Texting can be notorious for accidental misunderstandings. When you’re texting, you’re missing the added context of body language, tonality, and facial expressions. Emojis can only tell you so much about how the person is really feeling.
Check out this example from a simple English language exercise on how what word you stress completely changes the sentence’s meaning.
- I didn’t say he stole the money: Someone else said it, not me.
- I didn’t say he stole the money: I am explicitly denying that I ever said it.
- I didn’t say he stole the money: I might have implied or thought it, but I never spoke the words.
- I didn’t say he stole the money: Someone else took it, not him.
- I didn’t say he stole the money: He might have borrowed it or had a right to it, but he didn’t steal it.
- I didn’t say he stole the money: He stole some money, but not this specific amount or stash.
- I didn’t say he stole the money: He stole something else entirely, like a car.
Texting is one of the main ways we communicate now, so you’ve got to be on your game to move a romantic interest into the real world.
Here are my tips for keeping texting fun, clear, and flirty…without coming off as a total creep.
Match Her Energy
Get ‘em interested by being their type of guy.
Mirroring is a good technique to start out a text conversation. If they’re sending short texts, respond with short texts.
Make sure to match their energy, text length, and style. If they write three words, don’t write a big paragraph. If they like emojis, use emojis.
Don’t jump too quickly into flirting (unless they initiate that sort of thing). First, get into a friendly conversation, then get into flirting.
This can be the difference of two to three texts. You don’t want to start off at full speed.
Give Compliments
Compliments are good, but most guys compliment wrong. They make it about physical attraction rather than a deeper connection.
My pro tip: Compliment her choices. Say nothing about her looks.
For instance, “Just saw that you ski! That’s impressive!” or “Good call on U of Nebraska. It’s a great school.”
Why this works: Many of the compliments that women get are about their bodies, so complimenting them on something else will immediately help you stand out.
Ask Questions
Then toss out an easy-to-answer question to break the ice. Mention something that references her profile prompts or photos. That’ll make getting a response more likely.
Here are some examples:
- What’s your favorite place to ski?
- What was the best football game you went to?
- What local burger places do you recommend?
Keep the questions open-ended, meaning she’ll need to send more than just a yes or no answer. Ask her about her experiences, her opinions, or her plans for the future.
Flirt Without Crossing Boundaries
Start the flirting slowly. More of a wink than a nudge. One of the ways to start flirting a little is to tease her. Now I know we talked about things being misinterpreted, so make it clear you’re joking around and not taking it too seriously.
When you tease, you’re bringing an element of excitement to the chat. You’re showing you’re willing to take a risk. But choose something very low-key to tease about (i.e., no teasing about her religion, looks, or family life).
Find a little detail about her and use it to create a playful jibe:
- “If you ski, please tell me you’re not one of those little ‘snow bunnies’ in branded pink skiwear that just do the bunny slope.”
- “Since you went to Nebraska, I’m assuming you’re still a little salty about when (insert viral team here) beat you guys?”
This does not mean “negging” her and throwing out a subtle insult. That’s manipulative and has a high risk of leading to your being blocked.
The goal isn’t to put her off, but to see how she responds to a little playful banter.
Know When to Move Offline
Okay, you’ve had some good texting back and forth. Now it’s time to propose the date. Get to meeting in person. Lock it in.
There are a few ways to do this, depending on the context and your comfort level.
The Direct Approach
After you say something funny and she reacts well. “I’ve enjoyed this! Let’s meet in person and continue getting to know each other.”

Remember that statements are stronger than questions in this approach. It shows confidence, and that’s attractive.
A Playful Ask
After she says something funny, you can say something like: “You are too funny! Are you this funny in person?” And then hope that she rises to the bait.
This text is more of a hint than an invite, so you can take the temperature of the match before prodding a real plan forward.
An Open Invite
Let her know where you will be and what you’ll be doing. Say that it’d be better with her. “This weekend there’s an arts festival that’s really fun. My friends and I are going and would love to see you there.”
This takes a lot of confidence and trust in the match. It puts the ball in her court without a lot of overt pressure. Because you’ll be there having fun either way.
FAQs: What Do I Text After the First Date?
Great! You had your first date. Let’s assume it went well. Well enough that you’re still texting, at least. Now we want to raise the flirting and fun level.
If you want to text that night after seeing her, you could say:
- “Had so much fun… my mind is whirling with ideas for a second date.”
