5 Lessons I Learned from a 24-Hour Long First Date
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“I’m going to fly out to take you on a real first date,” he said after our second video call.
I had just signed up for CatholicMatch only a couple weeks prior. After a few days of messaging, we had graduated to phone calls—I couldn’t believe we were already at the “flying to meet you” phase. “It’s better to see if we have a connection in real life sooner than later,” he said. I couldn’t help but respect how upfront he was.
So, he booked a hotel by me and we planned to spend Friday-Saturday together. I arrived at the airport to pick him up in my favorite pink sundress. He texted me, “Just landed! See you soon!”
And then we met.
After 20 minutes, I realized we had no chemistry offline. Yikes.
This is a common story. But it’s a risk we all take when pursuing love in a modern, digital age. As I looked ahead to the longest first date of my life, I knew I was in for a few lessons. And, boy, did I learn them.
Lesson #1: Have reasonable expectations.
With online dating, it’s hard to set up clear boundaries once you take it offline. Talking online and on the phone beforehand is a great way to get to know someone, but it can give a false sense of knowing exactly who they are. It’s easy to project an idea of who you think they are based on the curated information you’re given online or via phone. Meeting in person is the only real way to know if your online chemistry translates into real life.
After my date tried to initiate physical affection within the first 45 minutes of our date, I realized we were on completely different pages. I saw the date as a means to discern any interest whatsoever, he saw the date as a means to solidify the relationship. And let me tell you, the 23 hours left to our time together were even more awkward after swerving his advances.
Lesson #2: Keep it short.
Having reasonable expectations also means having a reasonable time limit to your date. It also allows for emotional prudence. Sure, we like to imagine the date unfolding like a montage scene in a rom-com where you laugh and talk into the wee hours of the night.
But let’s be real, is that healthy? With traditional dating, you meet for coffee or dinner. The encounter is 2 hours max. Afterwards, both parties are able to separate and think about the date objectively.
The longer my marathon date went on, the more I realized it was actually a super long visit—not a date. After the 5th hour, conversation was beyond dried up. Even if we had hit it off, spending over three hours engaged in intentional “first date” conversations would’ve been exhausting regardless.
Lesson #3: Plan breaks.
“Why didn’t we plan any breaks?” I internally kicked myself. Because he had flown to me, I felt a responsibility to host him in my city and keep him entertained. He also hadn’t rented a car, which limited both of our freedom to take necessary breaks from each other. I realized we could’ve made this much easier on ourselves if we had defined clear “date” hours where we’d spend our time more intentionally.
Now, I know it’s hard to plan breaks when someone is literally traveling to meet you. But asking your date to pick you up and drop you off at specific times is not rude or ungrateful—it’s healthy. Giving yourself and your date the courtesy of recharging is both respectful and prudent. Allowing for the opportunity to take a step back actually aids in discernment and provides a necessary breather.
Lesson #4: Plan activities.
Since he was visiting me, I was both literally and figuratively in the driver’s seat of the date. I made the big mistake of not planning any non-conversation based activities. Insert facepalm here. As we went from restaurant to restaurant and wandered around the city, we became increasingly bored.
Sure, a dinner date works for a 2-hour long meetup, but 24 hours? Planning to go to the movies, a concert, a local arcade, a bowling alley, an escape room—literally, anything would have broken up the date and made it less intense. Balancing activity with conversation is key.
Lesson #5: Try, try again.
You may think I regret this insanely long first date, but I don’t. I was tempted to think, “See! This is why I shouldn’t date online!” But really, I learned that I’m a rookie when it comes to dating and I got schooled in a big way.
Online dating forces you to date smart—you can’t be lazy or careless about boundaries. You learn to be intentional with your words and time. You learn a lot about yourself and how to approach getting to know someone else in a healthy way. It pushes you to be more mature in how you date, ultimately preparing you for when you meet the right one.
Sure, I made the mistake of planning a 24-hour long first date. But instead of deleting my CatholicMatch app forever, I hopped back on a couple days later and thought, “Okay, how can I do this better next time?”
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