Making Friends / How to Start a Conversation / Lesson 32

LESSON 32 · HOW TO START A CONVERSATION

When They Are Shy Too

Thirty-two easy ways to help when they are shy too, because two shy people can make wonderful friends.

Shy plus shy can be sweet. Go gently together.

29 tipsEasy things to say7-day plan

Start with tip 1

Jump to the 7-day plan

29 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

Two shy people can connect

When both people are nervous, honesty and gentleness can make a close bond quickly. Shared shyness is a bridge.

TRY THIS
Be gentle.

TIP 2

Smile warmly

A friendly smile puts shy people at ease. Start there.

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Smile.

TIP 3

Admit your own shyness

Say, I am a bit shy too. This relaxes both of you at once.

TRY THIS
Say it.

TIP 4

Ask easy questions

Choose simple questions like what brought you here? Easy topics lower pressure.

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Ask.

TIP 5

Share small things

Small shares like your favourite tea invite them to share too.

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Share.

TIP 6

Go slowly

Do not rush. Short chats now can grow into longer ones later.

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Be patient.

TIP 7

Do something together

Walks, crafts or games give you something to do with your hands and eyes. Activity eases talk.

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Do something.

TIP 8

Use text as a bridge

Shy people often open up in messages first. Send a friendly note afterwards.

TRY THIS
Message.

TIP 9

Respect silences

Quiet is okay between shy friends. Smile in the pauses.

TRY THIS
Enjoy quiet.

TIP 10

Offer clear plans

Say, shall we get coffee on Saturday at ten? Clear invites help shy people say yes.

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Be specific.

TIP 11

Avoid pressure

Do not push for deep sharing too fast. Let trust grow.

TRY THIS
Go gently.

TIP 12

Celebrate small steps

Notice and thank each other for trying. Small wins build confidence.

TRY THIS
Celebrate.

TIP 13

Script: admitting

I am a bit shy too, so I hope that is okay. Say it warmly.

TRY THIS
Use it.

TIP 14

Script: inviting

Would you like to sit together for a bit? Say it gently.

TRY THIS
Use it.

TIP 15

Script: sharing

Starting chats is hard for me, but I am glad we are talking. Say it honestly.

TRY THIS
Use it.

TIP 16

Script: plan

Shall we get coffee on Saturday at ten? Say it clearly.

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Use it.

TIP 17

Script: closing

Thanks for chatting with me, that was easier than I thought. Say it sincerely.

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Use it.

TIP 18

Mistake: expecting them to lead

Shy people may wait, so take a small lead.

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Start gently.

TIP 19

Mistake: mistaking shyness for dislike

Quiet people often care deeply, so be kind.

TRY THIS
Stay warm.

TIP 20

Mistake: asking big personal questions

Shy people need time, so start light.

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Go light.

TIP 21

Mistake: giving up after one try

Shy friends need repeat contact, so try again.

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Keep trying.

TIP 22

Troubleshoot: when you both freeze

Laugh lightly and say, we are quite a pair. Humour helps.

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Laugh together.

TIP 23

Troubleshoot: when they hardly answer

Keep your warmth and try a different topic. Some need time.

TRY THIS
Be patient.

TIP 24

Troubleshoot: when you feel awkward

Remember they feel it too. Smile and slow down.

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Slow down.

TIP 25

Troubleshoot: when in a group

Move to a quieter corner together. Small spaces help.

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Find a corner.

TIP 26

Troubleshoot: when you want to see them again

Send a short message with a clear plan. Written invites can be easier.

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Send a plan.

TIP 27

Drill: say I am shy too

Practise saying I am shy too with a smile in a mirror. Use it once.

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Practise.

TIP 28

Drill: invite one shy person

Invite one quiet person for a coffee this month. Keep it simple.

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Invite.

TIP 29

Drill: send a gentle text

Send a gentle text after a chat with a shy person. Notice the warmth.

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Message.

Easy things to say

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

SMILE

“Hi, I am a bit shy too.”

ASK

“Would you like to sit together?”

SHARE

“Starting chats is hard for me.”

OFFER

“We can take it slowly.”

THANK

“Thanks for chatting with me.”

CLOSE

“That was easier than I thought.”

Your first week

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

DAY 1
Smile warmly

DAY 2
Admit shyness

DAY 3
Ask easy questions

DAY 4
Share small things

DAY 5
Go slowly

DAY 6
Do something together

DAY 7
Follow up

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.