Flirt Like a Pro

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How to Score an Online Date with Just One Phrase

They’re cute. No! Scratch that. They’re flawless. They’re rom-com meet-cute, drop your shopping and reach for the same apple as it rolls away material. You know you have to shoot your shot and to get that date, but it has to be perfect. No pressure, all you need is to flirt like a pro. That’s a lie. Major pressure. 

Cool it, we’ve got you covered.

Our dating pros know a thing or two about flirting online — and today, they’re sharing their best secrets with us! These aren’t opening lines, though. We’re getting you a date here, not getting you blocked.

This is a step-by-step guide to help you make your move and make it count. 

Welcome to Online Flirting, Pro Edition: Your SparkNotes to find the perfect phrase and get them swooning over you. You want to be funny and seem approachable. But trust us when we say that corny lines will only get you crickets (unless you’re Ryan Gosling or Adriana Lima. Which you aren’t, so we’ve got to work the personality angle here). 

The best way to slide into their DMs is with a message that feels authentic and shows your character; gone are the days of the pick-up line or the “wyd?”

Ready to take your online dating game to the next level? 

Step One: Let’s Get Real 

Giving good digital isn’t easy! You can’t just sidle up to him or her and splurge on expensive drinks at the bar to show off. The fact of it is that online flirting has to start with something plausible.

Show your dating potential from the get-go. To do that, do your homework.

  • Check out their profile. Take a look at their interests, what they’re looking for, and how they introduce themselves. This will give you lots of clues on the best way to slide into those DMs.
  • Start creating connections right away. Flirting is a muscle, and you have to use it. However, be yourself. Do they like sports and you’re more of a music fan? Bring up your favorite song from a sports movie and ask about theirs. Are they a doctor and you’re the creative type? Ask them which character they’d be in that one episode of Grey’s Anatomy.

Step Two: Say It Right

They say people think differently when they are behind a keyboard. Digital doesn’t allow for the ‘laugh it off’ slip-ups of IRL, and it’s that much easier to come across as a weirdo. If you want to flirt like a pro, you’ve got to speak the lingo. 

It’s not just what you say, it’s how you say it.
Here are some tips to liven up your chats: 

  • Express yourself! Don’t be shy to pair your message with emojis or gifs. The right meme at the right time is worth a thousand words (the wrong meme at the wrong time is worse, don’t go straight in with something crass or too obscure).
  • Keep it classy, with a bit of sassy. A naughty first message makes you seem thirsty— don’t be dehydrated. Being too formal is bland. Remember, there’s plenty of time to get racy (or have existential convos, if that’s what you’re into) once you’ve gotten to know each other. Right now, we’re going for a great message that catches their attention. 

Step Three: Embrace Your Inner Bruno, and “Leave the Door Open”

There’s a reason Bruno Mars is a master of seduction. Want to hit it out of the park with that first message? Give them a chance to talk about themselves and let them know you want to hear more in person. By leaving the door open, you make the other person feel flattered and excited to share how cool they are.

So, when you send that first message, resist the urge to talk about yourself. Instead, set the stage for them to show the best of who they are, hint at why you may be compatible, and make it clear that you’re interested in a date. This combo adds an actual allure to your opening phrase. 

Keep something back, make sure they have room to ask you questions.

Putting it All Together to Flirt Like a Pro

In the digital dating era, you’ve sometimes got to get mathematical about things— but, sometimes doing it by numbers can work wonders. Here’s your cheat sheet: 

Genuine Compliment + Why You Like Them + Open-Ended Question = Date 

Let’s break it down:

  • To offer a genuine compliment, you have to look through their profile and find those gems that caught your interest. 
  • When you tell the other person what you like about them, you’re adding something about yourself without making it obvious.
  • The open-ended question is your chance to let them know you’re interested.

Check this out. Here’s the formula in action: 

  1. Hey there! That’s a sweet DJ setup you’ve got. (This is your genuine compliment. Chances are, if they posted a picture of themselves with their DJ gear it’s because they’re proud of it.)
  2. Any chance I might catch you at Coachella this year? 😉 (Here, you’re sharing a bit about your interests and also letting them see that you may be compatible. The wink emoji is a playful touch.)
  3. I know a place downtown that happens to have a bigger vinyl collection than I do. They do good cocktails too, keen to check it out sometime? (This is a clear sign of interest and leaves the door open for them to take it from there. It’s also low pressure— it’s a casual meet-up to hang and chat about a shared interest in a neutral space.)

Smooth sailing, right? All you have to do now is log into your WYP profile and put this formula to the test. You’ll be amazed by the results! Check out more of the WYP Blog for more dating tips!


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