It’s a match! Congratulations on making it through the gauntlet of photo selection, profile writing, swiping, superliking, and first impressions.
The next step is even harder, but with clear communication, a system, and good follow-through, you can avoid what I call “The Texting Trap” to get off the app and on to the fun part of dating…actually having a date!
As you’re deciding when to move off the app, pay careful attention because if you fumble this step, it’s back to square one searching for new matches. This Step-by-Step Decision Guide will help you know which move to make next and keep the crucial momentum needed to be successful off the dating apps.
I’ve also packed the guide with plenty of done-for-you lines you can use, so you’ll always know exactly what to say.
Step 1: Brainstorm Potential Date Ideas
Daters have so many things vying for their attention on their phones. And women especially have a lot of options. That means you have to come up with an enticing date idea to cut through the noise and tempt that cutie to get off the app.
First, timing is everything. Keep the messaging momentum going and ask her out when you’re in the thick of a conversation (i.e., getting quick responses). Don’t pop in out of the blue when you haven’t texted her in days or weeks.
If you’ve been slow to respond over text, most women will assume you’re not assertive or lack genuine interest.
Your date idea should be specific to the person you’re talking to.
Are you someone who takes a spray-and-pray approach to swiping? Do you say the same lines each time? Do you have canned date activities you do with everybody? Wrong move.
Women are well aware of this strategy, and it gives them the ick. It makes your matches feel unimportant and sows disappointment in dating overall.
Instead, be more strategic about your matches. If you are on an app like Hinge or Match, where personality traits shine, you should find plenty of hobbies and interests that you can latch onto for a first date idea that’s specific to her tastes.
The Texting Strategy I Recommend
I have two effective texting strategies that help online relationships quickly translate to IRL dates:
- Comment + Question – This makes your match feel seen and special. Comment on something that stood out to you in their profile. Not something physical like, “you’re beautiful,” but something unique. Then ask a follow-up question and tie it into a date activity. Ex: “I’ve never tried salsa dancing, but I’d be game. Where do you go when you feel like dancing?”
- Gamify – You can pose a nonthreatening This or That question like, “I have to know, are you a coffee or a tea person?” Then suggest meeting at a coffee place or tea house nearby.
Important: None of these messages should be suggestive in the least. No comments about their body, no intimations of being physical, no provocative questions that you think pique their interest. These make you seem creepy and will often lead to an immediate unmatch and block (and possibly even reporting you to the app, which will really set you back).
Your job out of the gate is to make your potential date feel safe and comfortable with you. Trust me, she knows at some point you’d like to be physical with her.
Saying it too soon makes it seem like that’s all you’re interested in. It backs any budding relationship into a corner. She’s not going to say yes to a date if you make her feel pressured to be physical.
Common Messaging Mistakes Men Make
That brings me to some common mistakes to avoid if you want her to agree to see you in person. In addition to trying to be seductive too soon, common mistakes I see are:
- Not ending with a question – You have to think of the chat like a game of tennis and send the ball back after she asks you something.
- Complaining about dating – No one wants to hear you complain about how much you hate the apps, how long you’ve been on them, or how disappointing your last match was.
- Slow-texting – If you take too long to reply, she might lose interest.
- Double-texting – If she’s slow-texting you or failed to respond to your last message, don’t chase. Don’t demand a reply. Make one callback referencing something you discussed before or saw in her profile to get the conversation back on track. Repeat messages can make you seem too thirsty.
Men in the online dating scene face a lot of competition, so even little mistakes can lead to a woman moving on to another match.
Step 2: Take Action & Avoid Time Wasters
The talking stage is an inevitable phase of dating now. Just make sure you’re not slipping into the Texting Trap, in which you build a textationship with someone for weeks or months before meeting.
That builds the Fairy Tale fantasy, which only sets you both up for disappointment when you find that the reality can’t live up to the fantasy.
My advice: Don’t wait longer than a week to get off the app and onto a real date. If someone is dragging their feet and avoiding meeting in person, move on from that match.
How Long Should You Message Before Setting Up a Date?
Follow my 1-to-1 Rule: Move to the next phase, whether that’s a phone call, video chat, or in-person date, somewhere between one day and one week from the time you match.
Same-day connections are usually short-term, so plan at least one day ahead…but no more than a week. That’s the sweet spot.
If you take longer than a week to meet, you’re either going to live in Fairy Tale Fantasyland for too long, one of you will flake, or you’re going to cover all the topics that would have fueled a great first date over text, and your first meeting will feel boring and tired.
Should You Just Come Out With It & Suggest a Date?
That depends on how much trust you’ve built in the chat. I find that my most successful clients have a step between the chat and the date to assess for compatibility and comfort. A simple way to suggest a call is to say:
“I’m really enjoying messaging with you. Would you be up for a call or Facetime to continue the conversation?”
