First Dates: Breaking all the Rules

By R. Courtland
R. Courtland

First Dates: The Unwritten Rules, Awkward Conversations, and Why They Need a Glow-Up

Ah, the first date—the necessary evil of modern dating. We’ve all been there: trying to be charming, playing it cool, and, of course, dancing around the unwritten rules we all follow like it’s some ancient ritual. You know, no kissing (too forward!), no diving into deep conversations (too much!), and that awkward moment when the bill arrives. Let’s not forget the go-to conversation topics: “What do you do for work?” “Where did you grow up?” “Do you have pets?” Snooze fest.

But how did we end up here, trapped in this first-date hamster wheel of boring small talk and fake politeness? And more importantly, how can we evolve the whole first-date experience so it’s actually enjoyable? Let’s dive into the history, the unwritten rules, and—just to spice things up—some real tips to make your next first date anything but basic.

Where Did All These “Rules” Come From, Anyway?

First dates weren’t always about playing it safe. Way back when, courtship was basically a job interview, and women were supposed to be “modest” while men were expected to play the role of Prince Charming. The goal wasn’t to have fun; it was to assess whether you were a good candidate for marriage. Think of it as The Bachelor, but way more serious (and with fewer roses).

Fast forward to the 1950s, where “going steady” and diner dates became the norm. It was all about soda fountains, drive-ins, and stealing a kiss at the end of the night. Back then, the “rules” were simple: don’t mess it up and don’t push too far too fast. The result? You guessed it—awkward conversations about hobbies and what you did at summer camp. Even worse, it solidified the idea that first dates should be predictable and polite. Yawn.

By the time we hit the ‘90s, romantic comedies had brainwashed us into believing that first dates were the start of epic love stories. Cue the Meg Ryan and Tom Hanks films where small talk turns into soulmate-level connection. And just like that, we got stuck in a loop where first dates became a polite checklist of “get-to-know-yous,” leaving no room for real connection or fun.

The Unwritten Rules (AKA, Why Your First Date Feels Like a Script)

        • Be Prince Charming (or Princess Grace): Yep, we’re still doing this. Guys feel pressure to be the perfect gentleman—open doors, pay for dinner, the whole nine yards. Women? Play it cool and polite, but not too cool. This “etiquette” comes straight from old-school courtship, but does it really need to be this stiff?
        • No Kissing (or Sex) on the First Date: This one’s still up for debate in most circles, but the rule comes from those old-fashioned ideas of modesty and “playing it safe.” In reality, a kiss or no kiss shouldn’t determine the vibe—sometimes it just feels right, sometimes it doesn’t. Let it flow.
        • The “Safe” Small Talk: Name, job, where you grew up, and “do you have siblings?”—it’s like we’re all reading from the same boring script. You’re playing it safe to avoid any awkwardness, but where’s the fun in that?
        • Who Pays?: The classic standoff at the end of the night. Is the guy expected to pay? Should you split it? These days, people are more open to splitting, but it’s still one of those moments that feels unnecessarily awkward. Why is it so hard to just agree on this?

Why First Dates Have Become Predictable AF

Dating experts agree: we follow these rules because they’re comfortable. Think about it—first dates are nerve-wracking, and sticking to predictable conversations gives you a false sense of control. But here’s the catch: we’ve overdone it. Most first dates today feel like you’re playing a role in some tired old sitcom. And spoiler alert: no one wants to star in a boring episode of “How to Survive a First Date”.

It’s like a choreographed dance—you’re asking the same questions you asked on the last five dates, with the same polite laughs and nods, waiting for the moment when you can finally call it a night. But where’s the fun? The connection? The sparks?

Oh, and speaking of awkward moments: have you noticed how the ice-breaker jokes on first dates are usually terrible? If I had a dollar for every time someone made a joke about coffee being their “spirit animal,” I could fund a way more exciting date night.

The First-Date Price Tag: What’s the Real Cost?

The average cost of a first date in the U.S.? Around $120. That includes dinner, drinks, maybe a movie or activity. But let’s be honest—the real cost isn’t just financial. It’s the time and effort we put into prepping, planning, and then sitting through what often feels like a rehearsed job interview. And with apps like Tinder and Hinge making dates more accessible than ever, the stakes feel even higher to make that money and time count.

A Fresh Take: Let’s Reboot First Dates

It’s 2024, people. There’s no reason why first dates should still feel like they’re stuck in the ‘90s. Here’s how to switch things up and actually make dating fun again.

       

1. Use Technology to Get Comfortable First: Video calls aren’t just for Zoom meetings. Why not hop on a quick FaceTime or send voice notes before the date? That way, you’re already breaking the ice and skipping past the awkward small talk. This also gives you a chance to see if you vibe before committing to an in-person meet-up.
       

2. Ditch the Script: Instead of sticking to the same old “what do you do?” questions, get creative. Ask something fun like:
        •       “What’s the weirdest food you’ve ever tried?”
        •       “What’s your dream vacation, but like, if money didn’t matter?”
        •       “If your life was a movie, who’d play you in the lead role?”
These types of questions open up real conversation and, honestly, lead to more laughs (which is way better than nodding politely through boring small talk).
       

3. Do Something Different: Dinner’s nice, but it’s also predictable. Try something like a food truck festival, bowling, a comedy show, or even an arcade. When the pressure’s off, you’re more likely to relax and actually have fun. Plus, a little competition (hello, bowling) can break the ice in a more natural way.
       

4. Split the Bill or Rotate: Prince Charming is cool and all, but in 2024, splitting the bill or alternating who pays is way more common—and way less awkward. Talk about it beforehand if you’re worried about it being weird. You’re both adults; handle it like one!

Experts Say… Let’s Make It Real

Dr. Helen Fisher, an anthropologist and dating expert, says that the small-talk trap happens because people are afraid to open up too soon. “But asking open-ended, thought-provoking questions on the first date can lead to deeper emotional connections.” Basically, ditch the rehearsed stuff, and get real. You’ll know pretty quickly if there’s chemistry.

Matthew Hussey, a relationship coach, adds that confidence changes everything. “When you’re comfortable being yourself, you stop trying to impress and start actually enjoying the date. Authenticity is magnetic.” So, stop trying to be the perfect version of yourself and just be yourself.

The Future of First Dates: Breaking the Rules for Better Fun

Let’s be honest: first dates don’t have to be boring. By shaking off the old rules and bringing in more personality, we can make them less like job interviews and more like… fun. Get to know each other before you meet, ditch the predictable questions, and choose a date activity that makes you laugh. Oh, and don’t stress over the kiss thing—let it happen naturally, or not at all. Either way, it’s your date, your rules.

So, next time you find yourself planning a first date, forget the script. Make it fun, make it real, and don’t be afraid to break some of those “rules.”

Let’s make first dates exciting again. #FirstDateReboot

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