Making Friends / How to Start a Conversation / Lesson 14

LESSON 14 · HOW TO START A CONVERSATION

Questions to Avoid on a First Chat

Thirty-two easy tips on which questions to avoid on a first chat, so new people feel comfortable and curious about you.

Some questions need trust first. Start light and earn the deeper ones.

30 tipsEasy things to say7-day plan

Start with tip 1

Jump to the 7-day plan

30 tips that really help

These ideas come from The Fine Art of Small Talk (Debra Fine), How to Talk to Anyone (Leil Lowndes), We Need to Talk (Celeste Headlee), and everyday practice. Pick one tip and try it today.

TIP 1

Why some questions land badly

Early in a friendship, trust is low, so deeply personal questions feel like pressure. Light questions let people relax and share at their own pace.

TRY THIS
Start light.

TIP 2

Avoid asking about age or weight

These questions feel judgemental to many people, and they rarely help a chat. Ask about interests and experiences instead.

TRY THIS
Skip them.

TIP 3

Avoid asking about money

Questions about pay, rent or prices can embarrass people and make them feel measured. Talk about what they enjoy, not what they earn.

TRY THIS
Skip it.

TIP 4

Avoid asking about relationships and children

Questions like why are you single or when will you have kids can hurt. Let people share these things when they feel ready.

TRY THIS
Wait for them.

TIP 5

Avoid asking about health

Medical details are private. If they bring it up, listen kindly, but do not dig.

TRY THIS
Respect it.

TIP 6

Avoid asking about politics and religion

These topics can divide people very quickly. Get to know someone before you share strong views.

TRY THIS
Keep it light.

TIP 7

Avoid asking why questions that sound like blame

Questions like why did you do that sound like criticism. Use what made you choose that instead.

TRY THIS
Soften it.

TIP 8

Avoid asking yes or no questions only

They end chats fast. Use how and what to invite stories.

TRY THIS
Open them up.

TIP 9

Avoid asking questions that test them

Do you know who I am or can you guess my job feel like quizzes. Be direct and kind.

TRY THIS
Be plain.

TIP 10

Replace risky questions with safe ones

Ask about hobbies, favourite foods, travel and weekends. These are warm and easy to answer.

TRY THIS
Pick safe ones.

TIP 11

Watch their face and body

If they look away or give short answers, change topic. Their body tells you when to stop.

TRY THIS
Read signals.

TIP 12

Offer something first

Share a small detail about yourself before asking something personal. Sharing builds trust.

TRY THIS
Share first.

TIP 13

Script: free time

What do you enjoy doing when you are not working? Say it warmly.

TRY THIS
Use it.

TIP 14

Script: week

How has your week been so far? Say it lightly.

TRY THIS
Use it.

TIP 15

Script: group

What brought you to this group? Say it with interest.

TRY THIS
Use it.

TIP 16

Script: hometown

Tell me about the place you grew up. Say it kindly.

TRY THIS
Use it.

TIP 17

Script: closing

Thanks for chatting with me, it was lovely to meet you. Say it sincerely.

TRY THIS
Use it.

TIP 18

Mistake: asking about age or looks in the first minute

These topics feel judging, so ask about their interests and experiences instead.

TRY THIS
Switch topic.

TIP 19

Mistake: asking why someone is single

The question can sting deeply, so wait until they choose to share this part of their life.

TRY THIS
Let them lead.

TIP 20

Mistake: comparing them with others

Comparisons make people feel measured, so avoid saying you are just like or unlike someone.

TRY THIS
Stay on them.

TIP 21

Mistake: pressing when they hesitate

Pushing after a pause breaks trust, so say no worries and move to a lighter topic.

TRY THIS
Back off kindly.

TIP 22

Mistake: asking many questions in a row

Too many questions feel like an interview, so share a little about yourself between them.

TRY THIS
Balance it.

TIP 23

Troubleshoot: when you asked something awkward

Say, sorry, that was a bit personal, and move on warmly to a lighter topic. A light recovery works.

TRY THIS
Recover lightly.

TIP 24

Troubleshoot: when they ask you a personal question

You can answer briefly or say, I would rather not say, what about you? Kind boundaries are fine.

TRY THIS
Protect yourself.

TIP 25

Troubleshoot: when you are curious about something private

Wait for trust to grow over weeks. Curiosity can wait until they offer.

TRY THIS
Be patient.

TIP 26

Troubleshoot: when culture changes the rules

Some cultures ask about family or age openly, so watch and follow local norms with care.

TRY THIS
Observe first.

TIP 27

Troubleshoot: when you cannot think of safe topics

Keep a short list of safe topics like food, travel, weekends and hobbies. Use it.

TRY THIS
Make a list.

TIP 28

Drill: list your safe topics

Write ten safe topics for first chats and keep them in your phone notes. Use one today.

TRY THIS
Write.

TIP 29

Drill: spot the risky question

Think of three questions you might ask by habit that could feel pushy, and rewrite each kindly.

TRY THIS
Rewrite.

TIP 30

Drill: practise the recovery line

Practise the line sorry, that was a bit personal aloud five times so it feels natural.

TRY THIS
Practise.

Easy things to say

When you are stuck, pick one of these. They work in many everyday friendships.

INSTEAD

“What do you enjoy doing in your free time?”

INSTEAD

“How has your week been?”

INSTEAD

“What brought you to this group?”

INSTEAD

“Tell me about your hometown.”

THANK

“Thanks for chatting with me.”

CLOSE

“It was lovely to meet you.”

Your first week

One small action a day. Each day is only a little bigger than the last.

DAY 1
Start with light topics

DAY 2
Avoid prying

DAY 3
Watch their face

DAY 4
Offer before you ask

DAY 5
Change topic kindly

DAY 6
Build trust first

DAY 7
Review how it went

Further reading

• The Fine Art of Small Talk (Debra Fine)
• How to Talk to Anyone (Leil Lowndes)
• We Need to Talk (Celeste Headlee)

The tips above are written in our own words and are general guidance. The books are suggestions for further reading.

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These lessons share general learning and everyday ideas. They are not medical or mental health advice. If you feel very anxious, low or unwell, please talk to a doctor or a qualified professional.