Many people are daunted by first dates but, over time, I’ve realized that I’ve been most daunted by second dates. First dates usually consisted of meeting for a happy hour, a meal, or really anything involving alcohol. Consuming a few drinks led to an ease in conversation, which I mistook for an authentic, emotional connection. While a little liquid courage may have helped get me through first dates, I would frequently find myself on disappointing second dates.
This first occurred two years ago, when, 10 minutes into a second date, the conversation came to a grinding halt. I was trying to reference something we talked about on our first date, but I just couldn’t remember anything substantial about our conversation. We didn’t really connect on our first date, but the consumption of a few drinks made me think we had. Realizing I had wasted both my and my date’s time because of this, I apologized and left relatively quickly. Once I started going on sober first dates, it was easier to gauge which conversations were simply surface-level, and which ones sparked true, authentic connection.
Even now, in my long-term relationship, we always make sure to schedule day-dates in addition to evening ones. That way, we can enjoy each other’s company in a different, more meaningful way. By meeting over an activity, we learn more about each other than we would at a bar, when the only activity (besides drinking) is staring at each other while searching for topics of conversation. Here are my favorite sober date ideas:
Sketch in the park
Full disclosure: you do NOT need to be an artist to do this! Grab some paper, colored pencils, and a picnic blanket. Draw people, animals or flowers; the park is your oyster. If you run out of things to sketch, you can draw each other! (A very not-so-subtle way to check out your date’s beautiful face.) For our most recent anniversary, my boyfriend and I took it up a notch: We chose photos off of each other’s Instagram pages, and painted them! It went so well that we hung them on the fridge.
Go on a snack crawl
It’s like a bar crawl, but with snacks! It’s delicious, and you’ll stay grounded and sober. Choose a type of snack theme like french fries, ice cream, or smoothies, then choose a neighborhood in your area. Start at one location and then walk around to search for other places that carry the snack of your choice! Maybe your favorite spot can be the location for your second date? On my favorite snack crawl, I discovered the best vegan donuts in New York City. My boyfriend and I won’t go there without each other!
Visit the library
Stay with me! This is a free, lighthearted way to start deeper conversations with your date. It’s a great option for someone you’ve been on a few dates with and feel comfortable around. You both find your favorite childhood book, find a cozy spot in the stacks, and explain to your date why you loved this book as a kid. Then you check out the books and read each other’s favorites! You can do that part separately or venture to a cozy coffee shop and read together.
A surefire way to get to know someone’s heart is to volunteer or do random acts of kindness with them. For example, my boyfriend and I take time during the holiday season in December to make bags with some essential items for the homeless community. Over the course of the month, we go to stores together and gather essential items that we then hand out during the holidays. Find a cause that you and your date care about and give back to your community.
Storytelling at the art museum
Going on a date to your local museum is not a novel idea, however, have you ever tried going to an art museum and making up stories about the people in the paintings? I’ve actually been the person who models for portrait paintings, so I can tell you that the people in these paintings had to sit still for many hours! What were they thinking on the day they posed for the painter? Were they thinking about their next meal? Were they in a secret romance with the artist? Making up the thoughts or backstory of the person in the painting is a way to get to know your date’s sense of humor!
Don’t stress about making up a perfect story! The point of dating is to have fun and get to know another person. The more creative you get, the more likely is it that you’ll have engaging conversations.
Originally published on June 1, 2021.