Here’s a common scenario I see with my clients who are online dating: they matched with someone on a dating app, spent a few weeks messaging but have yet to meet. They start to wonder, “Am I actually making progress, or am I just wasting my time?” 

Have you been in this situation?

It seemed like a good match at first. Your profiles aligned, and all the messaging seems promising. The banter is fun and messages are frequent, personal, maybe even intimate.

At this point, it feels like maybe you are in a relationship with this person. But without meeting in-person, it’s hard to know anything about this person you are messaging for sure.

What if when you eventually meet, there’s no spark? 

What if this person doesn’t actually look or act like their online persona?

What if this person has been dating others and is just keeping you on the back burner? 

What if this match is not actually a real person? Or worse, did you become emotionally attached to a scammer?

Did you just invest your weeks (or months) worth of time, energy, and emotions for nothing? And how do you avoid this in the future?

Of course you don’t want to go on a real date with every person you  match with. And if you don’t live near each other, how can you move the relationship along without meeting in person?

How much messaging is too much? How much is too little? It’s enough to drive yourself mad!

In order to make sure you aren’t wasting time or getting scammed, here are four messaging scenarios to be aware of and how to ask for the meet up!

Scenario #1: The Endless Pen Pal

This is the person that just chats you up without committing to anything that moves the connection forward. In all likelihood, this probably isn’t a malicious situation. 

Maybe they just like having someone to talk to. Maybe they’re insecure and don’t know what to do next. They could be new to dating or online dating and just don’t know how to proceed. 

What To Do: 

Regardless of their reasons, if you don’t want to be pen pals, you need to kindly express your expectations.

If you seem to be connecting well within the first week of messaging, try something like, “I feel like we get along and I’d love to have a video date sometime soon so we can both see if this connection has potential”.  

This first “visual encounter” should be online through the dating apps video messaging or a site like  Zoom. That way you can see if there is a flow or if something seems off.

If they push back, or seem hesitant, follow it up with something more direct.

“I’m looking for a real life relationship, and I’ll only be messaging with someone for a couple of weeks max.  After that I expect to meet via video chat to see if we want to then meet in person.  Are you up for that?”

If the person doesn’t step up, then I recommend you block them and move on. 

Scenario #2: The Casual Dater/Manipulator

This person isn’t interested in anything serious and/or may be in one or more relationships. This includes potentially being married or committed to someone in real life. 

Unfortunately the casual dater, even an unattached one, may not be honest about not wanting a serious relationship. I find this to be more true of men than women, but it can go both ways. 

He knows that you are looking for something serious, but he doesn’t want to lose the ego boost your messaging provides so he says all the right things to string you along, including agreeing to meet up, when he has no intention of following through.

This person will come up with all sorts of reasons why they’re unable to meet “right now”.  “I’m traveling”, “I’m taking care of my family”, “crazy work schedule”. 

What To Do: 

Again, the response is to stick to your guns and be clear about your expectations. 

“I completely understand about being busy. If we can’t get together sometime in the next week, then let’s put things on hold until you have more time to pursue a relationship. If I am still available, we can go from there.” 

This makes it clear that you are expecting a relationship to progress and that you aren’t going to be waiting around for them. 

The manipulator may actually take you up on a meeting, just to keep you hooked. But after an initial meet-up they will likely make excuses again why they can’t meet more frequently. 

Especially watch out if they refuse to meet in public, avoid any normal details about their real life, keep you hidden from their world after you have met, or consistently avoid taking reasonable steps toward a real relationship.

Scenario #3: The Catfish, AI Bot, or Scammer

This “person” has malicious intent and they are looking to scam you in some way. They are never what they seem. 

Someone with malicious intent will try to quickly move the conversations outside of the dating platform, but never to anything in-person. 

It may feel like progress when they give you a “real” phone number for texting or moving the conversation to WhatsApp. In reality they are trying to get you outside of any protective security that is part of the online dating platform. 

Depending on their end-game, their messages may become deeply personal long before any discussion of meeting.

