LESSON 37 · HOW TO APPROACH SOMEONE

Suggest Meeting Again Casually

Thirty easy ways to suggest meeting again casually, so a nice chat turns into a second hello.

Keep it casual. Ask while it feels good.

28 tipsEasy things to say7-day plan

28 tips that really help

These ideas come from How to Win Friends and Influence People (Dale Carnegie), The Like Switch (Jack Schafer), The Charisma Myth (Olivia Fox Cabane), and everyday practice. Pick one tip and try it today.

Photo for the tip: Why ask casually
TIP 1

Why ask casually

People like clear and easy invites. A casual suggestion turns a nice chat into the start of a friendship.

TRY THIS
Ask.
Photo for the tip: End on a high note
TIP 2

End on a high note

Ask while the mood is warm. Do not wait.

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Ask now.
Photo for the tip: Mention something you enjoyed
TIP 3

Mention something you enjoyed

Say, I enjoyed talking about hiking. Warm opening.

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Mention it.
Photo for the tip: Suggest a small plan
TIP 4

Suggest a small plan

Coffee, a walk or a lunch. Small plans feel easy.

TRY THIS
Suggest small.
Photo for the tip: Name the activity
TIP 5

Name the activity

Shall we grab coffee sometime? Clear is kind.

TRY THIS
Be clear.
Photo for the tip: Offer a rough time
TIP 6

Offer a rough time

Maybe next week? Gives direction without pressure.

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Offer a time.
Photo for the tip: Ask for contact details
TIP 7

Ask for contact details

Can I get your number? Easy and natural.

TRY THIS
Ask it.
Photo for the tip: Use a shared hook
TIP 8

Use a shared hook

I will message you about that event. A link makes sense.

TRY THIS
Use a link.
Photo for the tip: Keep it light
TIP 9

Keep it light

No pressure, only if you want. Easy to answer.

TRY THIS
Add it.
Photo for the tip: Follow up within two days
TIP 10

Follow up within two days

Send a short message soon. Keep the warmth.

TRY THIS
Message soon.
Photo for the tip: Make it specific in the message
TIP 11

Make it specific in the message

Suggest a day and place. Specific plans happen.

TRY THIS
Be specific.
Photo for the tip: Script: suggesting
TIP 12

Script: suggesting

Shall we grab coffee sometime this week? Say it lightly.

TRY THIS
Use it.
Photo for the tip: Script: contact
TIP 13

Script: contact

Can I get your number so I can message you? Say it kindly.

TRY THIS
Use it.
Photo for the tip: Script: link
TIP 14

Script: link

I will message you about that event. Say it easily.

TRY THIS
Use it.
Photo for the tip: Script: easy
TIP 15

Script: easy

No pressure at all, only if you would like to. Say it warmly.

TRY THIS
Use it.
Photo for the tip: Script: closing
TIP 16

Script: closing

It was lovely to chat, see you soon. Say it gladly.

TRY THIS
Use it.
Photo for the tip: Mistake: waiting too long
TIP 17

Mistake: waiting too long

Warmth fades, so ask on the day.

TRY THIS
Ask soon.
Photo for the tip: Mistake: being vague
TIP 18

Mistake: being vague

Maybe sometime rarely happens, so name a plan.

TRY THIS
Name a plan.
Photo for the tip: Mistake: making it too big
TIP 19

Mistake: making it too big

Big plans scare people, so keep small.

TRY THIS
Keep small.
Photo for the tip: Mistake: apologising for asking
TIP 20

Mistake: apologising for asking

Sorry weakens an invite, so ask gladly.

TRY THIS
Ask gladly.
Photo for the tip: Troubleshoot: when they say maybe
TIP 21

Troubleshoot: when they say maybe

Say, great, I will message you, and follow up. Light.

TRY THIS
Follow up.
Photo for the tip: Troubleshoot: when they say no
TIP 22

Troubleshoot: when they say no

Say, no problem, it was nice to meet you. Kind.

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Stay kind.
Photo for the tip: Troubleshoot: when you forget to ask
TIP 23

Troubleshoot: when you forget to ask

Message them within a day and say it was nice. Still works.

TRY THIS
Message.
Photo for the tip: Troubleshoot: when they do not reply
TIP 24

Troubleshoot: when they do not reply

Wait a week and send one gentle follow-up. Then let go.

TRY THIS
Follow up once.
Photo for the tip: Troubleshoot: when you feel nervous
TIP 25

Troubleshoot: when you feel nervous

Practise the line once, breathe and ask. Brief.

TRY THIS
Breathe.
Photo for the tip: Drill: write your invite line
TIP 26

Drill: write your invite line

Write two invite lines and say them aloud. Ready.

TRY THIS
Write them.
Photo for the tip: Drill: ask one person this week
TIP 27

Drill: ask one person this week

Ask one new person to meet again. Do it.

TRY THIS
Ask.
Photo for the tip: Drill: send a follow-up
TIP 28

Drill: send a follow-up

Send one friendly follow-up message today. Warm.

TRY THIS
Send it.

Easy things to say

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

SUGGEST

“Shall we grab coffee sometime?”

SHARE

“Can I get your number?”

LINK

“I will message you about that event.”

EASY

“No pressure, only if you want.”

CONFIRM

“Great, see you then.”

CLOSE

“It was lovely to chat.”

Your first week

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

DAY 1
End on a high
DAY 2
Suggest a plan
DAY 3
Swap contacts
DAY 4
Keep it light
DAY 5
Confirm
DAY 6
Message soon
DAY 7
Meet

Further reading

  • How to Win Friends and Influence People (Dale Carnegie)
  • The Like Switch (Jack Schafer)
  • The Charisma Myth (Olivia Fox Cabane)

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.

More lessons in “How to Approach Someone”

Keep going. Small steps every day make a big change.

← Previous: Exit Gracefully if It Is Not ClickingNext: Handle a Cool Reception Without Hurt →

  1. What You Are Really Afraid Of
  2. Most People Are Glad You Spoke First
  3. The Spotlight Effect at Parties
  4. A Rejection Is Rarely What You Imagine
  5. Why Waiting Makes It Harder
  6. Reframe Approaching as Being Kind
  7. The Worst Realistic Outcome Is Small
  8. Spot Open and Closed Signals
  9. The Right Moment to Say Hello
  10. Approach Alone, Pairs and Groups Differently
  11. What to Do When They Look Busy
  12. Wait for the Natural Pause
  13. Notice Who Is Standing Alone
  14. Be Respectful if It Is Not the Time
  15. Smile Before You Speak
  16. Walk Over at an Angle, Not Straight On
  17. Keep Open and Relaxed Posture
  18. The Friendly Introduction Handshake
  19. Eye Contact That Feels Warm
  20. Say Your Name With a Smile
  21. Do Not Hover: Commit to Hello
  22. Comment on the Shared Situation
  23. Ask for a Small Opinion
  24. Give a Genuine Compliment
  25. Ask for a Small Favour
  26. Introduce Yourself Simply
  27. The Question That Starts Any Chat
  28. Use Humour Lightly
  29. Approach at a Party
  30. Approach at Work
  31. Approach in Class
  32. Approach at the Gym
  33. Approach Online First
  34. Approach a Neighbour
  35. Keep the Chat Going for One More Minute
  36. Exit Gracefully if It Is Not Clicking
  37. Suggest Meeting Again Casually
  38. Handle a Cool Reception Without Hurt
  39. Reflect and Learn After Each Approach
  40. Practise Approaching Every Week
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