You had the courage to get up and go talk to someone new, and there you are saying “hi” and starting a conversation. Great!

You feel nervous, anxious, but you are doing it. A minute or two into the conversation, you stumble upon one of your worst fears: the other person doesn’t help you make conversation and you are stuck.

You know how this continues from there. You get even more anxious, you may ask question after question and bore yourself and the other person or even worse, you just stay there in awkward silence and eject from the conversation feeling defeated.

This happened to me multiple times. I know how painful it is.

How to solve this?

Here are a few ways to deal with it:

1. Ask a question and immediately answer it yourself

   Example: “Hey, do you like this song? I was, in fact, at this band’s concert last month. I went with some friends and it was, honestly, one of the most memorable experiences I’ve had.”

   Before I explain why this can work, can you guess why? (Tip: Try to imagine someone else is saying this to you. How would you react?)

   There are a few reasons this can work:

   • You are introducing a new subject and they might find it interesting.
   • You are conveying more of your personality.
   • You are leaving out some information which may intrigue them, leaving them wanting to know more.

2. Tell a story or joke, or anything that doesn’t require the other person to actively participate

   Let’s be honest, we all like listening to a good storyteller.

   If you possess the skill, either because you developed it naturally or because you practiced it with us in class, this is a great time to put it to use.

   The great thing about getting into this type of monologue is that it’s totally acceptable and highly entertaining. If you instead just talk and talk about anything else that doesn’t have the story format, people will get bored and won’t know if you are ever going to finish.

   The magic of using a story is that it has an end. You’ll eventually get there, and because of this, others will have fewer doubts when deciding to stay to listen to it.

   Important: Make sure you introduce your story in a compelling way. Create suspense and intrigue from the beginning. If you preface your story with a time constraint, that’s even better, as you’ll be signaling that they won’t need to be there for too long.

   If your storytelling skills are good, they’ll be hooked, and little by little you will see their demeanor changing.

3. Talk to the person next to them, bring them into the conversation

   I am not inventing all these techniques out of the blue. I’ve used them myself when I found myself in these situations.

   For this particular technique, I remember one time in particular, when I was trying to talk to a girl I liked. She was with one of her girlfriends. I saw other guys trying to talk to her and failing, and realized that the direct approach wasn’t going to be that good.

   I approached her, said hi, and she didn’t reciprocate. She was dancing. Her friend wasn’t. So instead of leaving, I turned to her friend and started talking to her.

   This way I was facing both of them, and from time to time I checked with the girl I liked, or asked her something related to what I was talking about with her friend.

   By the end of that night, she gave me her number and we went out the night after.

   Why did this work? In this particular case, I know because she told me. The reason she wasn’t giving much attention to the guys approaching her or me was that she was there for just one reason: she wanted to dance. She liked that I didn’t push too much on trying to talk to her and found it fun that I was able to entertain her friend and be social like that.

These suggestions work better if you haven’t already reached a point where the conversation died, since it’s harder to fix the conversation than to make it right from the beginning.

Final thoughts

Like with anything social skills related, there’s no magic solution and it will depend case by case. If you apply one of these techniques with someone you want to talk to, don’t do it more than once or twice. If they still don’t reciprocate, you’ve done all you could and can move on now.

Staying relaxed and not showing yourself affected by the situation is key.

Once others feel you really want their attention, they’ll reject it, because it will trigger the feeling that you want something from them. Don’t be pushy and instead try to enjoy yourself.