They’ll try to strengthen the connection with personal stories and details that draw you in. They are hoping to get the same kind of information from you that they can use against you later.

They may ask you personal questions, begin love-bombing you, fake a personal tragedy, or send you links to cam-sites or malicious apps, sometimes with the guise of “meeting”.

What To Do: 

NEVER click on a link that a stranger sends you. Even if it’s to “connect”. Until you meet in real life, this “person” is a stranger! 

Worse yet, they may not even be an actual person! AI is making it incredibly difficult to know the difference between a human and non-human interaction. Even in video

According to Prevent AI Scams, the best way to know if someone you are chatting with is actually AI is to:

“request a live video call and ask them to perform a specific action in real time(hold up a word you choose at that moment). Beyond video: ask questions that require genuine personal memory or sensory experience. Watch for too-perfect emotional consistency— AI never gets tired, distracted, or irritable, and that inhuman consistency is its own tell.“

Also, you should be the one to set the time and platform for the first video meet-up. Do not use your phone number for messaging or a video call, even if they ask. 

If your dating app doesn’t have a video chat option, Zoom is a free and safe way to connect without giving out personal information.

Scenario #4: The Long-Distance Relationship. 

Navigating online long-distance relationships is its own adventure, but I have many clients who have done this successfully. Don’t rule out that true, lasting love may be a state or even a country away. 

Obviously, this means more messaging and less in-person meetings, however you can still enjoy online video correspondence.

What To Do: 

Yes, meeting up for coffee is out of the question (for now), however most dating apps have video chatting options. So, Just like with every other situation, try to initiate a video call within the first couple of weeks.

Once you have established that they’re a real live human being who looks and acts like their profile and messages, you can relax a little and continue getting to know them better.

Long-distance dating can work, but both people must be willing to verify who they are, communicate consistently, and make a realistic plan to meet.

So how long should you message before meeting someone from a dating app?  

If the messaging is frequent and you are beginning to think there is something worth pursuing, don’t go longer than a couple of weeks. 

Before you over-invest, keep these guidelines in mind:

1. Suggest a next step within the first couple of weeks.
   If the conversation is frequent and there seems to be genuine interest, suggest a short phone call, video chat, or casual in-person meeting.
2. Keep the first meeting short, simple, and public.
   Coffee, lunch, or a daytime meet-up in a public place is usually best. Drive yourself and let someone you trust know where you’ll be. The goal is not a romantic date, but rather to see if there is real-life connection.
3. Stay on the dating app until basic trust is established.
   Don’t rush to give out your phone number, personal email, address, workplace, or social media before you know the person is real and trustworthy. I recommend to my clients to get a “Google” number that masks your actual phone number.
4. Never click links from someone you have not met.
   Be cautious of links to “connect,” “verify,” “watch,” “vote,” “invest,” download an app, or view photos somewhere else.
5. Do not send money, gift cards, financial help, or sensitive personal information.
   No matter how convincing the story sounds, this is one of the clearest scam warnings.
6. Be careful with love-bombing and instant intimacy.
   Big declarations, intense future talk, or “I’ve never felt this way before” language before you have met can be a manipulation tactic to create an emotional attachment.
7. Trust patterns more than promises.
   If someone repeatedly avoids a call, video chat, or meeting, pay attention! A seriously searching person will usually try to move the connection forward, not slow it down.
   

The bottom line is that messaging should help you decide whether to take the next step and meet in person. It should not become a relationship in itself. 

A seriously searching person may not move at lightning speed, and that’s okay. But they should be willing to move from messaging to meeting with clarity, consistency, and respect.  

If you’re still unsure how to proceed or need help navigating online dating, reach out and let’s talk.

Schedule a complimentary Meet Your Mate Strategy Session with me, and let’s get you from chatting to cherishing lasting love!

About the Author

is a certified life coach and dating/relationship expert who has helped hundreds of marriage-minded singles find lasting, committed partnerships since 2005. Through private coaching and group programs, she specializes in helping people date with clarity, confidence, and purpose.