One theme I’ve seen consistently in therapy sessions is this:
How do I talk to new people?
How do you start a conversation, come across as interesting, and actually build a friendship from that first interaction?
Almost every person I talk to believes they’re the only one struggling with this. The reality? It’s becoming increasingly common.
The way we engage with one another has shifted—much of our communication now happens digitally. And while that’s made connection more accessible in some ways, it’s also quietly eroded something foundational: our ability to make small talk.
I’ll be honest—I don’t love small talk either. But it serves an important purpose. It’s the doorway to deeper, more meaningful conversation.
Recently, I asked a client to simply observe moments where small talk might happen and notice what anxieties came up. They came back the following session with an unexpected realization: there just weren’t that many opportunities. Even something as simple as chatting with a cashier at the grocery store has largely disappeared with self-checkout.
So if you feel out of practice, it makes sense.
If you never developed confidence in starting conversations—or if you used to feel comfortable but now feel a bit rusty—you’re not alone. This isn’t as obvious or automatic of a skill as people assume. And for most of us, the hardest part is the very beginning.
So… where do we start?
How to Develop Conversation Skills (Without Feeling Awkward)
1. Lower the Pressure
Most people walk into conversations thinking:
- I need to be interesting
- I need to say the right thing
That pressure is what actually shuts conversation down.
Instead, try this shift:
? Your job isn’t to impress—it’s to be curious.
Curiosity naturally creates connection.
2. Use Simple, Repeatable Openers
You don’t need something clever. You need something reliable.
Try:
- “How’s your day been so far?”
- “Have you been busy today?”
- “What’s been keeping you busy lately?”
These work almost anywhere—and they invite more than a one-word answer.
3. Learn the “Follow-Up” Skill
What keeps a conversation going isn’t the first question—it’s what comes next.
If someone says:
“I’ve just been working a lot.”
Instead of switching topics, try:
- “What kind of work do you do?”
- “Do you enjoy it?”
- “What’s been the most challenging part lately?”
? This is where connection actually builds.
4. Use the 70/30 Rule
Aim to:
- Listen 70%
- Talk 30%
People tend to feel most connected to those who genuinely listen.
And ironically, asking good questions makes you seem more interesting than saying impressive things.
5. Have 3 “Go-To” Topics Ready
When your mind goes blank, fall back on:
- Work or school
- Hobbies/free time
- Upcoming plans
This keeps you from freezing in the moment.
6. Normalize the Awkward Moment
Every conversation has small pauses. That’s not failure—that’s human.
What matters is staying grounded instead of rushing to escape it.
A simple:
- “I feel like I’m out of practice with talking to people lately”
…can actually build connection, not hurt it.
How to Get Better at Small Talk (Yes, Even If You Hate It)
Small talk isn’t the goal—it’s the bridge.
Think of it as:
? The warm-up before the real conversation
Try This Simple Formula:
- Start light
- Ask one follow-up
- Share something small
Example:
“Have you been busy this week?”
? “Yeah, work’s been a lot.”
? “Same here—it’s been nonstop. What kind of work do you do?”
That’s it. That’s small talk turning into a connection.
Where to Actually Practice (Because This Matters)
Your client’s observation was spot on—opportunities are fewer than they used to be.
So now, practice has to be a bit more intentional:
- Coffee shops (instead of mobile ordering)
- Fitness classes
- Dog parks
- Waiting rooms
- Community events
Even brief interactions help rebuild the skill.
When It’s Not Just “Out of Practice”
For some people, this isn’t just about skill—it’s about anxiety, past experiences, or internal self-doubt that shows up in social situations.
That’s where therapy can help.
At Madewell Counseling, we often work with clients to:
- Build confidence in social settings
- Reduce anxiety around conversation
- Understand internal patterns that make connections feel harder
- Practice real-life communication skills in a supportive space
? Learn more: https://madewellcounseling.com
? Anxiety support: https://madewellcounseling.com/anxiety-therapy
Resources to Build Conversation Skills
Books
- How to Win Friends and Influence People – Dale Carnegie
- The Fine Art of Small Talk – Debra Fine
- How to Talk to Anyone – Leil Lowndes
- Quiet – Susan Cain
Online Resources
- SkillsYouNeed — practical conversation frameworks
- MindTools — communication and confidence tools
- Psychology Today — articles on social anxiety and connection
Final Thought
If starting conversations feels hard, it’s not a personal failure—it’s a reflection of how much the world around us has changed.
The good news?
This is a skill you can rebuild.
And like most things, it doesn’t start with a perfect conversation—
it starts with a simple one.