Men appreciate processes. Leaning into the logical side of our brain, we look for fixes and understandable pathways. That can be great for engineering, but it doesn’t quite work so well with human emotions.
Logic doesn’t always align with falling in love. For those who may not consider themselves to have a high emotional intelligence, navigating the world of dating and flirting can seem downright confusing.
Now, while each case and each person and each relationship is different, there are some “most likely” scenarios that can help you with early dating interactions.
Let’s go through some tips, scripts, and timelines in online messaging and dig into the “why” of the best practices when going from first message to first date.
Day 1: Send a First Message That Gets a Reply
It’s Thursday and you’re doomscrolling on the couch when you can’t take it anymore. You hop over to the apps and BOOM, there she is.
Your mouth drops a little and your eyes widen as you read about her. “I have to meet her,” you think to yourself.
You open a chat window and feel stuck. What do you write?
Well first off, don’t mention her looks or anything identifying about her. If she has red hair, do NOT lead with that, ever. She has heard it all and is sick of it.
Guys often think (wrongly) that a compliment will flatter her into agreeing to a date. But most single women get numb to such compliments pretty quickly after creating a dating profile because they’re seeing generic lines all the time.
She’ll know you think she’s attractive… because you messaged her.
Instead of focusing on the physical, mention something that caught your eye in her profile. Does she have a good sense of humor or an interesting photo? Do you like the same food?
Look for a commonality, and then ask an easy-to-answer question. Don’t overthink it!
Here’s a simple example:
“Hey there, I see you’re a skier, that’s cool! I used to ski but haven’t in a while. Where’s your favorite place to ski?”
If there’s one truism about online dating it’s that attractive girls get LOTS of unsolicited messages. Every day, their inbox is blowing up. So make your message light and easy to respond to.
Keep things positive. Hopefully you trigger a happy memory, which she may start attaching to thoughts of you.
Don’t write more than three sentences. And one of those sentences had better be a question!
Days 1-2: Establish Early Rapport
OK. She responds.
Cue the marching band, huzzah!
…now what?
Well, to use a fishing analogy, you’ve got a bite, now you want to reel her in!
You want to make your messages fun and interesting while making it easy for her to respond. This is where you start building that connection.
Let me make a point here, real quick. Don’t fall for all that “wait-three-days-to-text-her” or playing hard to get whatnot. Big mistake!
If you like her, don’t play games. Respond normally, not obsessively, and if you’re going to err, err on the side of letting her know how you feel, not playing it cool and leaving her wondering if the spark is there.
Let’s say she answered your message like this:
“Hey there! Yeah, I grew up in the North Country, so you had to get a winter sport or go crazy, lol. I like skiing in Vermont, Okemo, or Killington. How about you?”
So first, how did receiving this message make you feel? Let her know that!
“So great to hear from you!”
Then, acknowledge what she wrote to you.
“I have skied Killington before but have never been to Okemo…”
Add a little something to show her that her opinion matters to you.
“…I’ll have to check it out sometime.”
Answer her question with a little “question bait.”
“In North America, my favorite place is Park City.” Don’t you immediately want to know where else this person has skied?!?!
Then, like tennis, you want to lob an easy-to-answer question back at her to keep the energy going.
“Do you have any place you’d love to go skiing but haven’t yet?” This can lead into travel questions and let you in on something that’s on her wish list.
This early part doesn’t have to get too deep. You’re taking turns sharing little tidbits about yourselves and proving you can hold a polite conversation.
Days 3-5: Keep the Momentum Going
This is where you’re building good energy and positive thoughts. This stage can vary a lot depending on personalities.
If two people are super communicators or have jobs that allow them a lot of downtime, it may look like multiple messages back and forth a day. They can keep up lightning-fast response time and constant communication. Busy professionals may only check in once at the end of their workday.
There’s no set way to do it, though I’d suggest trying to mirror the other person. If she writes two sentences, you should write two sentences back. If she communicates through memes, send her some memes!
Side quest: This is also the window of time that you can ask to move the chat off the app and exchange phone numbers.
What you DON’T want to do is overshare too quickly. You don’t have any sort of foundation yet, so it can be easy to accidentally destabilize the connection.
For this example, let’s say you’re exchanging two messages each per day for three days.
Day 3
“I’d love to go skiing in the Italian Alps someday. Have you ever been there?”
“I haven’t but would definitely be up for it. I was lucky enough to go skiing in Chile a few years back, which was cool. Any fun places you’ve been recently?”
