How to Flirt with a Guy Over Text: Best Tips and Examples

September 25, 2021

Introduction: The Art of Digital Romance

In the age of smartphones and social media, texting has become an essential aspect of building relationships. Understanding the importance of texting in today's dating world is crucial for creating meaningful connections.

The Importance of Texting in Today’s Dating World

Texting is not just a way to communicate; it’s an essential tool for flirting, building rapport, and showing interest. It can bridge the gap when you’re apart and enhance the relationship when you’re together.

Setting the Stage

Choosing the Right Time to Text

Timing is everything. It’s best to text him when you know he’s free and can engage in the conversation. Avoid sending messages when he’s likely to be busy, like during work hours.

Starting the Conversation with Confidence

Initiating a conversation shows confidence. Start with something light, such as talking about a shared experience or something that reminds you of him.

Knowing Your Texting Style and Adapting

Everyone has a texting style. Whether you’re witty, humorous, or more direct, let your personality shine through. If needed, adapt your style to the conversation’s flow.

Crafting the Perfect Texts

Strike a Balance Between Playfulness and Sincerity

Using Emojis Wisely

Emojis can add a fun element to the conversation. Use them to enhance your words, but don’t overdo it as it might dilute the message.

Gentle Teasing and Banter

Engage in light teasing and playful banter to create a fun and flirty atmosphere. Make sure it’s mutual and that he’s enjoying it too.

Complimenting without Overdoing It

Genuine Compliments

Tell him what you genuinely like about him. It can be his looks, intelligence, or how he makes you feel. Make sure it’s genuine and from the heart.

Avoiding Common Clichés

Avoid generic compliments. Be specific to make him feel special.

Keeping It Interesting with Open-Ended Questions

Asking About His Interests

Ask about his hobbies, passions, and dreams. This shows you are interested in his life beyond the surface-level conversation.

Creative and Fun Questions

Throw in some unexpected questions to keep the conversation lively. For example, “If you could have a superpower, what would it be?”

Building a Connection

Sharing Bits of Your Life

Personal Stories and Experiences

Share stories that he can relate to or find amusing. This can create deeper connections.

Hobbies and Passions

Talking about what you love shows you have depth and can make you more attractive.

Reacting to His Texts with Enthusiasm

Expressing Genuine Interest

Respond positively and express genuine interest in his stories and achievements.

Offering Support and Encouragement

Be there to offer words of encouragement. This can build trust and show him that you care.

Flirting Techniques

Subtle Flirting – Less is Sometimes More

Using His Name

Use his name in texts. It's personal and gets attention.

The Power of Subtle Touches in Text (e.g. “hugs”)

Expressing a virtual touch like hugs or high-five can create a sense of intimacy.

The Double Entendre – Mastering The Art of Suggestion

Playfully use words with double meanings to flirt subtly.

Navigating the World of Memes and GIFs

Using memes and GIFs can add humor and express emotions in a fun way.

Creative Use of Photos and Snapshots

Sending photos can make the conversation more personal. Make sure they are appropriate and in line with the relationship’s nature.

Gauging and Keeping His Interest

Detecting Signs of Reciprocal Interest

Pay attention to his responses. If they are elaborate and engaging, he is likely interested.

Using Text to Plan Real-Life Encounters

Use texts to make plans to meet up. It’s a great way to move from virtual to real life.

Avoiding Texting Pitfalls


Don’t bombard him with messages. Give him space and let the conversation flow naturally.

Misinterpretations and Miscommunications

The text lacks tone and facial expressions. Be clear in your communication and don’t be afraid to clarify things.

Staying Safe and Setting Boundaries

The Importance of Online Safety

Don’t share too much personal information and be cautious until you know him well and can trust him.

Setting and Respecting Boundaries

Know your limits and make them clear. Respect his boundaries too.

Handling Rejections Gracefully

If things don’t work out, it’s important to handle rejection with grace. Move on positively.

Texting Examples for Inspiration

The Casual Check-In

“Hey [His Name], how’s your day going? 😊”

The Playful Tease

“Is that another dad joke I see? You’re officially the king of them! 😄”

The Thoughtful Message

“I read this article today and it made me think of you. You always have such insightful thoughts on [insert topic they may be interested in].”

The Flirty Challenge

“How about a coffee showdown this Saturday? The loser buys the winner their favorite coffee 😉”

Conclusion: The Ever-Evolving Art of Text Flirting

Flirting over text is an art that evolves with time and relationships. Stay genuine, have fun, and let things progress naturally.

Final Words of Wisdom for the Tech-Savvy Romantic

Embrace the technology but never forget the human behind the screen. The aim is to connect deeply, have fun, and maybe find love in the process.

Remember that texting is like dancing two steps forward, one step back, and believe me, you will end up on a date with this guy. Read our guide on how to make a guy chase you for more information.

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