The honest answer first: you cannot make him ask. You can make it easier, and you can make it obvious, and after that it is still his move and it may never come. The thing that reliably works is the one nobody wants to hear, which is that you ask him.
That is not a consolation prize. The person who names a day is the person who finds out.
What hinting actually does
Hinting is not useless. It just does a smaller job than people think. Standing a bit closer, remembering what he said last week, laughing at the thing that was only slightly funny: all of that tells him you like talking to him. It does not tell him you want to go somewhere with him on a Saturday. Those are different pieces of information and he is not going to risk the first one to test the second.
If you want to give signalling its best shot, give it something to work with:
Say a specific thing you like. "You're funny" is a hint. "I look forward to Tuesdays because you're in" is nearly a sentence.
Mention something you want to do, out loud, in front of him. Not as an invitation. As a fact about your week.
Stay a minute longer than you need to. The conversation after the reason for the conversation has ended is the one that counts.
Give that two or three weeks. If nothing has happened by then, you have your answer about hinting, and you still have the other option.
Why he might not ask
Some people do not ask. Most of the reasons sit with him rather than with you. He might think you are seeing someone. He might think asking at work is a bad idea. He might be nineteen and have never done it before and be waiting for a version of the moment that does not exist.
None of that gets solved by you waiting more patiently.
Keziah and the trade counter
Keziah is nineteen, second year of her apprenticeship at a four-ramp garage on an industrial estate. Theo is twenty and drives the parts van from the motor factors. He is in twice a day, morning and mid-afternoon, and has been since February.
She knows he supports a team that never wins. He knows she is saving for her own car and that the one she has is held together by optimism. They have talked every working day for eight months and none of it has left the trade counter.
It is October now and the roller door is open and the yard is freezing. He comes in with a box of brake pads, puts it down, waits for the signature. There is maybe forty seconds of this. She has spent weeks making the forty seconds as good as she can make them and he has still never said anything about a Saturday.
So one Thursday she stops trying to engineer it. She signs the sheet, hands the clipboard back and says: "There's a thing on at the Forum on Saturday. Do you want to come with me?"
He says what? She says it again. He says yeah, alright. Then he picks up his empty crate and goes, because he has eleven more drops, and she stands there holding a pen.
That is what it looks like. Not a speech. Eleven words and a bit of a stomach drop.
The sentence, and the two things in it
Whatever you say needs two things in it, and almost nothing else.
A day. "Sometime" is where invitations go to die. Saturday. Thursday after your shift. Next Friday.
A thing. It does not have to be impressive. It has to be real enough that he can picture being there.
So: "Do you want to go to the car show at the showground on Sunday?" Or: "I'm going to the thing at the Forum on Saturday, come with me." Or, if the word is the point and you want it to be: "Do you want to go out on Saturday? Like, out out."
That last one is scarier and clearer. Pick based on whether you would rather risk the awkwardness or risk the ambiguity.
What to do about the maybe
No is survivable. You already know this, even if it does not feel like it. He says sorry, you say no worries, and then you both carry on doing your jobs, and it is strange for about a week and then it is not.
Maybe is harder. "I'll let you know" and "I might be working" and "yeah, maybe sometime" all leave you exactly where you started, except now you are also waiting.
Give maybe one follow-up and no more. A day or two later: "Still up for Saturday?" If the answer is another maybe, treat it as a no and stop carrying it around. You are allowed to stop. That is the whole point of asking instead of hinting: you get to find out and then you get your head back.
The part where you actually send it
Saying it out loud is one route. If the forty seconds at the counter is never going to be enough, or if your voice does something unhelpful when you are nervous, the other route is sending it, and sending it is where people stall. You write it. You read it back. It looks too keen, or too casual, and then you leave it in the box and nothing happens.
The problem with a text is that it lands in the middle of everything else and it asks him to compose a reply, which is a job, and jobs get postponed. You can build the invitation itself on Ask4Date instead, so what reaches him has the day and the thing already in it and an answer he can give by pressing it, and you can see that it was opened. Writing it once and sending something finished is easier than drafting a message eleven times.
The reason to move now is not that there is a deadline. It is that there isn't one, and a thing with no deadline can be put off until March.
You already know who he is. You already know which day would work. The only part left is the sending, so pick the day, write the line, and get it out of your hands tonight.
