Flirting in person is an art—subtle, electric, impossible to fake. Flirting online, especially in digital dating platforms like WhatsYourPrice, is a different challenge entirely. It’s a high-stakes game of wit and timing, where every message holds the potential to spark desire or fizzle into oblivion. One misstep, and you’re ghosted or, worse, branded as cringe. But play it right, and you’re not just sending texts—you’re setting the stage for something unforgettable, a conversation that leads to a real-life connection.
So how does one strike that perfect balance between intriguing and try-hard? What’s the secret to sliding into DMs without face-planting into rejection? Here’s your guide to navigating the digital dating playground like a pro, empowering you to take control of your online interactions.
Step 1: The Strategic Like (A.K.A. The Digital Wink)
Liking a photo isn’t just a double-tap—it’s sending a message. But timing and strategy matter.
Like a recent post, but not the latest one. This shows you’re interested and paying attention without seeming glued to their feed. A little distance is a good thing.
Like more than one, but less than four. One is too subtle. Four is borderline obsessive. Two or three? Just right. It’s never a good idea to appear over-eager.
Avoid ancient posts. Liking something from 2018 screams, “I was deep-diving your profile at 2 AM.” It’s a little weird, and few recover from that.
Bonus move: If they like something back, it’s a green light for Step 2.
Step 2: The Art of the Comment (Leave a Mark, Not a Mess)
The comments section is where you set yourself apart from the sea of heart emojis and fire emojis (seriously, be better).
Be playful. A witty or inside-joke-style comment will always win over basic compliments. Keep it natural and fun.
Engage, but don’t overdo it. If they reply, great! If not, don’t force it. Let any conversation that may happen, flow naturally.
Avoid generic one-word comments. “Nice” isn’t flirty. “Cool shot” isn’t memorable. You’re missing an opportunity if you’re not adding to the conversation.
Example: They post a beach pic? Don’t just say “?” (yawn). Say something playful like, “And the real reason behind global warming is revealed.”
Extra move: Did they like your comment or reply? Welcome to the DM Zone.
Step 3: The DM Slide (Read the Room, Then Make Your Move)
The DM is where it all happens—but the approach is everything. No one owes you a response, so your opening line has to land and strike just the right tone. But don’t stress out about it—we have some tips for you.
What NOT to do:
“Hey.” (Boring. Adds zero value. Single words will truly not get results.)
“U up?” (Only acceptable if you’re texting an owl.)
“You’re hot.” (They already know, probably. You need to stand out.)
What to do instead:
Reference something from their post. Keep it light and show that you are paying attention. (Example: “I need to know—was that pasta actually as good as it looked, or was it just for the Insta?”)
Use humor. A clever or playful message gets attention. If funny is hard to pull off, go for something with a relaxed touch.
Ask a light, open-ended question. Something that invites a response, not just a like. Questions that force a basic “Yes” or “No” answer don’t open up a line of dialogue.
Extra move: You’re in the game if they respond with more than just an emoji.
Step 4: Keeping the Vibe Right (Avoid the Ghost Zone)
So you got a response—now what? The goal is to build momentum, not kill the vibe.
Match their energy. Don’t go overboard with long paragraphs if they give shortish (but interesting) replies. Reply with a message of matching length.
Mirror their texting style. Playful? Keep it fun. Deep convo? Lean in. Nothing is worse than someone leaping from banter to heavy stuff in one move.
Know when to move to IRL. Suggest a casual meet-up if you’ve been talking for a bit and the chemistry is there. No pressure, no overthinking. Generally, most people don’t love endless texting, so the shift to IRL will be welcome.
Red flags to watch for:
- If they only reply with emojis or “lol.” (low interest)
- If they take days to reply, but are active on social media. (you are not a priority)
- If they dodge plans but keep chatting (enjoys attention, not looking to meet), they could do this for the thrill of the text without intention to follow through. Indeed, they may not be single. Prof. Gurit Birnbaum’s research suggests that some flirty matches might not be looking for something serious—they could be using DMs to escape the monotony of their current relationship. So before getting too invested, consider whether you’re a spark for their boredom rather than a genuine romantic prospect.
Pro tip: Don’t force the connection. If they’re not engaged, move on with confidence.
Step 5: The Exit Strategy (Gracefully Recovering from Cringe)
Mistakes happen. Maybe you sent a DM that didn’t land, or you suspect you went a little hard in the comments. What now?
Play it cool. Don’t apologize. Don’t double-text. Just let it breathe. Let them deal with it.
Own it, if necessary. If you went too bold, a self-aware message like, “Okay, that was way aggressive. My bad. ?” can reset the tone, if you truly feel the need to do that.
Know when to walk away. If the vibe isn’t there, forcing it only worsens it.
Make It Fun, Not Forced
Online flirting isn’t about chasing—it’s about connecting. The key? Keep it playful, be confident, and most importantly, be yourself. If it’s meant to click, it will. If not? There’s always another double-tap waiting to happen.
For WhatsYourPrice users, mastering online flirting isn’t just about crafting the perfect opener—it’s about standing out in a space where first impressions really matter. Whether you’re the one making the offer or the one receiving it, a well-played message can mean the difference between an instant spark and a conversation that dies before the date is even set. By understanding how to keep the banter engaging, build intrigue, and show genuine interest, you can turn an online chat into a high-value first meeting—and set the tone for something even more exciting. Now go forth and DM responsibly.
