A good friend of mine is charming and charismatic in person. I’ve watched him meet random women, work his magic, and walk away with their phone numbers and more on many occasions. However, he rarely hung out with these women again. When I asked why, he had no clue. He would text them, but, after a few days, the conversation would just die.
He was frustrated after one especially attractive woman stopped messaging him. He shoved his phone in my face and asked what he was doing wrong. It wasn’t difficult to see his mistakes.
She was trying her best to engage him, but he responded with one or two word answers. When she tried to get fun and flirty, he replied with businesslike answers. This fun, exciting guy was bland and boring when he messaged.
He didn’t understand how to entertain a girl over text or even that it was so important. He took an old fashioned view of texting: that it was for basic communication. Many guys take that view. Others want to make a girl laugh and flirt over text, but just don’t know how.
Regardless, if you’re wanting to entertain a woman over message, this article will show you how!
Let Your Personality Shine Through
My friend was a charming, charismatic guy who could easily entertain women in person. They loved him! But, once he started texting, all of that ended as he became stiff, robotic, and all business. His problem wasn’t a lack of charm or charisma, but an inability to let that core personality come out over text.
Now’s a good time to take our entertaining and informative “What Is Your Dating/Relationship Texting Style” Quiz. See if your texting style is holding you back!
If you are funny, clever, charming, and a generally cool person, then knowing how to entertain a girl over text is easy: you simply be yourself when in front of an electronic device. Don’t let the screen and the keypad get you into “computer mode” where your interactions become stiff and formal.
Instead, treat text like you would any “real world” interaction. Let yourself have fun and flirt. Make jokes. Be sarcastic and a little edgy. Set a fun and light tone and go with it!
Remember that attractive women get a lot of attention from multiple guys. The girl you’re texting might be getting messages from 10-15 other men. Sure, she might not be interested in all of them. But, they’re still your competition in the sense that they are competing with you for her best attention.
The way to rise above other guys is to not only entertain her, but to be original with what you do. You can best achieve this by being funny in an observational way. This means looking at her life and your relationship with her, then entertaining her based on that.
For example, rather than quoting some comedian, repeating something funny you saw on TV, or telling jokes you got off the internet, make your own humorous original material related to her. Obviously, you can borrow from other people’s humor. Just craft it to her situation and make it your own. This can take the form of telling funny stories about your life, joking around about her stories, crafting funny wordplay, and so on. Check out this resource on observational humor for more tips.
Tease And Flirt
Women love when guys tease them and flirt with them. However, when I say teasing, I’m talking about joking around and giving them a hard time in a fun, flirty manner. I’m not talking about bad-mouthing them or putting them down. If you haven’t established a fun, friendly tone, you must do that before teasing women.
Here are a few topics where you can effectively tease women over text: spelling errors, clothing and hair choice in their selfies, complaints about their day, etc.
For example: if she makes a spelling error, you can say, “There’s no “e” in potato. And here I thought you won the spelling bee in fifth grade.” Or, if she says something like “I yelled at my boss today” you can reply, “Wow, I didn’t know you were so sassy!” If she sends a selfie with a new outfit, you can say, “That’s a cool shirt. It reminds me of my grandma’s curtains.”
You can add emojis for effect here, like a winking smiley (avoid a straight smiley). And, let her know that you’re kidding if there’s any doubt. For example, after joking about her shirt, you can say, “I’m kidding. Of course it looks good on you!”
This gentle teasing is actually a type of flirting. And, if done right and she considers you attractive, she’ll enjoy it.
Draw Her Into Your (Entertaining) Life
Unless you’re simply content randomly entertaining women, your goal learning how to entertain a girl is to get into some kind of relationship with her. So, you definitely want to entertain her in a way that draws her into your world. Even better: have such an entertaining life that she can’t resist you.
Let me give you an example. I do very interesting things: go to concerts regularly, write books, speak in front of large audiences, and have been on the TV and radio. Not only do women find this entertaining and fascinating, but they want to be a part of it, either by dating me or, if they’re taken, by being my friend or associate.
You want to communicate with her over text in a way that shows her what an overall entertaining and exciting life you live. Then, as you’ve shown her how great it is being you, you can invite her to be a part of the next best thing…being with you! If you’re attractive and exciting, no woman will be able to resist that.
If you can’t think of anything fun and entertaining to communicate to her, then it’s a bigger problem. You’re not coming across as entertaining over text because you’re just not a very exciting person. If this is the case, you need to find ways to make your life more fun and exciting. My book Be Popular Now can give you great tips to be more generally exciting, attractive, and popular. Once you’ve achieved that, you can apply these principles to show her over text.