Hey, Connell. I consistently match with women on Tinder and Bumble, but the conversation often fizzles out over text, and they lose interest. It’s incredibly frustrating to see promising connections go nowhere. What are your best tips on how to flirt better over text?
—Harold, 35, New York City
Harold, I understand your frustration completely. It’s a common scenario: you make a great connection online, get her number, and then… silence. It feels like you’re so close, yet so far from turning that match into a real date.
The good news is, you can definitely improve your text flirting game and start turning those digital connections into real-world dates.
Let’s first understand what flirting actually is. At its core, flirting is playfully and charmingly expressing your romantic interest in a light and unambiguous way—definitely steering clear of anything vulgar.
The digital age has gifted us with a plethora of tools for text flirting: words, voice messages, pictures, and emojis. You have more ways than ever to text your way to romance.
However, many men stumble when flirting over text. They might come across as overly eager and flattering (“You’re incredibly beautiful and amazing!”), just plain friendly, or fall into the trap of boring, generic openers (“Hey,” “How are you?”). These approaches simply don’t cut it.
Here are the essential dos and don’ts to effectively flirt over text and make a lasting impression.
DO Make Your Romantic Intent Clear
It’s crucial that the person you’re texting understands you’re flirting and doesn’t mistake it for platonic friendliness. Subtlety can be charming in person, but in text, clarity is key. If your romantic interest isn’t clear, your flirting efforts will likely be ineffective.
Think about the difference between saying, “I can’t stop thinking about you,” which clearly conveys interest, versus, “I was just thinking about you,” which could be interpreted as just friendly.
While cleverness is a bonus, clarity should always be your priority. If you’re unsure, be direct. You could say something like, “By the way, I’m really enjoying getting to know you romantically,” or “Hey, you know what I find really attractive about you? It’s the way you…” and then tell them something specific you appreciate.
DON’T Use Boring, Generic Openers
Most women are inundated with dull openers like “Hey,” “Hi,” or “How’s your day?” These lazy clichés are a major turn-off. To stand out, your openers need to be personalized and engaging. Aim to give her something of value right away—a funny joke, a genuine compliment, or an intriguing question that she’ll actually want to answer.
Instead of the played-out “How’s your day?”, try something more original and engaging like, “I saw in your profile you have a dog – how did you choose their name?” or “Since you mentioned you’re a wine enthusiast, what’s your go-to wine bar in the city?”
Clichés are chemistry killers. Keeping your texts light, personalized, and directly related to her profile or previous conversation is the way to spark a connection and make her interested in continuing the chat.
DON’T Get Too Sexual Too Soon
In the initial stages of texting, keep your messages generally G-rated or PG. Becoming overtly sexual too early can easily come across as crass and off-putting. Remember, the goal is charm, not smarminess. Build attraction and rapport first before venturing into more suggestive territory. There’s plenty of time to explore that later, if the connection progresses.
DO Playfully Tease Her (The Right Way)
Playful teasing can be incredibly effective in creating flirty sparks over text. Think of it like the classic schoolyard crush scenario where someone might playfully tease the person they like.
The key is to tease about light, inconsequential topics that she’s unlikely to be sensitive about. Good examples are her favorite foods, movies, or hobbies. For instance, you could say something like, “Wait, your all-time favorite movie is ‘Pirates of the Caribbean’? I was really starting to like you until you confessed that 😉”
However, it’s crucial to NEVER tease her about potential insecurities or sensitive topics such as her weight, appearance, or pets. Teasing about these things will almost certainly backfire and kill the vibe. One of my clients once jokingly compared his date’s dog to a rat, and it completely derailed the date. Stick to light, surface-level topics for your playful banter.
DO Leverage Photos to Your Advantage
They say a picture is worth a thousand words, and in the realm of text flirting, a well-chosen flirty picture can be more impactful than a lengthy text message.
Sending a compelling photo that subtly showcases your personality or interests – perhaps highlighting your favorite tattoo, a stylish outfit you’re wearing, or an interesting place you’re visiting – can make a significant impression. A woman I used to date would sometimes send me selfies with captions like, “Just thought I’d let you know, I’m looking like a snack today,” and honestly, I couldn’t stop thinking about her for the rest of the day.
Using photos strategically in your text flirting can add visual interest and help her feel more connected to you beyond just words.
Confident man leaning against a brick wall
Alt text: A stylish man confidently leans against a brick wall in an urban setting, showcasing a relaxed yet attractive demeanor, ideal for illustrating confidence in dating advice.
DON’T Neglect Emojis – They Are Your Flirting Allies
Text messages can sometimes lack tone and be misinterpreted. This is where emojis come to the rescue! They are incredibly useful for adding nuance and ensuring your messages are perceived as flirty rather than just friendly.
The right emoji can inject the lighthearted, playful tone you want into your flirty text messages. A simple wink 😉, heart eyes 😍, or the surprisingly versatile upside-down smiley face 🙃 can transform a message from neutral to flirty.
As a general guideline, avoid overdoing it with emojis. Using more than two emojis per message might make you seem overly enthusiastic or even a bit immature. Use them judiciously to enhance your message, not to overwhelm it.
DO Utilize Audio Messages to Add Intimacy
Don’t limit yourself to just text messages. Take advantage of your phone or messaging app’s audio message feature and send voice notes. There are few things more intimate than hearing the voice of someone you’re interested in. Hearing your voice can significantly amplify romantic tension and create a more personal connection compared to text alone.
A couple of tips for using audio messages effectively: Firstly, keep your audio notes concise – ideally under 60 seconds. You want to sound engaging and intriguing, not like you’re rambling. Less is definitely more in this context.
Secondly, strive to sound as natural and relaxed as possible. If you feel a bit self-conscious, practice by sending a “test” audio message to a friend about something mundane, just to loosen up and get comfortable with hearing your own voice. Then, carry that relaxed and natural tone over when you send audio messages to your crush.
Sending a voice note projects self-confidence, and confidence is undeniably attractive. It shows you’re comfortable being yourself and stepping outside the typical text-only communication, which can be very appealing.
By incorporating these dos and don’ts into your text flirting strategy, you’ll be well-equipped to turn those initial online matches into exciting real-world dates. Remember to be clear, engaging, playful, and confident, and you’ll be well on your way to mastering the art of text flirting.
This article is adapted from dating coach Connell Barrett. For more dating advice and tips on building confidence, visit DatingTransformation.com.
