December 17

How to Start a Conversation with an Online Date



How to Strike Up a Conversation with an Online Date

You have made it from the app to the date. Congratulations, the hard part is over! Now comes the second challenge, how do you keep the conversation going?

It is normal to feel a little nervous on a first date with someone that you met online. There is some pressure from the build-up to the date and there is the small fear that you don’t have chemistry in person.

Even if sparks don’t fly from the very beginning, enjoying the conversation improves your chances of a second date. This is how you can keep them engaged throughout the date.


Stage 1: Starting the Conversation

The beginning often feels the most awkward for people. This is the stage where they are not yet sure how to behave around the other person.

After the usual, ‘hi, how are you? Did you get here okay?’ etc. the real conversation starts. So, what should be your opening lines?

Remember that you have already had successful conversations online. They are an excellent place to start your conversation.

You can score points by showing that you truly paid attention to those earlier online chats. Mention something that you learned about them from the online messaging.

Here are a few examples of how to start the conversation.


At a restaurant:

– Since you’ve been to (country X), what would you say is the most authentic food you can find on this menu?

– I know you love dessert. Should we go a little crazy and start with dessert? Or how about we order one of everything on the dessert menu?


On a coffee date:

– Okay, let’s put it all out on the table. How addicted to coffee are you and how long do you think you could go without it?

– You told me this is your go-to coffee order. Convince me why it is the best.


On an active date:

– How often do you think we have to do this to look like we are related to (their favorite superhero)?

– Imagine (2 athletes/celebrities they like). Who do you think would be better at this?


At a bar:

– You haven’t told me your favorite drink but can I guess? I’ll tell you why I think it’s your drink and if I’m wrong I have to drink it myself.

– What is the bar scene like in (where they are from)? If I ever went, which bar do I absolutely have to go to?


Stage 2: Keeping the Conversation Going

Now you have made it through the first part of the date. On some dates, this could be the part where you run out of things to say and the awkward silences begin.

A few seconds of silence is fine but if they are too frequent or too long, your date isn’t going so great. Another bad sign is if they seem to be trailing off with their thoughts.

So, how do you keep your date engaged in the conversation? The best tactic is to ask them questions about them – talking about yourself is the easiest thing to do.

What will keep the conversation going is more open-ended questions, things that they need to think about and explain. A question that you could answer with 3 words or less and doesn’t lead to any follow-up questions won’t add much to the conversation.

These are examples of open-ended questions you can throw in.


At a restaurant:

– If you think of home, what meal do you associate it with the most? Usually, meals are associated with memories so what is the memory that you connect that dish to?

– How good are you at reading people? Look at that couple over there, what do you think their life is like?


On a coffee date:

– Do you think someone’s coffee order says something about them? What coffee order would you assign each person here?

– If you could accidentally on purpose spill a drink on someone, who would it be?


On an active date:

– What sport do you wish you were really good at? Olympic level good.

– What is your favorite music to work out to? If you could only listen to 3 songs when working out for the rest of your life, which 3 songs would they be?


At a bar:

– What do you think is the best way a guy can approach a girl at a bar?

– Tell me about your favorite night at a bar and your worst night at a bar.


Stage 3: Ending the Date

The final stage of a date is critical. This is the point where you need to really convince them to go on another date with you.

If the conversation went well so far and they didn’t cut the date short, you should be fine. Keep this in mind so you don’t get too nervous.

Although you get into a little more detail on the first date, it is not the time for your complete life story, either. The end of the date is when you want to leave a few Easter eggs so that they are curious about what they would find out about you on the next date.

Like at the start of the date, it is good to show that you were really paying attention to the conversations. If you can refer back to something they said earlier on, you are showing that you are an attentive person.

These examples are a good lead to asking for a second date.


At a restaurant:

– This dish was really good but I’ve heard amazing things about this dish at (restaurant X). I think it is only fair that we try them both.

– Now that we’ve had (brunch/lunch/dinner). I’m really curious what you would order for (brunch/lunch/dinner). You told me about your favorite (brunch/lunch/dinner) place.


On a coffee date:

– I know that coffee dates are supposed to be short and sweet but say we had the time, where would you like to go after this?

– I would come to this coffeeshop every day if I knew I would run into you again. So, when can I run into you again?


On an active date:

– This was good exercise! Next time, can I show you what I look like without the sweat?

– Is there an activity you’ve never done before but always wanted to try? Let’s make it happen!


At a bar:

– If you were to have a terrible hangover tomorrow, would tonight still have been worth it? What’s your hangover cure?

– You have been drinking (their drink) all night. How about we go to a bar with more (their drink) variety next time?


These first online date conversations are meant as ideas that you can fall back on. These are conversation topics that almost anyone could talk about.

Keep this tab open your phone and take a quick sneak peek when your date won’t notice. It will bring your date right back on track.

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