How to keep a conversation going over text with your crush


Pre-pandemic I am the first person to end the texting on a dating app and just ask the person on the date. But the pandemic has changed the dating game and it involves a lot of pregaming to the dating (aka texting). It has made it important to learn techniques on how to keep a conversation going over text.

Texting can get boring very fast for most people. But there are ways to keep it exciting. Away from the usual how was your day and how are you that people don’t want to answer every day.

How to keep a conversation going over text:


conversation on text

The Meme Game texting

Switch to send each other memes. It is an excuse to get his/her Instagram as well. You can share inside jokes about a show you both watched, some random fact he/she told you, and work jokes. There are memes for everything. It is the new form of communication and can start a whole new conversation as well. You can send texts flirting as well.

You can send Instagram Reels and Tiktoks as well. GIFs can be super cute as well if they are related to your convo. There is a GIF somehow for everything!

Cheesy pick-up lines 

These will make the other person LOL. You can talk about how bad they are. If they have ever worked. What your favourite pick-up line is. There can be a whole conversation around this.

“Did you hear…couples that gym together always workout…;)” – anonymous

“Even during the corona pandemic, the most contagious thing is your smile” – anonymous

“Can’t spell quarantine without u r a q t” – anonymous 

Random pictures

Doing something exciting and fun send the person you are talking to a picture. You can discuss what you are doing and it can add to a wider conversation. This can even be food pictures! This can be your way of hinting they should come over for food or take you out for dinner.

Ask questions over text

How to keep a conversation going over text

Statements like lol, okay, and goodnight end conversations. To keep the conversation flowing ask questions. They can be as random as do you eat pineapple on a pizza to if you were an animal what animal would you want to be. These questions help you understand the person but in a quirky way.

Keep the questions open-ended and something someone can reply long messages to. Not just how are you but maybe what does a day in your life look like.

Don’t just make it question after question though this isn’t an interview. Keep it light by adding your own side comments. Extra points if you make them flirty.

Having a conversation with asking this or that can keep the conversation going. For example would you want to go bungee jumping or skydiving? coffee or tea? passenger seat or driver’s seat?

  • What is your favourite drink and why?
  • What do you like to do for fun?
  • If you were going on a vacation where would you go
  • would you rather live on the beach or mountains
  • what is your favourite season
  • what is your pet peeve
  • Is there a worst date you have been on what was it?
  • Do you have a favourite food. What is it?
  • If you could live on one food for life what would you live on

For more questions check out first date conversation questions blog.

What makes you think of them?

Doing something super random and have the thought what would your crush do in the moment? Or think they would really like something. Message them and let them know. People love being thought of and its a great conversation to have! It can be anything from having something super spicy and your crush loves super spicy things so it made you think of them. Basically anything!

Talk about food

If someone talks to me about food I can just go on and on. You can talk about your favourite restaurant or what you like to cook. Send each other pictures of meals. Share recipes and make plans to cook together. You can find out through this whether he likes to add spice to his food or is more safe with what he eats. If you are from different cultures you can share the best dishes from your own culture.

Send pictures of food it is a good way on how to keep a conversation going on text.

Voice notes

To spice it up a little and move away from texting send short voice notes on WhatsApp. This can be your way out if you don’t want to talk on the phone but don’t mind sending short voice notes. This is a great way on how to keep a conversation going on text with a crush.

Wrap up

At some point though texting does become boring if you reach that point just go for a phone call or a date. Maybe the other person is too shy to ask. What’s the worst that could happen? If they are talking to you they most likely want to meet as well. Not sure where to go on the date? We have the perfect first date ideas.

Don’t use texting just for fun and games if you aren’t looking for a hook up ask the other person what they are looking for so you can filter out by watching out for online dating reflags.


A place to find information on all things wellness, dating, food and movies related. Basically our version of Netflix and Chill. If you are looking for advice and want the unfiltered truth well you have come to the right place. Read our insightful blogs and you will leave inspired. Welcome to Pigeon Talk!

Leave a comment

Your email address will not be published. Required fields are marked *

18 − 8 =