“Excuse me, do you know how much a polar bear weighs?”

“No.”

“Me neither, but it breaks the ice!”

From the outright cheesy to the blatant booty call, pickup lines have yet to cease to exist. Unfortunately they continue to evolve—oftentimes with the day’s current pop culture (Google “Game of Thrones pickup lines” real quick for proof)—much to the chagrin of beautiful women having an after-work cocktail with girlfriends at a bar or those hoping to read their latest Amazon find in a quiet corner at a coffee shop.

And the pickup lines only get worse when they go digital—and every online dater is aware of this. With so many things that one can open a conversation with, it seems a large number of available men looking for connection via dating websites and apps continuously go for the usual suspects. Gentlemen: No one is impressed with your “Sup,?” “You up?” or “What brings you on [insert dating platform here].”

It’s important to remember that most everyone looking for companionship on dating platforms are doing just that: Looking for companionship on dating platforms. What’s “Sup” is that they want a date, if they’re answering your message that means they are certainly “up” and what brings them on is the hope that someone will cut through the noise and say something intriguing to them.

In a world where the majority of singles are finding dates on the Internet, pickup lines have become tired, trite and sometimes truly annoying. In a bar you might be able to get away with making a woman laugh by asking her to feel your jacket because it’s “made of boyfriend material,” but you need to stand out from the crowd when you’re surfing singles online.

Successful gentlemen these days really need to impress when dating online—and not just with their profile information. Sure, you might have a boatload of money, a Tesla in the garage, vacation homes around the world and a corner office in your city’s tallest skyscraper—but who’s to say the next thumbnail photo on a search doesn’t have those same things?

The answer? You need to think old school. You need to woo. You need to charm. You want the person you’re trying to date to think you are the person they’ve been looking for. Women also tend to actually enjoy the company of those who they choose to spend time with, so you really should be trying to show off some personality that exhibits why you’re the one to message back.

Our advice is to ditch usual lines and try to make a connection with your first message. Show your potential date that you have something in common with each other, make her feel special or illustrate that you paid attention to the details she listed in her profile. Taking a personal approach to starting a conversation—and not opening with the line you read in the latest Esquire article you read—just might spark a fantastic discussion that turns into your first date.

Read on for our tips of how to approach that first message—or first few messages—without coming off like a total cheese ball.

Zero In On a Profile Gem

Everyone is looking for something out of a potential partner. It might be looks, it might be success, it might be influence, or it might be the one who checks all marks on “the list.” At the same time, however, no one wants to date someone who bores them—no matter how good-looking or accomplished they are.

And to show that you can entertain the person you’re looking to land, you should show her that you can keep up an amusing conversation with her. Consider reading her profile and try to find something that you can ask her about. Does she enjoy hiking? Ask her about her favorite nearby trail. Are you from the same hometown? You surely know something only people from there are passionate about. Do you share a favorite sports team? Talk about their latest season.

Not only does this engage her in a conversation with you, it also shows her you took the time to get to know her a little. While other men might only message after seeing a pretty face and hoping for the best, you’re investing time in expressing interest—and she’ll see that.

Ask Her For Some Advice

Think about it: How great do you feel when someone seeks your counsel? They’re letting you know they respect you and your opinion, that they believe you to be an intelligent person regarding what they’re looking to learn, and that you can help them. It’s a pretty gratifying feeling—and your date is going to think that, too.

Maybe she is a yoga enthusiast and you’re considering taking the hobby up. Why not ask her for some advice on poses or studios in your area to visit. Maybe you’re a sports bettor and she follows your favorite team. It might be a good idea then to ask her what her thoughts are on the team’s performance to correctly assess the next game’s margins. Or maybe she’s gorgeous and into video games. Even if you’re an expert gamer, give it a shot and ask her some advice on getting through a difficult level on the latest selection you’re playing.

Send Her a Gift

Okay, in any other situation this would be creepy. Why? Because sending gifts to a gorgeous woman you’ve never met before a mutual friend’s party or at the next social event you’re at is … well, weird. But with Seeking’s new Wishlists feature, surprising with a fabulous present might be the best way to say “hello.”

Wishlists allows attractive members to curate lists of items they desire, which then can be purchased by established members directly on the site. Should you send something special, she’ll be notified via email that you sent the gift and has the ability to accept, alter or deny what you purchased. The trick here? Making sure it’s the right gift. But with a personally curated list, how can you go wrong?

Guess Something About Her

Usually, it’s smart to adhere to the popular phrase: “When you assume, you make an ass out of u and me.” But when you’re trying to express interest and stand out from the crowd blowing up the inbox of someone popular, it could be a successful tactic.

Why? Because guessing or assuming something about someone intrigues them. If you’re correct, they’ll want to know how you could hypothesize something correctly about them with so little background information to go off of. And if you’re wrong, they’re definitely going to ask you why you came to such a conclusion about someone they just met. It’s a win-win situation, really.

Just make sure whatever you’re summing up about her is something either flattering or neutral. Is her profile picture one of her on the beach? Does her profile mention being a Golden State Warriors fan? Ask her if she grew up in California. You get the gist, right?

Go Super OG and Introduce Yourself

“Hello! My name is [insert name here] and your profile caught my eye. How are you doing this evening?”

The ol’ tried and true: Simply saying hello can be subtly charming and thus exactly what someone who is inundated with “Sup, girl?” likely wants to hear. Just be sure to follow it up with more subtly charming conversation—you might even take another note out of this blog for your follow-up.

Sure, it’s basic. But it’s not going to rule you out. You know what will? That aforementioned line about falling from heaven!


Enjoying all the stories, advice and tips, and curious about Seeking? Create a FREE profile today and start experiencing the advantages of empowered dating and honest relationships!

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