How to start a great conversation with anyone [in person or text]

Overcoming the fear of starting a conversation

And speaking of conversation (that was bad), were you ever scared of initiating one?

Even if you’re the most extroverted of the extroverts, I’m sure you can remember a situation where you felt ill at ease. Don’t worry, it’s absolutely normal! And if this sounds way too familiar to you, you can totally work on it.

Common fears and anxieties associated with initiating conversations

Sweaty palms, heart racing, the irrepressible wish to disappear underground… We’ve all been there.

The apprehension of being judged, the fear of rejection, or the uncertainty of not knowing what to say can often act as debilitating barriers to initiating a conversation.

Shall I even get started on social anxiety? And it gets even more challenging when you’re not speaking in your native language.

These fears, though universal and as any fears, are not insurmountable.

Starting a conversation: a skill to work on

Indeed, knowing how to start a conversation is nothing more than a skill — one that can be cultivated and refined over time.

Much like learning to ride a bicycle, learning a new language or mastering a musical instrument, the art of conversation can be developed through practice, patience, and a willingness to step beyond the comfort zone.

By acknowledging that discomfort is a natural part of the learning curve, we can liberate ourselves from the constraints of self-doubt.

Also, try to ask yourself this: “What if I say the wrong thing or make a faux pas?” The objective answer is probably: “It’s not the end of the world.” You can probably even laugh about it with the other person.

But of course, fears are irrational. So, keep reading to learn actionable tips and techniques aimed at overcoming the awkwardness. You can do it!

Understanding the context

Understanding the context before initiating a conversation is almost like unlocking a door before stepping through. It determines the tone, direction, and success of the exchange.

Formal or casual?

Whether it's a casual chat among friends or a formal meeting, recognizing the context is fundamental.

In social environments, conversations often revolve around shared interests, experiences, and personal connections. Here, the atmosphere is informal, encouraging open dialogue, fun and bonding.

Conversely, professional settings demand a more structured approach, emphasizing clarity, conciseness, and professionalism.

That being said, it all depends on the person(s) you have in front of you. If you already know them, you can adapt to their personal mannerisms, and you’re probably aware of the boundaries.

For example, you might have a colleague who loves jokes, and another who prefers to focus on work only. Basically, read the room!

The role of non-verbal cues

Non-verbal cues reveal emotions, intentions, and attitudes. Body language, facial expressions, and tone of voice serve as essential elements in understanding the underlying context of a conversation.

They also provide clues about the mood, receptiveness, and comfort levels of the participants.

Awareness of non-verbal cues complements verbal communication, so it’s worth spending time learning about them and observing them.

Body language

Body language is a key part of any conversation, across all cultures. We actually dedicated an article to body language:

• Body language around the world

The importance of positive body language to start conversations

Positive body language can significantly impact the success of starting conversations.

Indeed, our body language communicates volumes before words are even spoken. It shapes initial impressions, establishes rapport, and conveys confidence, trustworthiness, and approachability.

First impressions are often rooted in body language, especially if the interaction is between people of different native languages. It can put the other person at ease, favoring smooth communication.

Moreover, body language can help regulate the flow of the conversation. Using gestures or appropriate facial expressions to emphasize points can enhance communication and convey enthusiasm or empathy, making the interaction more dynamic and engaging.

Body language tips

Maintaining open and welcoming gestures, such as maintaining eye contact, having a relaxed posture, and offering genuine smiles, can create an inviting atmosphere conducive to conversation.

Confidence is another crucial aspect conveyed through body language. Standing or sitting upright, with your shoulders back, portrays self-assurance and assertiveness. Confident body language not only reflects your own mindset but also inspires confidence in others about the conversation and your intentions.

Active listening through body language is equally essential. Nodding in agreement, mirroring subtle movements, and showing genuine interest through attentive gestures demonstrate respect and engagement. This reinforces the sense of being heard and understood, fostering a more meaningful and productive conversation.

What are good ways to start a conversation?

Observation

The art of observing

Cultivating the art of observation enables individuals to perceive their surroundings, seeking cues that serve as potential bridges to connect with others.

By paying attention to subtle details, such as someone's clothing or accessories, you can engage in conversation naturally.

The environment as your ally

The environment can also provide cues and conversation starters. Whether it's a bustling café, an art gallery or a beautiful landscape, each setting presents unique opportunities for conversation.

And of course, we can’t forget the good old classic: the weather!

Examples:

• Wow, it’s so busy today. Do you come here often?
• I’ve never seen the grass so dull in this park, do you think this drought will ever end?
• Are you cold? We could go inside.
• I see on your tote bag that you’ve been to Lapland?
• Look at this house, wouldn’t you like to live here?

Open-ended questions

The power of open-ended questions lies in their ability to invite expansive and detailed responses, fostering deeper conversations and meaningful exchanges.

