How to Transition to Actually Go On a Date From a Dating Site

Online dating is awesome. It gives us a fantastic and unique way to meet people that we never would have had the chance to meet otherwise. But, sometimes it can be tough to make the transition from just chatting online with someone to actually going on a date. How do you make that transition? How do you bring it up? When is the right time? What happens if they are hesitant?

These are all awesome questions and ones we hear a lot. In this guide, we’re going to walk you through how to transition to actually go on a date from a dating site. We’ll show you how to take that next crucial step to potentially getting that interaction or relationship to the next level – the first “real” date.

How to Know When the Time is Right

The toughest part of the transition from dating online to a date in real life is knowing when to make the move. The answer is that it’s going to be heavily dependent on a few things.

The Type of Match You’re Chatting With

First, it’s going to depend on the person that you’re talking with. Some people really like to get to know people well before they commit the time to meet them in person. This can be because they’re just cautious, their free time is limited, or maybe they’ve had some bad experiences in the past. On the other end of the spectrum, you’re going to have people who hate the digital conversation and would much rather meet up in person to get to know someone.

Which of these two types of people is right? The answer is that both of them are right. Neither approach is wrong. But, what is wrong is assuming that the person you are talking to has the same approach as you.

For example, if you’re someone that hates the digital conversation and would much rather meet in person but the match you’re talking to likes to take things slowly and get to know people first, you need to understand and accept that.

Yes, this means that you’re going to have to come out of your comfort zone a little and continue the conversation online longer than you normally would. But, if you really like the person, you’re going to have to do this.

If you’re the person who hates the online conversation, you’re always going to have to be the one that bends a little and waits a little longer. You can be expected to wait longer, but you can’t rationally expect someone who isn’t comfortable meeting that quickly to change their step. If you try and push this, you’re going to lose them for good and that opportunity will be gone.

Feel things out and you should have a pretty good idea of what you’re dealing with. You’ll see in the next few sections that if they are hesitant to meet initially, it might be because of this.

The Level of Conversation so Far

Second, you’ll want to look at the level of conversation so far. If you’ve sent two or three messages back and forth without a lot of substance, it’s probably too early to head out to meet someone unless you both are those kind of people. If you’ve been chatting for a couple of weeks and the conversation has been great and consistent, then it might be time to start looking for an opportunity to meet in person.

What Dating Site You are On

A lot of this is going to depend on the dating site that you are on. If you’re on a dating site that is more geared towards hookups (something like Tinder), then you should be moving to meet up sooner than later. It’s a very surface level dating site where it’s really set up to get people to meet up in person on a much quicker time table.

But, if you’re on a dating site that is more geared towards higher-quality and more serious relationships, then the time table usually slows down a little bit. When you are dealing with people that are taking the process a bit more seriously, they’re going to be more protective of their time and themselves.

The Bottom Line

Some of you still might not be sure when the right time to ask is. Here’s the bottom line advice. There is nothing wrong with asking someone at any point if they would like to meet up in person for a date.

But, you’re going to have more luck if you wait at least a week or two and after significant dialogue has been had. If they say no or that they’d like to chat more, respect that and wait longer. We’ll cover what to do if you get that response (or any other response) in the next few sections.

How to Transition to Meeting in Person for a Date

So, we’ve talked about when you should ask to move the dating process from the online realm to in person, but now we need to talk about how to do that. Here’s the good news. It’s really simple! People have a tendency to try to overcomplicate or overthink things when simplicity is the real answer.

The best way to transition to go on an actual date with someone from an online dating site is to ask. Seriously, it’s that simple. All you have to do is tell them you’re enjoying getting to know them and you think it’d be cool to meet up with them in person and see if you click.

Here’s a few sample ways that you could say this in a message. Feel free to use these word for word if you want to .

“You know, I’m really enjoying getting to know you. Would you be interested in meeting up sometime in person to see if we click?”

