The hardest part of a lot of friendships is one sentence long. You’ve had the same friendly chat with someone at the gym a dozen times. You get on well with the new person in the other team. Your neighbour seems great. And every time, the moment to say “do you want to grab a coffee some time?” arrives and passes, because it feels like it might be weird.
It almost never is. Here’s why, and exactly what to say.
Why it feels riskier than it is
Psychologists have spent years measuring how badly we predict other people’s answers, and the mistakes all lean the same way.
We expect a no far more often than we get one. In a 2008 set of studies in the Journal of Personality and Social Psychology, Francis Flynn and Vanessa Lake had people ask strangers for small favours, after first guessing how many they would need to ask. People consistently underestimated how many would say yes, in some studies by as much as half. The researchers’ explanation is worth remembering: we think about how awkward it is to ask, and forget how awkward it is to say no.
We think we came across worse than we did. A 2018 paper in Psychological Science by Erica Boothby and colleagues called this the liking gap. After a conversation with someone new, people consistently believed their partner liked them less than the partner actually did. It showed up between strangers in a lab, among first-year students getting to know their housemates, and in a community sample, and in the student study it lasted for months.
We underestimate how much a message means. In 2022, researchers led by Peggy Liu found that people who reached out to someone they hadn’t spoken to in a while underestimated how much it was appreciated, and the more of a surprise the message was, the bigger the gap.
Put simply: the person you want to ask probably likes you more than you think, is more likely to say yes than you think, and will be more pleased to be asked than you think.
What actually makes an ask weird
When an invitation does land awkwardly, it’s usually for one of four reasons, and all of them are fixable.
It’s vague. “We should hang out some time” puts all the work on the other person and almost never turns into anything.
It’s too big. Dinner, a whole Saturday, or meeting your friends is a lot to say yes to with someone you don’t know well yet. A coffee is small on purpose.
The reason is unclear. If someone can’t tell whether you’re asking as a friend, a colleague or a date, they’ll fill in the gap themselves, and not always the way you meant.
It’s hard to say no. Cornering someone in front of others, or asking three times, turns an invitation into pressure.
The shape of a good ask
Almost every good invitation has the same four parts: a reason, a small specific plan, a time, and an easy way out.
“I’ve really enjoyed our chats after class. Want to grab a coffee after Thursday’s session? No worries if you’re flat out.”
The reason tells them why you’re asking. The plan tells them what they’re agreeing to and roughly how long it will take. The time makes it real. And the easy out tells them a no won’t cost anything, which, as Flynn and Lake found, is exactly what people worry about when they’re asked.
What to say, person by person
A colleague
Work gives you the easiest reason there is, so use it.
“I’d love to hear more about how your team works. Want to grab a coffee downstairs one morning this week?”
For someone new, make it a welcome: “How are you finding it so far? Let me buy you a coffee and give you the unofficial tour.” Keep it in work hours the first time, and it reads exactly as it’s meant.
A neighbour
Neighbours are easiest to ask in person, on the footpath, while you’re already chatting.
“We keep having these chats over the fence. Do you want to walk down to the café on Saturday morning?”
A café you both already walk past takes all the planning out of it.
Someone from the gym, a class or a club
You already have a regular time and place in common, so attach the coffee to it.
“A few of us are getting a coffee after Sunday’s run. Want to come?”
Or one-on-one: “Coffee after the session on Thursday? I’ve been meaning to ask how you got into it.” Straight after the class or session works well, because neither of you has to make a special trip.
A friend of a friend
The mutual friend is your reason, and sometimes your introduction.
“Sam said we’d get on, and after Saturday I think Sam was right. Coffee one weekend?”
If you only met once at a party, a message within a few days works better than one a month later. The conversation is still fresh for both of you.
An old friend you’ve lost touch with
This is where the Liu research matters most. The longer it’s been, the more it feels like you need an excuse, and the more the message is likely to mean to them.
“I drove past our old café today and thought of you. It’s been far too long. Coffee soon? I’m free most mornings next week.”
You don’t need to explain the gap or apologise for it. Just pick it back up.
Someone more experienced you’d like to learn from
Be specific about what you’d like to ask, and generous with their time.
“I’m thinking about moving into product design, and I’d love to hear how you made the switch. Could I buy you a coffee for half an hour, any time in the next few weeks?”
There’s more on this in how to find a mentor, and how to actually ask.
Someone you’d like to date
Coffee is a great first date, but don’t disguise one as something else. Being clear is kinder, and it’s easier to say yes to.
“I’ve really liked talking to you. Would you like to get a coffee with me, as a date?”
If the answer is no, you’ve lost nothing but a moment of awkwardness, and you’ve both been spared weeks of guessing.
In person or by message?
If you can ask in person, do. In a 2017 study, Mahdi Roghanizad and Vanessa Bohns had people ask strangers to fill in a short survey, either face to face or by email, using exactly the same words. The in-person requests got far more yeses, yet the people asking expected email to work about as well. A message from someone a stranger can’t see is easy to ignore. A friendly face is not.
With people you already know, a text is fine. But if you’re going to see them anyway, the café after class or the chat at the office kitchen is the best moment you’ll get.
If they say no, or don’t reply
A no is usually about their week, not about you. “Not this week” often means exactly that, so it’s fine to try once more a few weeks later. If there’s no reply at all, one light follow-up is plenty: “No stress if this got buried, the offer’s open.” After that, let it go, and keep being friendly when you see them. Plenty of coffees happen months after the first ask, when the other person reaches out instead.
And if they say yes, the coffee itself is the easy part. Make it about an hour, somewhere you can hear each other. If you’re worried about the conversation, here’s what to talk about in a first coffee.
Or skip the ask altogether
Flat White takes care of the hardest sentence for you. We match you with one person who has also said they’d like to meet someone new, for friendship, networking, a mentor or a date, and book the two of you a table at a café for an hour. Nobody has to work up the nerve, because you’ve both already said yes. We’re opening across Australia city by city, and joining the waitlist moves your city closer to the front.
An hour, a coffee, someone new.
No awkward ask required. Join the waitlist at joinflatwhite.com →