Unlike closed-ended questions that elicit simple "yes" or "no" answers, open-ended questions encourage individuals to express thoughts, feelings, and experiences.

Basically, you’re “forcing” — ok, let’s say “kindly inviting” — the other person to keep talking!

After all, there is nothing worse than a dialogue like:

• It’s nice here, right?
• Yes.
• :Uncomfortable silence:

Examples:

• I haven’t seen you in ages! How’s life?
• It’s so nice to finally meet you! How was your trip?
• I was thinking about going to this new restaurant. What’s your favorite food?
• Welcome back! How was your Spanish course in Seville?
• Congrats on your engagement! Tell me everything about your fiancé.

Compliments

The power of genuine compliments

I don’t believe anyone likes fake or exaggerated compliments. So, obviously, stay sincere. The intention behind a compliment is probably as powerful as the compliment itself!

Genuine, heartfelt compliments can really go a long way. When delivered sincerely and thoughtfully, compliments have the potential to uplift spirits and pave the way for friendly conversations. They can even make a person’s day!

How to give compliments respectfully

Be authentic

As stated, genuine compliments stem from sincerity. Don’t overdo it.

Be mindful of boundaries

Ensure that your compliment is respectful and appropriate (religion, culture, gender, etc.). Avoid remarks about personal appearance — unless you know the person well — as these can sometimes make people uncomfortable. Instead, focus on achievements, skills, or character traits.

Use positive language

Frame your compliments in positive language to convey admiration and appreciation. Phrases like "I appreciate how well you handled that situation" or "Your dedication to your craft is inspiring" convey positivity without crossing boundaries.

Consider the timing and context

Ensure it feels natural and relevant to the situation.

Examples:

• I was very impressed by your presentation at the conference. What’s your secret?
• I love your new purse! Where did you get it?
• You were very nice to the waiter, I’m sure he appreciated.
• I love what you did with your garden. What are these flowers called?
• Great pick; I love Italian food! How did you hear about this place?

Shared interests

Shared interests, the magic trick to start a conversation

Do you know anything as powerful as a common interest to get a conversation going? That’s probably the strongest bond you can form from the start.

It’s wonderful if you do share interests, but were you ever in a situation when you had absolutely nothing in common with someone? I have, and here are a few tricks to find common ground.

How to discover common hobbies or passions

• Observation and listening: As mentioned above, pay attention to cues in the environment or conversations. Notice clothing, accessories, or activities that might hint at shared interests. Listen actively to what others are saying to identify topics that resonate with both of you.
• Ask open-ended questions: Inquire about topics that are likely to uncover shared interests.
• Online profiles and social media: If you have the chance, explore online profiles or social media platforms to gain insights into people's interests. Mutual connections, posts, or groups they follow might provide valuable clues about shared hobbies or passions.
• Share your own interests: Sometimes, expressing your own interests can prompt others to share theirs, especially with introverts.
• Observe reactions to topics: Initiate conversations on diverse topics and observe the other person's reactions.

Examples:

• What do you enjoy doing in your free time?
• I see you have a picture of a Labrador as a screen saver, is that yours? I have one too!
• You seem to be drinking your coffee black, with no sugar. That’s exactly how I drink mine!
• Are you going to the gym? I try to go 3 times a week, but it’s hard to keep up, right?
• You came by bike, that’s awesome! I ditched my car 2 years ago and never looked back.

How to start a conversation over text

The age of texting

Nowadays, true, spoken conversations are rare. In fact, most of our interactions happen via a screen.

Text communication has become an integral part of our modern social fabric. And it went so fast that nobody really wrote “guidelines” for it.

We all have this friend or relative who writes an entire message, with greeting and signature, like an old telegram. And the other, who checks if you’re there — Hi, what’s up? — before continuing.

From staying in touch with our friends to conducting business, the subtleties of starting a conversation over text hold a unique place in our digital landscape.

So, how to start a conversation over text?

The subtleties of initiating text conversations

Obviously, body language is not a part of texting, which makes it very tricky.

Text conversations rely heavily on words, punctuation, and context. They also involve a lot — too many — abbreviations, so try to go easy on them. Oh, and be mindful of autocorrect!

Another crucial aspect is pacing and timing. Respect for the other person's schedule and responsiveness is key. In the era of “Right here, right now”, it’s important to avoid bombarding with messages or expecting immediate replies.

Additionally, being mindful of language and tone is crucial. Text lacks the inflection and emotion conveyed through voice or facial expressions, making clarity and context essential. Thoughtfully use emojis or punctuation to convey emotions or intentions accurately, and avoid any misunderstanding from the start.

Moreover, the art of initiating text conversations involves reciprocity and active listening. Encourage dialogue by asking open-ended questions, and avoid dominating the conversation.