- “Hi, just wanted to check to see that you got home safely. Thinking of you.”
If you want to compliment her, be specific. I recommend using two sentences to demonstrate you paid attention and put thought into it.
- “That dress you wore was beautiful. The little jewels in it kept catching the light all night,”
- “Great choice on that restaurant! Honestly never thought I’d like pink salt and smelt!”
You’re not being overly emotive, and you’re not asking her anything. Instead you’re showing interest in her and leaving it open if she wants to respond.
How Often Should You Text Someone You Like?
At least once a day is generally a good pace for when you’re getting to know someone. But there are always exceptions to every rule. Some singles are very busy and can’t keep up with daily texting. Be clear with your text buddy if that’s the case, and try to be as consistent as you can.
If you want the connection to flourish, you should aim to answer her messages within a few hours rather than a few days. You want to create a steady, reliable back-and-forth. Disappearing on her will break the spell.
have been ghosted.
Tech companies know we get a dopamine rush when we get that notification on our phone of “new message.” When that dopamine gets attached to you, that can help build attraction. So you want each text to be timely and pack a small, good punch.
Is Double Texting Ever OK?
I say it’s fine. We’re all adults. If you want to text her again, text her again. Maybe don’t triple text without getting a response back first…but showing interest in the dating world is not a bad thing. Just be polite and conscientious of her time.
Don’t take her silence as an insult. She might simply be busy or dealing with some issues that have nothing to do with her attraction to you.
When Is It OK to Text About Sex?
Okay, yes, after a bit of small talk and polite conversation, we can get suggestive and sexual with our texting, and it can be a lot of fun! BUT if you do it wrong, you could crash and burn miserably.
Start being slightly suggestive in your language to feel things out. Get her to think of you naked without being graphic or sending creepy photos. I like to use a subtle mention of a shower like this:
“Looking forward to tonight! Going to jump in the shower and see you there in about an hour.”
You are not making a big deal out of you taking your clothes off, but nonetheless, you’re dropping the image there.

You can talk about clothing-optional activities as well. “I liked summers on a lake in my college days. Bonfires, skinny dipping, smores, bad guitar.” Again, you’re not drawing attention to that one part, but it’s noticed.
Being suggestive is not just about wink, wink, nudge, nudge, it’s about getting her mind to suggest things. If she's vibing with you, she'll pick up on it.
You can also send her a picture of your perfectly made bed (women love headboards!) and say something like, “Ah, nothing like a freshly made bed. Be a shame if something were to happen to it causing all the sheets to be ripped away.”
And let her own mind suggest what could possibly cause that to happen.
How Do You Know If Someone Enjoys Texting You?
If you're unsure if she is enjoying your vibe, pay attention to some of the following. If any of these are happening, you may want to dial it back a bit.
- She’s not asking you any questions.
- She doesn’t acknowledge the flirting.
- Her response times are getting longer and longer.
- She’s only giving one-word answers.
- She changes the subject when you suggest meeting.
It doesn’t mean it’s over, but it may mean it’s time to focus on other conversations and not put all your hopes in this basket.
Try sending a last-ditch invite: “Hey, if you’re interested in meeting in person, let me know. You seem really cool, and I’d love to hear more about your [insert hobby/interest here].”
Text Deliberately & Thoughtfully to Demonstrate Your Good Qualities
Many times, we meet someone interesting online and only later get to meet in person. If you think the person is fun and pretty and you want to meet them in real life, you have to text consistently and politely in a way that gets them interested in texting you back.
You can start to earn trust early by simply being true to your word. At the beginning, she doesn’t have much to go on except what you say.
So you can start building trust by telling her you are going to do something and then do it. She mentions something she’s interested in or something cool that’s happening soon, you can say to her, “That sounds cool, I’m going to look up some more info on that and will text my thoughts tomorrow.”
You’ve made a simple pledge, so do it. Take a minute or two and look it up. That’s easy enough to do. Now, what you’ve also done is create anticipation. You said you’d text her back tomorrow, but not when exactly.
So she’ll be wondering, firstly, if you’ll be texting her and secondly, if you do, when? When you text her back at 3:00 pm, you’ve kept your word, built trust, and helped create some fun anticipation.
Attraction is all about that subtle pull of intrigue. Give her a reason to want to text you or be excited to hear from you. Be consistently kind and positive. And a bit flirty. Follow her lead when it comes to escalating the sexy talk, and you’ll do just fine.
