How to Ask Your Crush Out When You've Been Texting for Weeks

Ask for one specific thing at one specific time, and give him a way to answer that does not make him find the words instantly. "Are you free Thursday evening? There's a place near the station I want to take you to." That is the whole ask. Everything below is about the part that actually stops you, which was never the wording.

Ruth met Emeka in the middle of July, in the second week of an evening Italian class that neither of them was any good at. They sat next to each other because the room filled up from the back. When the course finished in August they swapped numbers in the way that usually means nothing, and this time did not, because they have been texting every day since.

Seven weeks of that now. It is September, term has started, her week is full again, and the messages have quietly flattened into how was your day. Ruth has typed a question four times. Once on the bus, twice at her desk between lessons, once at half past eleven at night, which is the worst possible time to write anything you intend to send.

She knows what she wants to say. She has not sent it.

Vagueness is the problem, not nerves

The reason the fourth draft got deleted is that it said "we should do something sometime". That sentence asks for nothing, so it cannot be answered. Emeka would reply "yeah, definitely", and both of them would be exactly where they started, except now the topic has been used up.

A question needs three things in it to be answerable: a day, a thing, and an assumption that he might say no. Give a day and you have made it real. Give the thing and he knows what he is agreeing to. Leave room for no and you have taken the pressure off, which is the only reason anybody says yes to anything.

So:

• "Are you free Thursday evening? There's a wine place by the station I've been wanting to go to and I'd like to take you."
• "I'd like to see you properly rather than keep texting you. Saturday afternoon, if you're around?"
• "This has been seven weeks of very good messages. Can I buy you dinner next week?"

Read those out loud. They are not clever. Clever is what you reach for when you are trying to make the question deniable, so that if the answer is no you can say you were not really asking. Everybody can hear that, including the person you are asking, and it makes him do the work of guessing what you meant.

Say the actual thing. It is shorter.

Now the part nobody writes about

Maybe. Not no, not yes. "That sounds nice, this month is mad though."

Here is the honest reading. Sometimes that is exactly what it says, because everybody went back to work about a week ago and September genuinely is mad. Sometimes it is a no offered gently, by someone who would rather not say the word.

You get one clarification and no more. "No problem. Is next week better, or shall I stop asking?" That gives him a clean exit and it gives you an actual answer, which is more than most people ever get. If the reply is vague a second time, take it as a no and let it go. Not out of pride. Because continuing to ask turns a nice seven weeks into something he has to manage.

And if it is a no, reply once, briefly, and mean it. "All good, glad I asked." Then leave it alone for a while. The thing Ruth is most afraid of, that it gets weird afterwards, is almost entirely within her control, and it lives in the messages she sends after the answer rather than the one she sent before it.

Sending is the hard part, and it is a real problem

Here is where advice runs out.

Ruth's question is written. It is good. It has a day in it. And the place she has to put it is a thread where the last four messages are a photograph of somebody's dog and two lines about a flat tyre, so it will arrive underneath them, at whatever moment Emeka happens to look at his phone, possibly on a platform, possibly in a meeting. Then it sits there. He has to compose a reply that matches the weight of the thing, right now, from wherever he is standing, and Ruth has to watch the read receipt while he does it.

That is not the same as being asked. That is being handed something to answer in public.

Which is the reason a written invitation still exists. You can build the invitation itself on Ask4Date and send that instead, so what reaches him is the thing you actually wrote, presented as its own page rather than as a message competing with a flat tyre, with yes and no and another day already there for him to press. He answers without having to find words. You see that it landed. Starting one takes a couple of minutes from here.

Thursday or nothing

The reason to do it this week rather than after you have thought about it more is that thinking about it more has been the activity for seven weeks. It has not produced a better sentence. It has produced a fifth draft that looks like the first four.

Pick the day. Write the twelve words, and send them before you have edited them into something that could mean anything.

Emeka already knows Ruth likes him. Seven weeks of daily messages is not subtle. The only thing the question changes is that somebody finally said it out loud, and asking is the only version of this that ends with an answer.