“I really enjoy talking with you. Are you this cool in person? Maybe we can find a time to find out?”

“You really are different and I like it. Would you have some time next week to get together and meet in person?”

It’s really that easy. Tell them you enjoy them and you want to see if things are the same in person. Now, once you ask the question and they say yes (we’ll cover if they say no in the net section), then you do have a few more things to do in order to make sure it actually happens.

You’ll need to suggest an activity and a few times/days that work for you. You can have this information ready beforehand (and we encourage you to) so that you aren’t fumbling and look lost when they say yes. Suggesting actual days is a good idea because it helps to move the process along.

Also, choose an activity that is non-threatening. We get it that some people want to do crazy lavished first dates, but a simple coffee date or grabbing a drink is plenty. You can do lunch or dinner if you want, but we like to opt for the easy-escape dates in case it’s not a good fit. And, if you’re going on a lot of first dates, there’s nothing wrong with saving a little money.

Here’s what this might look like after they say yes. Again, feel free to use these word for word if you need to.

“Great. Does Tuesday or Wednesday night next week work for you? Maybe we can grab some coffee or a drink?”

“Awesome! Are you free Thursday or Friday night this week? We could go grab a drink.”

Again, it’s that simple. Once they confirm for one of those nights and agree to the activity, go ahead and suggest a location. This part you could wait to come up with until this part of the conversation if you don’t know where they live. Ideally you’ll want to suggest a location that is somewhere close for both of you to get to which will require you to know at least what side of town they live on. You don’t need their actual address (and you shouldn’t ask for it). Just ask them what side of town they live on so you can pick a place close by. Once they tell you, hit Google and find a place if you don’t know one off the top of your head. Suggest it and get a confirmation.

Once they confirm, you should confirm everything so it’s clear.

“Great, I’m excited. I’ll meet you at Larry’s Tavern in the bar area at 8pm this Friday night.”

Obviously, fill in the right details for you unless you’re actually meeting at a Larry’s Tavern this Friday at 8pm which would be crazy.

What to Do if They are Hesitant

You are not always going to get a yes the first time you ask an online date to take things offline. That’s okay. This IS NOT a form of rejection. The fact that they are still talking to you and getting to know you should reinforce that. As we said earlier, some people just like to take things slower and get to know people before they commit to meeting them in person.

Now, there is a limit on this of course. If they keep putting it off and making excuses over and over again, there maybe something fishy. If this is happening to you, make sure you take a long look at things. If you’ve been regularly chatting with someone in your area for over a month and plans haven’t been made to meet yet, you should start to get a little hesitant unless they have a very good reason. Spoiler, there are very few good reasons. If it goes over the two month mark, it’s 100% time for them to meet up with you or for you both to go your separate ways.

But, if they are just hesitant and want to get to know you better (and it’s inside the time window we just laid out) then that’s totally okay. You have to be patient and respect their wishes.

Here’s the best way to handle things. Tell them something that puts the ball in their court.

“No worries! I totally understand. Let’s keep chatting and getting to know each other and when you’re ready to meet in person, you let me know and we’ll get something planned. Sound good?”

This takes all the pressure off of them, respects their wishes, lets them know you’re ready to meet but willing to be patient, and puts the ball in their court. Now, you can sit back and just wait for them to bring up meeting up. They’ll be fully aware that you want to, so you don’t have to worry about bringing up the issue again.

The only caveat here is that the time frames we laid out are still in effect. If it starts to get to that 2-month mark and they haven’t said anything about meeting up, you can bring it up again. This time we would say something like this.

“Hey! Have you given anymore thought to meeting up in person? I love talking to you online, but I’m looking for something that could potentially turn into more than just an online thing.”

Again, it’s not pushy, but it’s clear about what you are looking for and forces them to give you an answer. If they keep giving you something about wanting to wait longer, then it might be time to cut the cord and move on. Either they are catfishing you or more than likely they’re just not serious about finding anyone special and just like the attention online.

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.