Ask someone out with a plan and a day

“We should hang out sometime” is easy to nod along to. Ask in one sentence with a plan and a day, then let them answer.

Get comfortable talking to people. Connsmitten is an app for building social confidence through short lessons and practice conversations, with feedback from your coach.

Turn “sometime” into a date

Ask them out in one sentence, with a plan and a day, then let them answer.

When you’re afraid they’ll say no, a hint feels obvious to you. To them it sounds like you’re being friendly. So ask in one sentence, with a plan, a day, and “with me,” so they know it’s a date. Then stop talking and let them answer. “We should hang out sometime” is a maybe nobody has to answer. “Coffee with me Saturday?” is a question they can say yes to.

Listen
Woman’s voice
Man’s voice

“That’s my stop. This was fun.”

Listen
Woman’s voice
Man’s voice

Not this: Yeah! We should hang out sometime.

This: Same. Want to get coffee with me Saturday?

Practice with a woman or a man?

At the end of a party, before they leave

Choose “A woman” or “A man” above to see the questions.

Friday night, the end of a friend’s housewarming

Listen
Woman’s voice
Man’s voice

IvyI should head out. This was so fun, talking all night.

Listen
Woman’s voice
Man’s voice

What would you say?

Listen
Woman’s voice
Man’s voice
So, um, if you ever want to, maybe we could get coffee or something? No pressure, totally fine if not.
There’s an ask in there, and the “No pressure” takes it back before Ivy can answer. Ask once, then stop.
Listen
Woman’s voice
Man’s voice
Want to get dinner with me on Tuesday?
One sentence with a plan and a day. Ivy knows what you’re asking, and all she has to do is answer.
Listen
Woman’s voice
Man’s voice
Want to get coffee sometime?
Coffee is a plan, and Ivy can agree to “sometime” without ever picking a day. Add one, and she has something to say yes to.
Listen
Woman’s voice
Man’s voice

Friday night, the end of a friend’s housewarming

Listen
Woman’s voice
Man’s voice

LukeAlright, I gotta get going. Good talking to you.

Listen
Woman’s voice
Man’s voice

What would you say?

Listen
Woman’s voice
Man’s voice
Want to go to the night market with me on Sunday?
One sentence with a plan and a day. Luke knows what you’re asking, and all he has to do is answer.
Listen
Woman’s voice
Man’s voice
Want to grab dinner Sunday? Only if you’re not busy, though.
The ask was there, and the “Only if you’re not busy” takes it back. Ask, then stop and let Luke answer.
Listen
Woman’s voice
Man’s voice
We should hang out sometime!
Luke can say “for sure” to that and never hear an ask. Name a plan and a day.
Listen
Woman’s voice
Man’s voice

Build confidence for your next conversation. Take a two-minute lesson, then have your first practice conversation with Dan.

Listen to Dan open the conversation

Hey! How was your weekend?

Dan
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Compare the two replies

“That’s my stop. This was fun.”

Listen
Woman’s voice
Man’s voice

Not this: Yeah! We should hang out sometime.

This: Same. Want to get coffee with me Saturday?

What does the second reply do that the first doesn’t?

Listen
Woman’s voice
Man’s voice
It sounds more confident.
Either one can sound confident. The second adds a plan and a day, so “sometime” becomes a question.
Listen
Woman’s voice
Man’s voice
It’s shorter.
They’re about the same length. What changed is the plan and the day.
Listen
Woman’s voice
Man’s voice
It names a plan and a day they can say yes to.
A coffee on Saturday has a yes or a no. A “sometime” is a hint they can nod along to.
Listen
Woman’s voice
Man’s voice

When they mention something they want to do

Choose “A woman” or “A man” above to see the questions.

EmmaI keep meaning to go to the outdoor movie night in the park.

Listen
Woman’s voice
Man’s voice

You: Ha, me too. I never have anyone to go with.

Is this a clear ask?

Listen
Woman’s voice
Man’s voice
A hint
That’s a hint. Emma hears that you have no one to go with, not that you want to go with her, and there’s nothing to say yes to.
Listen
Woman’s voice
Man’s voice
Clear
That one’s a hint: there’s no plan or day for Emma to say yes to. Try “Want to go with me Friday?”
Listen
Woman’s voice
Man’s voice

NathanI keep meaning to try that new escape room downtown.

Listen
Woman’s voice
Man’s voice

You: Ha, me too. You should take me sometime.

