know the whole “show don’t tell” concept your English teacher always told you about? Yeah, that.

For every great first date story, we’ve all been subjected to one that we wish we could have avoided hearing. Stories to steer clear of if you’re looking to snag a second date include:

Endless anecdotes involving lots of different people

This storytelling strategy works for “Game of Thrones,” but it’s not as effective when you’re trying to wow someone you’re just getting to know.

Tales involving extreme and recent drunken debauchery

No one expects you to be home playing checkers on a Saturday, but leading off the date talking about how you woke up in a stairwell wearing someone else’s shoes last weekend can send mixed signals. Wait until they know you’re actually a responsible human first.

Photo: Courtney Schramm


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