One Weird Texting Tip For All Your Date & Time Logistics

Say you’ve established that you both want to grab a drink sometime.

You: “We should grab a drink sometime when you’re free.”
Them: “Ya, I’d like that.”

Now you have to figure out date & time logistics. Which one of these texts would you send?

1. “I’m free any time after 6 on Wednesday or after 7 on Thursday. You?”
2. “When’s a good time for you?”
3. “What’s your week looking like?”
4. “How’s 7pm on Thursday?”
5. “Do Tuesday or Thursday work for you?”

Got your answer? Ok, here’s our take…

1. “I’m free any time after 6 on Wednesday or after 7 on Thursday. You?”
You’re sticking your neck out a bit too far by communicating so much new detail about your schedule with no guarantee that they’re on the same page. If they reply “I’m actually busy with work til next week”, you’ll look like you jumped the gun by giving them too much information about your schedule for this week.

2. “When’s a good time for you?”
This kind of sounds like they can dictate a choice of time, and then you’ll bend over backwards to make it work. It’s a little too submissive and powerless.

The problem is the phrase “a good time” (singular). If they reply “Friday at 5pm would work great!” and you reply that you can’t do it and suggest another time, then the submissive vibe from your original text will be gone but replaced with the awkwardness of a back-and-forth negotiation that’s more slippery than it had to be.

So “What’s a good time for you?” comes off like an inefficient, incompetent opener to the negotiation.
And a tiny part of their subconscious will wonder, why did you lead with that text when a more socially savvy person could have detected a statistical likelihood of elevated awkwardness and picked a different text?

3. “What’s your week looking like?”
This prompts them to tell you about their schedule, which is like #2 except without the submissive vibe.

When they respond with some description of their availability during this week, you should ideally be able to find some overlap with your own availability. You can expect a good chance of nailing down a mutually agreeable date & time immediately, with no backtracking. This line gives you the lowest expected awkwardness and slipperiness in the logistical negotiation, so you come off like a boss (it’s a good line to use in your business life too).

This line also has a bonus feature: it opens you up to a wide range of levels of detail in their response. Their response can range from “I have some time Friday after work.” to “Monday I’m dogsitting for my friend lol. Tuesday afternoon is looking good as long as I don’t have to work late i.e. until 7 or 8. And then Wednesday… [blah blah blah].”

It’s a very socially-savvy line for this reason. It lets you get back lots of information about them – mostly about their availability, but also potentially some tidbits about how they manage their schedule and how interested they are in you – without sticking your neck out and revealing any information about yourself. (You do reveal one thing about yourself though: how very socially savvy you are. Booya.)

Using this line is a great way to execute the Tightening Noose because the only date & time details you add to the conversation are the ones they’ll have told you are directly relevant to their logistical considerations.

4. “How’s 7pm on Thursday?”
The odds are against you that they’d want to meet you at that exact time. And when they reject that time, it leads to a prolonged negotiation.
A tiny part of their subconscious will wonder, why weren’t you savvier about maximizing the expected convenience of the negotiation when you sent your date & time text?

5. “Do Tuesday or Thursday work for you?”
Some people advise using a line like this as a happy medium between naming a specific time (#4) and letting them propose any time (#2). The idea is that it gives the other person the comfortable feeling of having some control over the situation, yet it’s a set of choices that are all good for you, and it’s giving up a sufficiently small amount of control so that you’re still the more dominant decision-maker in the relationship.

So what’s our verdict?
The truth is, none of #1-5 are bad options. In this post we’ve taken texting tips to new heights of obsessive nitpicking. But still, the winner is definitely #3:

What’s your week looking like?
This one line, including its variations like “What’s your next week looking like?”, is a rock-solid choice for 90% of the times you need to negotiate date & time logistics.