There was a time—not that long ago—when going on a date meant meeting a complete stranger. You didn’t know their dog’s name, their Spotify Wrapped, or what they looked like in 2016. You had no mutuals. No mutual trauma. No ex’s to stalk and no soft-launch timeline to study. You just… showed up and figured it out in real time. Revolutionary, I know.

Fast forward to today, and we are terrified of dating people we don’t already know through 3 degrees of social proximity and a verified Instagram grid. We want mutual friends. LinkedIn profiles. A TikTok trail. A vetted past. We don’t go on dates—we do background checks. But in trying to eliminate all risk, we’ve accidentally removed the magic, too. Grab a glass of wine, and let me explain how..

Dating Apps Became Mini Résumés

Apps were supposed to introduce us to strangers. Instead, they’ve turned into digital dossiers. We scroll like we’re reviewing applications—not meeting humans. Where they went to school, what they do for work, their political alignment, their height, their gym routine, their love language, and ideally a photo with their mom to prove they’re emotionally available... it’s an overload of information that’s stopped us asking “Could this be interesting?” And instead has us asking “Could this be safe? Could this be perfect? Could this be predictable?” In other words: we’re not dating—we’re scouting for risk-proof romantic investments.

Familiarity Isn’t Chemistry

We’ve convinced ourselves that dating someone who feels familiar will make things easier. That if we date someone with the same favorite band, the same group of friends, the same social references —we’ll skip the awkwardness and jump straight to compatibility. If we share hobbies, humor, and hashtags, the relationship will practically build itself, right? Not quite.

What we’ve actually done is build a culture of dating that prioritizes familiarity over discovery. And in doing so, we’ve flattened the experience. Because when someone already fits the mold, there’s nothing new to learn. No real questions to ask. No nervous “I wonder…” flutter that makes dating electric. It’s safe, sure. But it’s also predictable.

And when everything feels like something you’ve already seen before, it’s hard to stay curious. Hard to feel challenged. Hard to fall. This is where dating gets stuck. Not because you’re doing it “wrong”—but because you’re not letting it surprise you.

Part of dating—real dating—is the unknown. It’s asking questions you don’t already know the answers to. It’s finding someone’s weird, wonderful, totally unexpected inner world and falling for that. True connection isn’t about perfect alignment. It’s about engaged exploration. It’s discovering a story you’ve never heard, a perspective you didn’t expect, or a part of yourself that only shows up when you’re around them.

When Everyone's a “Maybe,” No One's a Yes

By trying to pre-screen the perfect match, we’ve built a culture of permanent hesitation. If they’re not vetted, we don’t meet them. If they don’t pass the vibe check by photo slide three, they’re out.  No second chances. No curiosity. Just: Next.

And if they do make it through the filters? We show up to the date half-committed, emotionally guarded, and still mentally keeping tabs on what’s waiting on the next app over. A better option. A shinier match. A person who feels 2% more aligned with the made-up fantasy version of our “ideal partner.” The date isn’t a connection—it’s a placeholder. A maybe. The problem is: when everyone is a maybe, no one gets a real yes.

We’re not choosing people—we’re postponing the act of choosing. We spend so much time collecting possibilities that we forget how to actually invest in one. We assume the spark should be instant, the conversation should flow perfectly, and if it doesn’t feel like a movie in the first 15 minutes, it’s a waste of time.

That’s not dating, babe. That’s romantic consumerism. And it’s making us miserable.

So What Does FROM Do About It?

At First Round’s On Me, we believe in strangers. We believe in showing up before you’ve dissected someone’s dating history like a true crime docuseries.

Here’s how we bring back that first-date thrill—without the chaos:

• You send a real date invite—Drink, Time, Place. Not a vague “we should hang sometime.” Not 16 days of “wyd” texts.  You’re not auditioning—you’re initiating. That’s clarity. That’s confidence. That’s how real dates actually happen.

• The chat unlocks 24 hours before the date. Just enough time to break the ice—not enough time to overthink, spiral, or get stuck in a pseudo-relationship with someone you’ve never actually met. We’ve all been there: texting for weeks, getting emotionally invested, and then poof—they’re gone. FROM cuts that loop before it even starts. You connect right before you meet, not long before they disappear.

• You only get one confirmed date a day. Why? Because dating isn’t a numbers game. When you’re not overwhelmed by options, you make space for intention. One match a day means you actually see the person in front of you. It forces you to slow down, pay attention, and engage without the pressure to juggle five conversations or optimize your romantic ROI. You’re not collecting people. You’re connecting with them.

No over-research. No pre-stalking. No analysis paralysis. Just two people. One drink. And some damn curiosity. That’s it.

FROM wasn’t designed to keep you in the app. It was built to get you off it—as quickly, safely, and authentically as possible.

The Bottom Line is, you don’t need another mutual friend. You don’t need to vet their Instagram stories from 2019. You don’t need to feel 100% certain before you meet them. You just need to meet them. Safely and in public, of course. Because real connection starts with a little mystery. A little risk. A little willingness to step into the unknown and say, “Sure. I’ll grab a drink with someone I don’t know (yet).” So, let’s stop dating people we already know… and start getting to know the people we date. Until next time x