It’s all very well talking about building good relationships and good dating tips, but if you like someone, how do you start talking to them? How do you go up to someone and start a conversation without it being totally awkward? There is no fool-proof plan, but there are things we can do to make it less daunting and something we can do. 

‘I wouldn’t know where to begin. If I like someone, I can’t just go up and talk to them. I don’t know what I’m doing’.

This is what a friend said to me recently. He’s single at the moment but one day he wants to start dating and eventually get married. But people he likes and notices, he avoids. He can’t talk to the people he wants to talk to.

Trying to start a conversation with someone we like can seem like the hardest thing

Ironic right? But probably something a lot of people can relate too.

Trying to start a conversation with someone we like can seem like the hardest thing in the world. I dreaded it when I was single.  I can’t offer you any guarantees, but I can try to make it seem less daunting, and offer us something to help us get over feeling like ‘I just can’t do this’.

What You Should Do

If you like someone you’ve know for a while, or just met for the first time, these bits of advice can help you start that chat. What you should remember is:

  • Eye contact
  • Smile
  • Make the opening line topical
  • Listen
  • Don’t lie

Eye contact 

Eye contact is really important. Obviously, don’t just look straight at them without ever blinking. That would be weird. But eye contact shows that you’re listening and you’re interested in them. This is important in any conversation, but especially this one.


It is simple science, if you smile, other people will feel more relaxed

This may seem like the last thing you want to do when you are nervous or worried. But it’s a very easy thing. Honest!

It’s simple science, if you smile, other people will feel more relaxed and feel warmer towards you. It’s really effective, and the one thing we can do easily, we just need to remember to do it!

So imagine, by this point you’re smiling and looking at them (but not staring). Then what, what do you say?

Make The Opening Line Topical

This is the thing that worries people the most. They think they need some slick or funny opening line, and try to come up with all sorts of things. From cheesy to the ridiculous.

The best and simplest thing you can do is try to make it topical

Yes first impressions are important, but I think the first line is better seen as a way to get the conversation started. Getting people to engage is more important than saying one ‘amazing’ sentence than having nothing to say afterward.

The best and simplest thing you can do is try to make it topical and avoid asking questions that can be answered with a simple yes or no.

For example, If you’re at a party, you don’t need to say ‘is heaven missing an angel?’. (Please don’t say that. Please!) Don’t say ‘Do you know Tim?’ They can simply say yes or no.

Rather, say ‘So how do you know Tim?’, or ‘How did you hear about this party?’. Topical, relevant, and gets the conversation going.

Take the pressure off yourself, it doesn’t need to be the best sentence ever spoken.


‘Ahh, but I’m panicking, what do I say next?!’ Sound familiar?

You may be able to think of two or three topical questions, but then what? Honestly, you need to just listen and try to let the conversation flow. Often people have a list of questions to ask in their head, and it becomes like an interview.

Don’t have a list of 10 questions your head

You need to listen to what the other person says. If they say they know Tim from work, there is no point saying ‘So what do you like to do in your spare time?’. It would be better to ask ‘So what do you do at the company? Do you enjoy it?’.

Just listen, don’t have a list of 10 questions in your head, listen and go with the flow.

Don’t Lie 

Please don’t lie. When we want to impress it can be very tempting to say something to get their attention or approval. But dating is about letting them see the real you, and vice versa, and deciding together if you want to commit to each other. (Read Dating Is A Marathon, Not A Sprint).

Lies will stop us building the relationships we want. Don’t get carried away in the moment.

Imagine If…

Conversations happen naturally all the time. Maybe because of the situation or your personality, these rules won’t be as helpful, but a lot of face to face chats with people we like can be made less awkward and feel achievable with this advice. Even if it’s still a bit nerve-wracking, we can make it less daunting. (Read about why we should be active in dating here)

Imagine if we remembered to do these things when we spoke to someone we liked. Eye contact, Smile, Make the opening line topical, Listen, and Don’t lie. We can then focus on trying to start something, rather than telling ourselves no to bother.

Also, when we see our friends getting worried, let’s resist the temptation to tease or say it’s easy. They’re nervous and probably need some practical steps and reassurance more than anything.

What helps (or helped) you when you speak to people you like? Comments welcomed below. 

Originally posted 27/3/2017