We’ve all been there. You see someone you want to talk to—online or in person, and freeze. What should you say? How do you not sound awkward or robotic? Whether it’s a potential friend, colleague, client, or mentor, knowing how to start a conversation is a powerful skill that can open doors, build relationships, and ease social tension.
The good news? You’re not alone in feeling unsure. Even the most confident people sometimes struggle with the first few words. The better news? There are simple, proven conversation starters online and offline that actually work.
Let’s break it down.
Why Starting a Conversation Can Feel Difficult
Starting a conversation is universally tricky, not because we don’t want to connect, but because we’re afraid of rejection, judgment, or just running out of things to say.
In real life, you might worry about interrupting someone’s day. Online, you might feel awkward sending a message out of the blue. And when it’s work-related? The pressure only gets worse.
But here’s a truth worth remembering: Everyone appreciates a good conversation. The key is knowing how to begin it thoughtfully.
Conversation Starters That Work in Any Situation
Great openers are not clever tricks. They’re about showing interest, being present, and keeping it simple. Here are a few universal starters that can ease the tension:
- “Hey, I really liked what you said about [topic] earlier—mind if I ask more about it?”
- “This is kind of random, but I thought I’d say hi—how’s your day going?”
- “What brought you here today?”
- “I saw your profile and we seem to share a few interests—mind if I reach out?”
These may seem basic, but that’s the point. Authenticity beats performance every time. The best openers for messages or in-person chats are the ones that feel like you, not a script.
How to Start a Conversation Offline
When you’re face to face, non-verbal cues do a lot of the heavy lifting. Still, those first words matter.
1. Make Eye Contact and Smile
Before you say anything, make a connection with your body language. A simple smile and eye contact can show openness and warmth, making others more receptive.
2. Use Contextual Cues
Look around for conversation fuel. Are you at a conference? Ask what they thought of the last speaker. Waiting in line? Joke about the wait. Shared surroundings create natural conversation starters.
3. Ask Open-Ended Questions
Skip the yes/no questions and try something like:
- “What made you decide to attend this event?”
- “How did you get into your field?”
- “What’s something you’re currently working on that excites you?”
These kinds of questions invite stories, not just answers.
How to Start a Conversation Online
Thanks to technology, starting a conversation doesn’t have to mean walking across a room anymore. But even online, how you open matters.
1. Via Messaging Apps (e.g., InfoPhone)
Whether you’re using personal chat apps or platforms like InfoPhone, your goal is to break the ice without sounding spammy. These secure messaging for networking platforms are perfect for starting thoughtful, private conversations.
Start with:
- “Hey, I came across your profile, really liked your project on [topic]. Would love to learn more.”
- “Just wanted to say hi and connect, I’ve been following your work for a while!”
Avoid overly formal intros, write like a human, not a pitch deck.
2. Social Media & LinkedIn
Here, personalization is key. Refer to something specific, like a post, article, or shared connection.
- “Saw your post on [topic] and it really resonated. Do you mind if I ask you a question about it?”
- “We’re both in [industry] and I’ve been meaning to connect. How’s your experience been with [relevant detail]?”
3. Online Communities & Events
When joining a group or virtual event, it’s easy to feel like an outsider. A friendly intro in the chat, or replying to someone else’s message with curiosity, goes a long way:
- “Loved what you said about [topic]—totally agree!”
- “Thanks for sharing that link—mind if I message you to discuss more?”
The same conversation starters online principles apply: be relevant, be kind, and be curious.
Do’s and Don’ts of Starting Conversations
Do’s
- Be Authentic and Approachable: People can sense when you’re being real versus rehearsed.
- Keep the Tone Friendly: You don’t need to be overly formal or casual—just natural.
- Personalize Your Opener: Mention something specific to show you’re paying attention.
- Show Genuine Interest: Ask questions because you care about the answer, not just to keep the chat going.
- Ask, Don’t Assume: Avoid jumping to conclusions or making the conversation about yourself too soon.
Don’ts
- Don’t Lead with a Sales Pitch: Nothing shuts down a conversation faster than feeling like a target.
- Avoid Overused or Cliché Openers: “Hey” or “Wanna connect?” doesn’t give anyone a reason to respond.
- Don’t Force Conversation: If someone isn’t engaging, that’s okay. Move on with grace.
- Avoid Controversial or Personal Topics Too Soon: Keep it light and neutral until trust is built.
Tools That Can Help Start or Continue Conversations
We all need a little help sometimes. Here are some tools designed to take the pressure off and keep conversations flowing naturally.
InfoProfile – Digital Business Card
Use InfoProfile as your silent introduction. This personal digital card lets you share who you are, what you do, and how to reach you—all in one neat link. Great for following up after first contact, or even for initiating conversation with a simple: “Here’s a little about me—happy to connect!”
It’s one of the smartest conversation starters online when you don’t want to talk too much.
InfoPhone – Secure Messaging
Once you’ve made initial contact, InfoPhone helps you follow up securely and comfortably. It’s private, encrypted, and distraction-free—ideal for one-on-one chats that feel authentic, not performative.
This platform is especially helpful if you struggle with small talk and want space to think before you respond.
Scheduling Tools
Sometimes the best move is to take it offline. Use scheduling apps to set up virtual coffees, phone calls, or brief chats at a time that suits you both. It makes things easier and signals that you value the person’s time.
Message Templates
Not sure what to say? Start with templates designed to initiate real conversations. Many tools now offer AI-assisted openers, or you can keep your own bank of tried-and-true phrases. It’s not cheating, it’s planning.
In Conclusion
Here’s the truth: no one feels 100% confident starting every conversation. But with practice, the right mindset, and a few digital allies, it becomes easier. Whether you’re using InfoProfile to break the ice or InfoPhone to keep the dialogue going, small efforts can lead to big connections. Try just one new approach today—whether it’s sending a message, starting a chat, or replying to someone online.
You never know what one good conversation might lead to.
