Dating : In Online Dating, The Best Opening Lines Are Also The Weirdest

In the past decade, online dating has gone from a wild experiment no one admitted they were trying, to a completely ubiquitous phenomenon. Your friend’s mom is making her profile right now. The man who rings you up at the corner store is swiping in between customers. Grindr is forever exploding with DMs like an active volcano.

This influx of new digital daters has led to a wave of activity which translates to both more options and higher potential for burnout. Among so many apps, so many faces, and so many swipes — it’s so easy to get lost in the routine of countless “Hey.” and “How’s your week been?” conversations.

Many find themselves overwhelmed and not really connecting with anyone at all — it can so easily become window shopping — just another way to entertain your perplexingly bored and simultaneously overstimulated mind.

As both a seasoned online dater and online dating advisor, I’ve seen and participated in countless exchanges and it’s shocking how often two incredibly unique individuals can use this technologically miraculous ability to find a complete stranger across the internet to have the most unrevealing, disconnected and humdrum conversations.

In light of this unfortunate reality, let me warmly recommend getting weird.

Like, real weird.

Some of the best online dating conversations I’ve seen have begun with lines like:

“I have a confession. I thought for years that TLC’s biggest hit was about a guy called Jason Waterfalls. He should have stuck to the rivers and the lakes he was used to, seems like.”

Be vulnerable, they said. Be honest, they said. This lead to a long conversation of misunderstood lyrics that was absolutely unique and delightful.

“Let’s start with the basics. Would you rather fight 100 duck-sized horses or one horse-sized duck?”

The internet is a beautiful and strange place. We leaned into that and the resulting conversation was bizarre and gave us something to build on.

“Before we do anything else, let’s make sure we have a chance: does the toilet paper roll go over the top or under?”

This began a heated and contentious conversation which we then joked was our first fight. It was wildly entertaining and an opportunity to be more unbridled in a low stakes way, while bringing some serious heat.

“Personality Quiz: big dogs, little dogs, or hot dogs?”

This resulted in a conversation that bubbled from cute dogs to creeping on people’s dogs on the street, to street hot dogs — and left much room for terrible dog-related puns.

Life is too short not to be a little out-there. And as much as we instinctively fear scaring potential partners away, with the wild influx of people on every online dating channel, there’s a huge benefit in the natural selection that comes from letting all your freak flags fly — the more you lean into your unique weirdness, the less you’ll have to weed through a bunch of potential partners who just won’t get you. Somewhere out there is someone who is just as into curly fries, googly eyes, and Doom as you are.

Share the strangest icebreakers (wink wink) that lead to great first conversations in the comments below!

Now we can all bask in the glorious weirdness.

P.S. We launched a dating app that helps you find a partner AND makes you better at dating at the same time! If you’re around the Boston area, click here to download it and become a member.

If you’re outside of Boston or don’t have an iPhone, click here to join the thousands of awesome people who are already signed up for our waitlist. We’re coming for you soon!