Finally, here is a thing I keep reminding myself to help communicate clearly, especially by text or email: “People are not in your head!”.

Examples of engaging opening texts

• Hey! I just stumbled upon this coffee shop with the most amazing pastries. Would you like to go sometime?
• Hi there! It's been a while, but I thought of you today. How have you been?
• Hey! I just finished that book we were discussing earlier. The ending was crazy! What are your thoughts on it?
• Hi! I was thinking about our conversation about a trip to Italy. And I’m all in. Let’s plan it, what do you think?
• Hi, I just wanted to check on you after today’s meeting. I think the boss was a little hard on you. How are you feeling?
• Hey! I saw your pics on Facebook! Can’t believe you got married! Tell me all about it! 😃
• Hi there! I heard you'll be attending the conference next week. Looking forward to it! Any particular sessions or speakers you're excited about?
• Hello! Just wanted to check in. Are you feeling any better?
• Hey, I know you’re going through a difficult time and probably don’t want to talk about it, but I’m here if you need anything.
• Hey! Just saw a meme that reminded me of our inside jokes. Just wanted to brighten your day 🙂

How to start a conversation with a stranger

This is probably the most difficult conversation to start. Sometimes, it flows naturally, but very often, you need to “force” things a bit to get the conversation going.

Confidence and approachability are fundamental attributes when initiating conversations with strangers.

Approaching someone with confidence immediately establishes a sense of credibility and reliability. It communicates that you're comfortable in your skin and genuinely interested in engaging in a conversation.

When you appear approachable, open, and friendly, it encourages people to reciprocate and dissipates any awkwardness, making the interaction smoother and more enjoyable for both parties.

Tips to start a conversation with a stranger

• Maintain positive body language, as discussed above.
• Be authentic.
• Start with a friendly and appropriate greeting.
• Show interest and listen actively.
• Respect boundaries and the other person’s comfort zone.

Icebreaker examples suitable for strangers

• The weather today is quite unpredictable, isn't it? I'm Josy, by the way. Do you enjoy this kind of weather?
• I couldn't help but notice your bag with a rabbit on it. I absolutely adore rabbits! I'm Sebastien. What’s your name?
• This cake looks delicious, doesn’t it? Have you been here before? Any recommendations?
• The artwork here is fascinating! Do you have a favorite piece?
• Welcome to our headquarters! I’m Sixtine, so nice to meet you. Can I help you with anything?
• Oh, what a cute dog! What’s his name?
• Would you like me to take a picture of you next to this monument? Where are you from?
• Hey, cool concert, right? Are you a fan of this band?
• I really enjoyed this conference. I’m Romy from Bunnyville Tech, by the way, nice to meet you. What company do you work for?
• I've seen you here often at the gym. I'm Augustin, and I enjoy working out too. Any favorite workout routines?

How to start a deep conversation

Setting the scene plays a crucial role in laying the groundwork for a meaningful and profound exchange.

Here's how to start a deep conversation:

• Create or choose a comfortable environment.
• Establish trust and rapport.
• Set a respectful and non-judgmental atmosphere.
• Use body language, as seen above.
• Transition gradually from a light topic to a deeper one.
• Be vulnerable and genuine.

7 tips to start and maintain a good conversation with anyone

Here are 7 ways to make a conversation with anyone, in almost any context. You probably have your own tips too!

1. Approach with open and positive body language.
2. Start with a friendly greeting.
3. Find common ground.
4. Ask open-ended questions.
5. Give your full attention to the other person.
6. Respect boundaries and cues.
7. Read the room.

Common pitfalls to avoid

And speaking of reading the room, a lot of people forget this when starting a conversation. Does the other person really want to talk? Are they in a hurry? Are they having a bad day and simply don’t want to talk to anyone? Pay attention to their body language and facial expressions.

Many of us also have a tendency to over-talk, especially when trying to fill an uncomfortable silence. But conversation is also about listening.

Also, while it’s great and encouraged to show interest, too many personal questions might make a person feel uncomfortable and come off as intrusive — in some cultures more than others. Respect the other person's comfort zone and privacy.

Finally, a lack of eye contact or closed-off body language can convey disinterest or discomfort. Maintain friendly eye contact and open body language to show engagement and approachability.

To avoid these common mistakes, the keywords are “empathy”, “adaptability” and “authenticity”.

And as the conversation started, it must also come to an end.

If you’re always nervous when initiating a discussion, remember: starting a conversation is like opening a Kinder egg; you never know what delightful connections or fun anecdotes might pop out!

So, be yourself, sprinkle in some humor, ask intriguing questions, and let the magic of conversation unfold. Who knows? You might just spark a chat that leads to unexpected adventures or a good laugh — either way, it's a win-win!