All, Dating

All Charm, No Cringe

Here’s How to Flirt Like a Pro

Flirting online can make or break your chances at a real connection. It’s a delicate balance of wit and charm, where the line between appealing and appalling can be dangerously thin. Standing out for the right reasons is crucial in a digital world flooded with overused pick-up lines and emoji-filled attempts to grab attention. So, how do you craft witty, engaging messages that spark genuine interest and make people genuinely excited to reply? Here’s your comprehensive guide to mastering the art of flirting online.

Understand Your Audience

The first step to effective online flirting is understanding who you’re talking to. It’s not just about throwing out random compliments or funny remarks. It’s about tailoring your approach based on what you know about the person so they won’t be weirded out. Take note of their interests, hobbies, and sense of humor. Are they into books, movies, or sports? Do their posts suggest they appreciate sarcasm and corny jokes, or are they more into straightforward communication? This initial observation is key to crafting messages that resonate personally and will give you the confidence that you’re on the right track. 

Opening Lines That Work

Forget “Hey, how are you?” as an opener. In online dating and social media, that can come off as bland and forgettable. Instead, kick things off with something memorable. You only get one shot. If their profile mentions a love for a particular movie, start with a quote or a fun fact. If they got a photo at a travel destination you recognize or find intriguing, bring it up. The goal here is to start a conversation that shows you’re interested in more than just their looks because, let’s face it, they probably have plenty of other people complimenting their looks in their messages. We don’t want our message to get lost within the other “Hey, you’re hot” DM’s. This approach will engage the other person and make you more excited about the conversation. 

Woman flirting on SMS
“u up?” “Yes, I’m texting with someone who knows how to properly flirt.”

The Wit Without The Cringe

When used correctly, wit in your messages will be your secret weapon. It shows intelligence and can make a conversation more engaging. However, the line between witty and cringy is often a matter of timing and context. Here are some quick tips:

  • Keep it light. Humor should not feel forced, so if you’re trying too hard, it won’t work.
  • Be self-deprecating, not self-defeating: A little self-deprecating humor can be endearing, but too much can come off as a lack of confidence.
  • Avoid controversial humor: Avoid jokes about sensitive topics until you know someone well enough.
  • Be bold: Don’t hesitate to step out of your comfort zone. Boldness can be attractive when used to express genuine thoughts or feelings. 

Compliments That Don’t Feel Forced

Compliments are a staple of flirting, but it’s essential that they feel genuine and not overbearing. Focus on complimenting someone’s personality rather than their looks. For example, complimenting someone’s taste in music or books can be more meaningful than just commenting on their pretty eyes. It shows you appreciate the decisions they make about their lives, which will make them feel good about themselves and possibly more open to sharing. 

Woman showing off flirtatious texts
And possibly even sharing with others!

Ask More Questions

Asking questions is a fantastic way to keep the conversation flowing and ensure the other person knows you’re interested. The key is to ask more open-ended questions to avoid receiving simple yes or no answers. Instead of asking, “Did you like the movie?” try, “What is your take on what the movie was trying to portray?” This not only keeps the conversation alive but it also sets the stage for a more meaningful segue. If you don’t want to get that deep just yet, maybe try something like, “If there were to be a sequel to this movie, what do you think will happen?” Be vigilant of your questions because you also don’t want to come off as too invasive, especially if the conversation is brand new. For instance, you could ask about their favorite travel destination and why they love it or about a book they recently read and what they found interesting about it. 

Timing Is Everything

Understanding the rhythm of your conversation can significantly improve your online flirting game. If you sense the conversation is lagging or they might be busy, don’t force it. Don’t be the person to blow up someone’s phone with messages; instead, take time to craft thoughtful responses. If they haven’t responded, just have a bit of patience. Remember, not everyone is glued to their phone 24/7, and they might have other things going on in their life. So, it’s okay to give them some time to respond. In fact, it can even make your conversation more interesting when they do respond, as they’ll have more to share about what they’ve been up to. 

Digital Etiquette 

Lastly, remain respectful. Flirting should always be fun and consensual. If someone doesn’t respond to your flirting or give the same energy back, it’s essential to recognize that and maybe take a step back. If you try to force it, it will only make things uncomfortable. Remember that the goal is to make the other person feel good about themselves and their interaction with you. This digital etiquette will not only make the other person feel respected but also make you feel more considerate in your approach. 


In conclusion, mastering flirting without being cringy is about balance and awareness. It’s about being clever and witty but not overbearing, funny without being offensive, and appearing interested without being invasive. Following these guidelines ensures you are stepping up your flirting game and making every conversation count. Practice makes perfect, so whether you’re on a dating app or sliding into someone’s DMs, remember that at the end of the day, flirting is a desire to connect with someone light-heartedly. Keep it classy and respectful, and don’t be afraid to be yourself. Rejection will happen; it’s a part of the journey. You just have to brush it off because you might be the juiciest, sweetest peach, but some people just don’t like peaches.