“That’s so cool! I’ve always wanted to visit South America. It sounds silly, but I did a report on Ecuador in elementary school and have wanted to visit since. What brought you there?
I went on a safari in Kenya a few years ago! It was incredible.”
“So we had an exchange student stay with us in high school, and he just got married, so we flew down for his wedding. I hadn’t been to South America before. I liked it and would go back.
OMG, I’ve always wanted to go on a safari!!! What was your favorite part?”
Day 4
“Loved seeing the lions. I had no idea how big they are in real life!”
“That’s awesome! I’d love to see some pics of that trip, can you send me your number/snap/IG/whatever? I’ll show you some fun ones from Chile.”
(This gives you a REASON to get off the app.)
“Sure, my info is _____________. Looking forward to seeing the pics.”
“Here are my 3 fave pics. Me on a burro in the Andes, freaking penguins down near Valparaiso, and the biggest meat platter I’ve ever seen. Ask me if we finished it…”
“Love these! I’ll send you some when I get home from work.”
Day 5
“Sorry I didn’t send the pics last night, I got home late and crashed. Here are a few of the lions, and here’s me on an elephant!”
(Now is a good time to reply with a voice note. Let her hear your voice and it shows your desire to “up” the communication.)
“That’s so cool, definitely on my bucket list. I’m walking to my car and just thought I’d drop a voice note so you can tell I’m real! I would love to hear more about your safari. Have a great one and can’t wait to hear your voice!”
(You’re asking her to mirror you and send you one as well.)
“So great to hear your voice, now you can hear me too! One thing nobody mentioned to me is apparently Latina blood is like a delicacy to the mosquitoes over there. So. Many. Bites. Hahaha. Anything attack you in Chile?”
“Nothing attacked me, but that stupid burro laid in the shade and refused to move for like 20 minutes even though the guide was yelling at him. Don’t speak much Spanish, but I definitely caught a few words I remember from my days working in kitchens!”
“OMG, too funny, I can probably teach you some more words, haha!”
As you can see, ending with a question is a must, and it helps to provide specific details the other person can respond to. And if things are lining up well, you can try to get a bit deeper with the messages.
Day 6: Ask Her Out on a Date
Okay, you like her, you guys seem to be vibing, time to shoot your shot! Before you ask for a date, you need to have developed some kind of rapport. If you guys really messaged a lot, you can probably ask for a date sooner rather than later.
But within about a week you want to know if this person is serious about dating and not just looking for a pen pal or ego boost, so now’s the time to ask.
Even if you haven’t moved off the app yet, it’s okay to ask for a date. You need to know if you are wasting your time or not.
So whatever medium it is, you want to 1) remind them again how you feel 2) tell them you want more 3) propose an idea.
“I’ve been having so much fun talking to you and your voice is so cute! I would love to hear it face-to-face. This weekend is supposed to be nice weather. Want to grab a coffee or something and go to the park?”
If she can’t make it, but the conversation keeps flowing, you can try again a few days later.
If you are serious about dating, you want to make sure your energy is going in the right direction. If she won’t commit to meeting or facetiming or calling, then you have your answer on how much effort she wants to put in.
Day of Your First Date: Locking It In & Confirming
Don’t overthink it, and don’t offer them an out. “Hey if you can’t make it…” No.
“Are you still down…” Never.
The night or day beforehand you can send a quick confirmation text: “Can’t wait to see you tomorrow! Should I order something for you if I’m first?”
You’re confirming for you and offering something kind.
Here are some more examples:
“Excited to hear your travel stories. We said 4 PM, right?”
“I’m walking my dog, and then I’ll be on my way. See you soon!”
“Such a beautiful day! I’ll be wearing my red shir,t so I’ll be easy to find. Do you want to sit inside or outside?”
These messages are upbeat, confident, and affirming. You’re letting her know you’re in and not flaking on her. She should respond similarly.
The Core Rule to Remember: Momentum Is Everything
Keeping momentum is the most important thing here. If you let the text message sit unanswered for too long a period (even a few hours could be bad for high-volume texters), it sends the signal to the person that you don’t care or are too busy for a romantic relationship.
You don’t have to send the perfect message. You just have to keep the conversation flowing and build enough of a rapport that you can confidently ask, “Are you free this weekend?”
Take it one step at a time, and keep in mind that you don’t have to be the wittiest texter on the planet. You just have to be present and show honest interest in her. Good luck out there!