Is this a clear ask?

Listen
Woman’s voice
Man’s voice
A hint
That’s a hint. It hands the asking to Nathan, with no day, so a laugh answers it and you’re still waiting.
Listen
Woman’s voice
Man’s voice
Clear
That one’s a hint: it asks Nathan to do the asking. Try “Want to go with me Thursday?”
Listen
Woman’s voice
Man’s voice

When they say they’re seeing someone

Choose “A woman” or “A man” above to see the questions.

Sunday, after your volleyball league

Listen
Woman’s voice
Man’s voice

JuliaOh, that’s sweet of you. I’m actually seeing someone.

Listen
Woman’s voice
Man’s voice

You just asked Julia to dinner. What do you say?

Listen
Woman’s voice
Man’s voice
Oh. Is it serious?
It sounds like you’re looking for an opening. Julia answered, and a second push makes her say it again.
Listen
Woman’s voice
Man’s voice
Got it, no worries. See you Sunday?
Short and warm. Julia doesn’t have to comfort you, and Sundays stay easy for both of you.
Listen
Woman’s voice
Man’s voice
Oh no, I’m so embarrassed. Forget I said anything, I’m so sorry.
Now Julia has to make you feel better. Asking was fine. A short, warm exit lets you both move on.
Listen
Woman’s voice
Man’s voice

Sunday, after your volleyball league

Listen
Woman’s voice
Man’s voice

AndrewHa, I’m flattered. I’m seeing someone, though.

Listen
Woman’s voice
Man’s voice

You just asked Andrew to dinner. What do you say?

Listen
Woman’s voice
Man’s voice
Ha, fair enough. Still on for volleyball Sunday?
Short and easy, and it matches his light tone. Andrew doesn’t have to smooth it over, and Sundays stay normal for both of you.
Listen
Woman’s voice
Man’s voice
Oh. Is it serious?
It sounds like you’re looking for an opening. Andrew answered, and a second push makes him say it again.
Listen
Woman’s voice
Man’s voice
Oh no, I’m so embarrassed. Forget I said anything, I’m so sorry.
Now Andrew has to make you feel better. Asking was fine. A short, warm exit lets you both move on.
Listen
Woman’s voice
Man’s voice

When you find out you were at the same show

Choose “A woman” or “A man” above to see the questions.

LenaWait, you were at that show last month too? How did we not meet?

Listen
Woman’s voice
Man’s voice

Put together a reply that ends on an ask Lena can say yes to.

Listen
Woman’s voice
Man’s voice

One way to reply

  1. React to what they saidNo way, we were both there!
  2. Ask them a questionWant to get dinner with me Friday?

React to her surprise, then the plan and the day. Lena knows it’s a date, and she has one question to answer.

Listen
Woman’s voice
Man’s voice

Lines to leave out

  • We should hang out sometime. This turns the ask back into a hint. The plan and the day do the asking.
    Listen
    Woman’s voice
    Man’s voice
  • No pressure, though! It takes the ask back before Lena can answer. Ask once, then let her answer.
    Listen
    Woman’s voice
    Man’s voice

LeoHold on, you were at that show last month? I was right by the stage.

Listen
Woman’s voice
Man’s voice

Put together a reply that ends on an ask Leo can say yes to.

Listen
Woman’s voice
Man’s voice

One way to reply

  1. React to what they saidNo way, so was I!
  2. Ask them a questionWant to go to a show with me Friday?

React to the show, then the plan and the day. Leo knows it’s a date, and he has one question to answer.

Listen
Woman’s voice
Man’s voice

Lines to leave out

  • Only if you want, though! It takes the ask back before Leo can answer. Ask once, then let him answer.
    Listen
    Woman’s voice
    Man’s voice
  • We should hang out sometime. This turns the ask back into a hint. The plan and the day do the asking.
    Listen
    Woman’s voice
    Man’s voice

What the research found

People afraid of rejection thought their hints showed more interest than they did.
Vorauer, Cameron, Holmes and Pearce, Journal of Personality and Social Psychology, 2003

Your mission

Next time you want to see someone again, ask in one sentence with a plan and a day, then wait for their answer.

In the Connsmitten app

A practice conversation follows this lesson’s questions.

Build confidence for your next conversation. Take a two-minute lesson, then have your first practice conversation with Dan.

Listen to Dan open the conversation

Hey! How was your weekend?

Dan
Get started

How to talk to people