How to Start a Conversation With Anyone, Anywhere, Anytime

Do you want to know how to walk up to a perfect stranger– any perfect stranger– and start a conversation?

No, unfortunately, this isn’t an infomercial for an all-in-one charm-inducing drug which may or may not have been medically tested yet.

However, the good news is there are a few basic principles which most relationship experts have found work wonders in virtually any situation and with anyone.

So, whether you’re looking for that special someone and want to know how to most effectively start up a conversation in the most unlikely of places, like the supermarket, or you’re a business professional looking to improve your social skills so you can build your network, these strategies will help you start up any conversation easier.

My idea of a good night has always been having a lovely meal and a proper conversation.

– Kirsty Gallacher

Here’s how to start a conversation with anyone:

1. Always start with a question

Always start with a question. Why? Because a question opens up the conversation for further dialogue and shows the person you’re interested in them.

The last thing you want to do is make a statement, which may or may not result in the kind of response from the other person that leads to a natural follow-up, immediately leading to an awkward silence and missed opportunity.

A question allows you to keep this from happening by controlling the conversation and sending it in a favorable direction.

2. What kind of question should I ask?

Photo Credit: Alex Holyoake on Unsplash

The first thing that likely comes to mind is “So, what question do I ask?!?”

First, make it an open-ended question. Open-ended question helps us do what we talked about in the previous point by opening up the conversation.

Next, stay away from touchy subjects like politics, religion, and even family. Especially politics and religion, which can turn a friendly introduction into a heated goodbye in the blink of an eye.

Family isn’t always a bad subject, however, you never know if they’ve recently lost someone recently or just don’t get along with parts of their family, so that can bring up some depressing or sour feelings. And, clearly, that’s not the direction you want the conversation to go.

Instead, ask questions like or pertaining to:

• Where they work: If they’re a co-worker, you can say something like “Hi, I keep seeing you around and I’ve been meaning to say hi. What department are you in / what’s your position / what do you do here?” Each of those questions can be interchanged, and followed up by another question asking them how they like working there.
• Where they live: If they’re a neighbor or you simply met them in a local store, you can ask them if they live around here and then how they like it, what they like most, what they like to do in the area, etc.
• What they’re wearing: Maybe it’s a brand you like, a piece of jewelry they’re wearing that you think looks cool, or a patch or pin they have on their bag or backpack. Ask them if they always wear the brand, how many pairs they have of X shoe, tell them how much you like their necklace and ask them where they got it, etc. This is one of the best options because there are countless things you can tease out from looking at what someone is wearing or has on them, around their workstation or cubicle, etc.

Some of these are better as openers and others follow-ups, but each of the above points has several of each type of question you can mix and match to jump-start a conversation.

3. Then, really listen

This is one of the most important steps but something that most people are rubbish at.

Listening is critical because it allows you to give a relevant response that not only shows the other person you were listening but tells them a little about yourself.

When you’re really listening, you often pick up on bits of information that naturally lead to follow up questions and comments that naturally move the conversation forward.

Seriously, if you haven’t taken the time to really learn how to listen then do yourself a favor and do that now.

4. Finally, make a (relevant) statement

A great conversation is a balance between questions and answers.

That might sound super basic, however, in actual practice most of us either talk the other person’s ear off or have been misinformed that repeated questions will allow us to control the conversation and lead the other person to think that we’re interested in them.

You want to start, and base, the conversation in open-ended questions. However, you also want to respond to their answer with your own statement instead of rolling into another question. That will make the other person feel like they’re being interrogated.

So, if you said you like their Toms and asked them how long they’ve worn them, after they answer you can comment on how you’ve worn Toms for years too (remember, you need to pick something relevant that allows you to have a response like that).

Keep in mind that once you’ve gotten to this point, you might need to ask another question and follow the sequence through again before things get rolling.

However, once things do get rolling that’s when a conversation becomes much more effortless and natural. In other words, you’ve succeeded.

5. And don’t hold back your enthusiasm

One last, very important point: don’t be afraid to get excited.

Your first inclination might be to suppress your energy and enthusiasm, hold your hands in your pockets when you want to gesture, and generally stay “cool”. However, we typically react more positively to shows of enthusiasm through hand gestures, facial expressions, and teasing our voice with different tones and volumes.

This makes a conversation more interesting and we all rather be around someone fun and energetic than someone dull and lifeless.