Don’t beat around the bush and hope she’s ask you out. By and large, women still expect men to make that first move.
Look for Red Flags & Don’t Hesitate to Block
Alert! This is the phase where you need to scan for scammers. Fake profiles, bots, and scams have always been a part of dating apps (and online life in general). The real dating skill today is being able to sort out the catfish before you get in too deep.
Ask specific questions that they could not have canned responses for. Ask follow-up questions about things in their profile and make sure their stories line up.
And if they’re putting off meeting in person or even doing a video call, don’t keep hanging in there. Move on. Not meeting in person is a big red flag that they’re either not serious…or not real.
Research out of Harvard shows that people who ask follow-up questions are more likeable, so this will position you well if she’s the real deal. And it will illuminate inconsistencies if she’s fake.
My Dating Safety Reminder: If your match tries to move you to another messaging platform (like Signal, WhatsApp, or Snapchat) or asks you for money or an OnlyFans follow, this is not your soulmate.
Step 3: The Call
Now, I know many people skip this step. Some matches will tell you they don’t want to waste time on a call. However, both of you will end up wasting more time meeting up if it’s not actually a fit.
If you suggest a call, and they resist, never make it about you wanting to see if they are the real deal. Don’t act like it’s a rigid rule you have for dating. Instead, make it about helping them.
Say, “I wouldn’t want to waste your time” or “I think it’ll help us get to know each other.”
If they still say no, you have to decide if you’re comfortable proceeding with an IRL date. Whatever you do, don’t simply switch from the app to text to keep the conversation going.
There’s a common misconception that if you exchange numbers, that’s a step forward. Old-fashioned pickup artist thinking trained many men that the goal is to get the girl’s number. But that’s a dead end. If you exchange numbers, it has to be with a specific plan to move the relationship forward.
This looks like: Can I call you tomorrow after work?
Not like: Here’s my number, text or call anytime.
The first sets you up to be the hero when you actually call when you say you will. The second sets you up to never hear from her again as she waits for you to make the first move.
If you do call or video chat, keep it short and sweet. Just enough to make sure that you have enough curiosity about one another to sustain the first date. In other words, about 15-20 minutes.
At the end of the call, you can easily move the ball forward on the call by saying, “I’m really feeling a connection with you. Why don’t we meet up in person?”
Otherwise, keep your conversation within the app until you actually set up a date. Only exchange numbers for date contingencies.
Step 4: Setting the Date
This step is where many men mess it up. You likely have one voice in your head saying, “Don’t come on too strong!” and another voice saying, “How do I separate myself from all the other men in her DMs?” and that keeps a lot of men paralyzed in a state of inaction.
The best way to stand out from the other matches that you assume she’s making (and I assure you, it’s not usually as many as you think) is by taking the lead, being decisive and clear, and going for it.
Specificity is king. Instead of “We should get together sometime.” Try a more direct approach: “When are you free this weekend?”
Or a playful approach: “Let’s get tacos! Is this Tuesday too cliché?”
Whichever strategy you use, keep your goal in mind: Get on her calendar with a specific plan. The invites that are a vague version of “let’s see each other sometime” are the ones that get forgotten or canceled when something more exciting comes along.
Make a plan and follow through, and you’ll rise above all of the time-wasters and incessant chatters taking up precious real estate in her inbox.
When you do make that specific date ask, consider how far she has to travel to the location and ideally select a spot that is closer to the location she’ll be coming from.
Most women no longer want to be picked up for a date for safety reasons, but you can always offer to send her an Uber if you sense that she’s yearning for chivalry.
How to Overcome Fear of Rejection
She might say no. But she will always respect a direct ask, and it’s better for you to clear your roster if you have unserious options pulling focus from people who actually want to meet you.
Getting clarity is the fastest way to move in the right direction in the dating world. Don’t let one rejection get you down. Keep matching until you get the yes you’re looking for.
What If She Says No to Meeting But Wants to Continue the Conversation?
The next step here depends on whether it was a no to a specific time or date idea or a no to dating you entirely. You don’t need a dating app pen pal.
You might be chatting with someone who is shy and needs time to trust you. You’ll need to decide if you’re making an investment or getting strung along by someone who is in it for different reasons.
Don’t Stay Online Forever! Put Yourself Out There
Our society has conditioned us to pursue low-effort asks and protection from rejection, but neither of those things helps you grow or helps you show that you’re the knight in shining armor your princess has been waiting for all along.
Remember that the point of dating apps is to make real connections. It can feel good to match or message with a beautiful woman, but if she’s not willing or able to move off the app, you’re just blocking yourself from meeting someone who will.
