Fun Conversation Starters You Can Use Instead Of ‘Hey how are you?’


If you’ve downloaded my Ultimate Guide to Texting Men, don’t forget to email me to get your free copy of the second edition where I’ve added a few things to help you get through those tricky texts you get from men. You can email me at iona (@)

There are moments in online dating or texting where your conversations may just hit a lull. Instead of ‘Hey’ or ‘How are you?’, here are some fun alternatives. Not all of them will work for you but it may give you a few ideas on how you can make texting fun. Here are a few of my favourites:

Conversation starters

1.What was the best thing that happened to you today?

In asking someone about the best part of their day, they automatically associate good thoughts to you. It also helps to create more of an emotional connection and has more depth than ‘what did you do today?’

2. I learned how to [insert thing you learned here]. What about you?

Telling someone what you learned today shows your outlook on life, even if it’s as simple as how to make tea like an Englishman it shows you appreciated the little things in life.

3. I saw a [insert thing you saw here] and thought of you.

People love talking about themselves. This statement calls for an open ended response and gets the conversation going.

4. If you were to date a Disney princess, which one would you choose and why?

This was one of the questions I asked Cristian before we went on our first day. I was feeling playful that day and had a genuine curiosity to learn what men thought about Disney princesses. Cristian called me right away to explain why he would choose Pocahontas and Ariel. It was one of the best conversations I remember from our early days of dating.

5. Sweet or savoury and why?

How people explain their answers says a lot about them. There are so many directions you can take with this. Keep it PG or you can get a little flirty with it.

6. Guess the lyrics

One of the things that create connection between a man and women is play. We create a connection and bond with each other based on how they make us feel. Imagine what you’d think of a person who constantly makes you laugh. Guess the lyrics is one of those games you can play all day. Start the conversation with a lyric and have the other person guess it. Take turns.

7. Riddles

Just like ‘the guess the lyrics’ text, using riddles in texting brings out a playful side of you. It also keeps the other person guessing – a good way to bring in some teasing.

In witnessing so many text conversations, one thing I’ve noticed is that men and women don’t flirt enough. I’ve seen so many conversations that start and go on with no flirting – just friendly conversations.

Want more tips to texting? You might like this Ultimate Guide to Texting.


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