How to Start a Conversation with Your Date

start conversation with your date

December 11, 2020

Starting a conversation is not easy, especially if it’s with a total stranger or someone you are just getting to know. It might just be the hardest part in socializing but if you think about it, all the people you know now were once strangers to you. Every conversation brings a chance to learn something new, and who knows, the next person you speak to might just be your future partner. Initiating a conversation might not be the most comfortable thing to do, but here are some tips on how to start a conversation. 

How to start a conversation

While some people may be born with the gift of the gab, others (like us) may feel our mouths go dry when we are about to strike up a conversation with someone we do not know. Whether you are at a party, a work networking event or on a virtual date, here are some ways to skip the awkwardness. Everyone can develop good conversation skills with a little bit of practice. 

1. Don’t wait for the ‘Perfect Time’ or ‘Perfect Line’

There really is no perfect time or perfect line to start a conversation. Ever felt that the longer you waited to say something, the harder it seems to be?

While there are times that seem better than others, waiting for the perfect time to start or join a conversation will only increase the pressure. Just say hello. Know that the worst thing the other person can do is reject you. Most likely they will be happy that you took the first step in introducing yourself. 

2. ‘How are you?’ vs ‘Tell me about yourself’

Many times, we ask the question ‘How are you?’ after initial introductions. However, this question gives the other person a chance to decide whether to continue the conversation or end it. 

You will have to come up with the next thing to say if the person gives one word answers such as ‘Good’ or ‘Fine’. If someone starts a conversation with ‘How are you?’ try giving them something to work with. Keep it short but tell them something about your week. 

Photo by Austin Distel on Unsplash

An alternative would be to use the phrase ‘Tell me about yourself’. This open-ended question allows the other person to choose what they want to say and to steer the conversation on. They can decide what they want to talk about as well how much they want to reveal about themselves. It’s also a perfect question for virtual dates as most likely the other person wants to get to know you as well. 

3. Look for similarities

Common interests bring people together. Conversations around a shared hobby or experience help people to feel connected. Taking the effort to find similarities will help make conversation that is much more engaging than the usual small talk. 

If you are at a social event, use common information about the event to strike up a conversation. For example, if you are at a networking event for work, chances are other people attending the event are also from the same industry. You can ask them something about work or how they got to the event. 

4. Pay a compliment

You can complement the other person to start a conversation. For example, ‘Hi, I like your dress! You look really good in it. Where did you get it?’ Paying a compliment not only gives you a chance to strike up a conversation but also gives you the opportunity to say something positive about the other person. 

For virtual dates, you could do a quick scan of their background and compliment something that catches your eye. Give it a try and you’ll see how easy it is. After all, who doesn’t like to receive compliments? 

5. ‘What’s the latest in your life?’ 

If you are already an acquaintance, then you can use simple openings such as ‘What’s the latest happenings in your life? or ‘Catch me up on what’s happening with you since the last time we met’. These open ended-questions allow the other person to choose what he or she wants to talk about. It also removes the chances of asking the wrong question.

6. Ask for a favour

When someone helps you in any way, their subconscious mind tells them that you are not really a stranger. After all, they have already done something for you. The task doesn’t have to be a big one. 

For example, if you’re on your first real life date, you can ask the person for the time, or to pass a bag or help you open the door. If you’re on a virtual date, you can ask the person to ‘help’ decide which lighting is the best for the date, while you adjust your lamp. 

Try it and you might just be surprised how easy it is to break the ice by asking for some help.  

7. Body language 

You look more approachable when you have an open body language. Others are more likely to steer clear of you if you have your arms crossed and your eyes are looking down. 

Photo by Brooke Cagle on Unsplash

Try having a smile on your face when looking for someone to start a conversation with, even if you feel overwhelmed in a room full of strangers. Studies have found that people who smile are deemed to be more attractive. Looking approachable and having eye contact can make a huge difference. 


Starting a conversation with someone you do not know may not be easy, but with some practice, everyone can do it. Remember to be polite, keep it light and to be honest. The worst thing you can do is to puzzle over how to start the conversation. Relax, be yourself and allow the conversation to flow with some of these other date questions that you can use. You might just be surprised when the stranger you strike up a conversation with becomes a good friend. If you need some fun ideas for your virtual date, check out our Fun Virtual Dating Ideas and Tips.

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