How to Ask a Guy Out: A Story About Making the First Move

How to ask a guy out, in one sentence: send a specific message that says what, when and roughly how long, and give him an easy way to say no. That's it. Same as anyone asking anyone. The hard part was never the wording. It's the half hour before you hit send, when your brain keeps asking, "Is this going to look desperate?"

So here's a made-up story about a woman named Nora. We'll walk through it, look at what was going on at each turning point, and then replay it with different choices.

The story says "he," since that's who Nora's asking. Swap in whoever you like. The steps don't change.

Wednesday, 10:30 p.m.

Nora is 29 and works in marketing. Two weeks ago a friend dragged her to trivia night at a neighborhood bar, and she ended up on a team with Sam. They came in second to last, mostly because neither of them could answer a single sports question, and they laughed through the whole thing. They swapped numbers on the way out.

Since then they've texted most days. He asks how her big presentation went. He sends photos of the questionable lunch specials at his office cafeteria. He remembered that she hates cilantro. Last week he mentioned, offhand, "I keep walking past that dumpling place on Fifth and the line is always insane. One day."

Wednesday, 10:30 p.m. Nora's on the couch, phone in hand, staring at that text. She wants to ask him. Then the voice shows up: "If I ask first, will he think I'm desperate? Too eager?"

So she does what everyone does and searches it. The first post she finds insists men lose interest the second a woman makes the move. The next is a Reddit thread full of guys saying they'd love to be asked out and it basically never happens. Now she's more confused than before she looked.

Three drafts, two deleted

Draft 1: "Craving dumplings so bad lately"

She knows what this is: bait for him to do the asking. The problem is that if he just replies "same, they're so good," she learns nothing. Not interested? Didn't catch it? Deleted.

Draft 2: "What are you up to this weekend?"

Looks direct. Says nothing. He has to report on his whole weekend before he knows why she's asking, and if he says "helping my brother move Saturday, why?" she still has to ask him out, now with more pressure. Deleted.

Draft 3:

"You said you've been wanting to try that dumpling place on Fifth. Want to go with me? I'm free Thursday after work or Saturday afternoon, probably an hour or so. If you're busy or not into it, totally fine, just tell me."

She reads it under her breath twice. What, two times to pick from, how long, and an out. And it sounds like her.

After she hits send

10:52 p.m. Sent. She puts the phone face down on the couch cushion and goes to wash her face.

Over the next fifteen minutes she checks it four times. Read 10:58 PM. No reply. She starts second-guessing: was "totally fine" too much? Should she have offered just one time?

11:20 p.m. The phone lights up.

Two endings

Ending A: he says yes.

"Yes! Saturday works. Anytime after 3"

Nora replies:

"Saturday at 3:30, meet out front?"

That's the whole thing. She doesn't follow it with three more texts and a row of exclamation points, and she doesn't ask "so is this like a date date?" Friday evening she sends a quick "See you tomorrow at 3:30!", a light confirmation that also gives either of them an easy chance to reschedule.

Ending B: he says no.

"Ahh this week's kind of crazy for me, probably can't, sorry"

No other time. Nora's stomach drops. She types "Is it because you don't want to go out with me?" Then she deletes it and sends:

"No worries at all, hope the week calms down!"

And then she actually stops. No "what about next week?" the next morning. No asking their mutual friend whether he's seeing someone. When he texts Thursday about the cafeteria's mystery meatloaf, she answers like normal. Not colder, not performing how fine she is.

If Sam comes back later with "hey, still up for those dumplings?", he's picked it back up. If he doesn't, she has her answer, and she doesn't have to keep guessing.

There are two other common replies. "Out of town this weekend, but how about Tuesday?" is great news. He offered his own time, so take it. "I should mention I've been seeing someone" gets "Got it, thanks for telling me," and that's the end of it.

Will asking a guy out make you look desperate?

Here's the thing: asking isn't what looks desperate. What comes after can. Texting three more times. Pushing for a reason. Hinting that he owes you an explanation. Coming back three days after a no with a new activity.

A specific invite with a real out says the opposite. It says: I know what I want, and you're allowed your own answer. That reads as confident. If the bigger question of whether you should make the first move at all is what's nagging you, our piece on making the first move covers it. This one is just about how.

Back to Nora. Each turning point has a bit of psychology in it:

• When she hesitated, she was handing the vote on "should I ask him?" to strangers online. They'll argue about it forever. The only person who can tell her what Sam thinks is Sam.
• She deleted Draft 1 because a hint that doesn't land gives you zero information. Only a specific invite shows you where someone stands. That's the point of our free lesson on a specific invite: telling a real plan apart from "we should hang out sometime."
• She deleted Draft 2 because "are you free?" makes him hand over his schedule before he knows what you're asking. Giving two times to choose from does half the deciding for him, which is what our lesson on how to offer three options practices.
• She flipped her phone over because staring at "Read 10:58 PM" only feeds the story in your head. For what to do with that waiting feeling, see left on read.
• She deleted "Is it because...?" because that line makes him defend his answer. Taking it at face value is what lets two people keep talking normally afterward.

The same story, different choices

If she'd sent Draft 1: Sam replies "same, they're so good," and the conversation drifts back to cafeteria food. Nora lies awake wondering whether he wasn't interested or just didn't get it. That question could follow her around for weeks.

If she'd sent Draft 2: Sam says "helping my brother move Saturday, why?" Now she has to build the invite from scratch right after he's told her Saturday's out. One message turns into three rounds of back-and-forth, each more awkward than the last.

If she'd sent the "is it because" text: Sam has to explain that no, really, he's just slammed. They both feel weird. The next conversation has a little extra caution in it.

If she'd never asked and waited for him: that's a choice too, and not a wrong one. It just means the only person deciding whether you two ever get dumplings is him.

Whichever ending Nora got, she got an answer, and nobody had to feel embarrassed. That's what a good first move looks like. If you want to write one for your own situation, our interactive lesson making the first move is great walks you through it. More on texting and asking people out lives on our texting topic page.

FAQ

What should I do if a guy says no when I ask him out?

Send something easy like "no worries!" and stop there. Don't ask why. Treat him normally afterward: no avoiding him, no big show of being fine. A no is about this invite and these two people, not about you.

If I ask him out, do I pay?

You can plan to cover it since you asked, or say up front, "Let's split it." What matters is deciding your approach ahead of time so you're not doing the awkward dance when the check comes. Who pays on a first date covers more scenarios.

He said yes but never locks in a time. Now what?

Give him two specific options: "Saturday at 3 or Sunday afternoon?" If it's still "either works, we'll see," treat it as a yellow light and let the next move be his.

Do I need to know he likes me before I ask him out?

No. Asking is one of the ways you find out. Whether he says yes, and whether he offers his own time if he can't make yours, tells you more than a hundred rounds of guessing. If you want to read his signals first, see signs he likes you.