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How To Approach Strangers And Start A Conversation

As part of my ambition to continually better myself, I am trying to expand my social circle by approaching people more people and being more open to other opinions, culture and ideas. I have found that being comfortable with my own company, I have an inherent fear that I may not actually enjoy talking to a stranger, even when I have found their appearance interesting. In my habit of seeking solutions to my problems, I have compiled the tips below, which I share with you today, in the hope that you might also make use of them if need be.


Tackle Your Anxiety: You might be surprised but the best way to tackle your approach anxiety is through “practising by approaching people”. Now, this may sound like it’s bringing us back to the topic but the idea here is to help you take steps that will make you more comfortable with people and not to become a social butterfly immediately. So we are going to adopt a step by step approach thereby easing the process and conquering bit by bits of your fear. Start by:

  • Writing down the worst things that could go wrong if you approach someone new and how you can negate them. Also, think about how strong your confidence becomes when you take action and what you stand to lose if you don’t
  • Start to say HI to 3 new people every day and increase it to 6 after a week and so on. At the end of your 6th week add giving genuine compliments to 5 of the people you say HI to.

Open Non Verbally:
Talking to a person without giving them a hint that you were going to approach them can create a strange feeling in them or even startle them. Instead of walking up and starting a surprise conversation with the side of someone’s head, ease into it non verbally(e.g waving a little). Make eye contact and give a smile to establish a connection before trying to start a conversation.

Look Approachable and Friendly:
If you look anxious or grim when you open up a conversation, you’re going to put the other person on edge immediately. Even if you feel like a mess inside, try to look relaxed and friendly to put other people at ease. This will result in better, longer conversations. To do this:

  • Make eye contact and don’t press your phone
  • Smile
  • Don’t cross your arms over your chest. People might interpret crossed arms to mean that you’re closed off or uninterested in the conversation.

Phase 2: Opening With A Small Interaction

Highlight A Similarity:  Whether it’s a shared interest, hobby, or sense of humour, pointing out something you have in common is a great way to approach someone you want to be friends with. It shows that you’re paying attention and are interested in the other person and can set the stage for future conversations and outings, and a friendship. But make sure that you do not try to force it by trying to be someone you are not.

Ask an open-ended question: If you ask questions that have yes or no answers, the conversation could stall quickly. Instead, ask questions that encourage the conversation to open up rather than close down. For example:

  • “What have you been up to today?” instead of “Are you having a good day?”
  • “I’ve seen you here a lot. What keeps you coming back? What’s so great about this place?” instead of “Do you come here often?”

Offer or Ask for Help: Everyone likes to feel like they’re an expert on something. Even if you know a lot about the subject you end up talking about, ask the person to explain things to you. For example,
if a news event comes up, say “Oh, I saw some headlines, but didn’t have time to read the article at work today. Can you tell me what that was about?” People enjoy conversations more when they feel like they have something to teach.
Also, letting someone know that you’re there if they need help, (e.g., solving a problem with a school or work assignment, or even with some heavy lifting) is a great away to approach them and subtly let them know that you’re interested in being friends. This can work out especially well if you’re able to work together toward a common goal.

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Use humour:
This approach isn’t for everyone, and it can be harder to pull off if it’s not something you’re used to. It’s not about knock-knock jokes and it’s definitely not about trying to show off your wit or charm. It actually has very little to do with impressing someone else and everything to do with trying to make both of you feel more at ease. Sharing a lighthearted comment or joke, your penchant (pun-chant?) for puns, or your tendency to be self-deprecating gives the other person a glimpse of your personality and can be a great way to connect. Just remember, it’s best to avoid putting someone else down, even in a joking way. And don’t be too hard on yourself if your humour doesn’t land.

PHASE 3: Taking Action

Attend Social Events:
The idea here is “putting yourself out there”, attend social events alone, keep these outings low-stakes. If you don’t talk to anyone for the first couple times, that’s fine! You still went out and were among strangers, which you never would have done before! Look for events around town where you’ll be able to start conversations with strangers:

  • Art shows
  • Book readings
  • Music concerts
  • Museum exhibitions
  • Outdoor festivals
  • Geek gatherings
  • Parades/rallies/protests

Don’t Overthink It:
If you obsess over all the ways things can go wrong before you start a conversation with a stranger, you’re setting yourself up to fail. The more you think about it, the more anxious you’ll get. When you see someone you want to talk to, break the ice immediately before you have a chance to talk yourself out of it. The adrenaline of the moment will carry you past your nerves.

Don’t Let Rejection Weigh You Down:
When you start putting yourself out there, you may well get the brush-off from someone you approach. But as a shy person, you know perfectly well that sometimes, people just don’t feel like talking. If someone rejects your approach, don’t take it personally!

  • Try to see failure as exciting — it’s a chance to learn and improve.
  • People don’t bite. The worst thing that can happen is that someone will say they’re busy or want to be left alone. That’s not the end of the world!
  • Nobody’s watching or thinking about you but you. Don’t worry about people laughing at you — they’re all busy thinking about themselves.

Be upfront:
If you’ve had only brief interactions with someone you want to get to know better, it’s absolutely okay to share that you’re looking to meet new people and that you’ve really enjoyed the conversations you’ve had so far. Being direct about your desire to make new friends doesn’t have to be a big scary thing. Casually let them know that you’d be happy to chat again or get together in a different context (e.g., “Hey! I really enjoyed our conversation! Any chance you’re open to grabbing a coffee sometime?” or “I actually just moved here and don’t really know anyone. I’d love to find time to hang out and maybe go for a walk together!”). People are often far more receptive to this than we expect. They might even be relieved that you made the first move!

Photo by Helena Lopes on

Thank You! for reading I hope this helps and remember don’t overthink it, you don’t have to master all the tips here, take action and you might be surprised at the results you get.

Quoted Sources:
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Life hack

2 replies on “How To Approach Strangers And Start A Conversation”

These were just the right guidelines I have been seeking for this issue. I’m glad I came across your blog article. I can’t thank you enough for writing such a helpful post.

I am so happy to connect with you. I have followed your blog, and I must say you are doing a fantastic job.

I also write about similar topics, so feel free to check out my blog as well. Someday, we could even collaborate on some interesting projects.

Kiran Kandel


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