Sir Said Maybe Later and Madam Kept Her Whole Evening Free
A man can occupy an entire evening without technically making a single plan.
It usually begins with something wonderfully vague. “Maybe around eight,” he says, or, “I should be free later.” You ask what he has in mind, and Sir tells you he will let you know.
Lovely.

Now you have a choice. You could make other plans, meet a friend, go out for dinner or simply decide that “maybe later” is not enough to claim several perfectly good hours of your life.
But you leave the evening open for him anyway. He might be free, after all, and somehow that is enough to make every other possibility feel a little premature.
And eight is not terribly far away, is it? You like him and would like to see him. Leaving the evening clear feels completely reasonable.
So that is exactly what you do. You deliberately protect several hours for a plan that does not actually exist yet. Which, when you think about it, is remarkably similar to accepting a delivery window.
Something may be coming, but nobody can tell you exactly when. Yes, exactly.
Your Evening Is Currently Out for Delivery
At six, this feels entirely sensible. You get ready slowly, pour yourself something nice and consider dinner, although dinner is suddenly complicated because perhaps you are going to dinner, and it would be unfortunate to ruin dinner with dinner.
Around seven, Sir is “just finishing something.”
Fair enough. Nobody expected a trumpet fanfare at precisely eight.
Then a friend asks whether you fancy a drink. Under ordinary circumstances, you probably would. But tonight you decline because Sir may become free, and there we have it: a perfectly real invitation has now lost to the possibility of one.
You finish getting ready anyway, which leaves you looking lovely in your own home with nowhere in particular to go.
When somebody asks what you are doing tonight, you say, “I might be seeing someone later,” giving the whole affair a degree of organization it has not remotely earned.
By eight, the evening has become rather peculiar. Nothing is happening, but you do not want to begin anything else because something still might.
And you are not exactly waiting, you are simply beautifully available.
The Window Keeps Moving
Then comes the update.
“Running a little behind.”
Behind what is difficult to say, since nobody ever named an actual time, but we shall not become tiresome over details. You simply decide to keep the evening open a little longer, because surely Sir cannot be too far away now.
And this is where the delivery-window arrangement starts showing its true talent. It does not need to steal four hours from you all at once. It takes twenty minutes, then another half hour, then “soon.”
Each little extension seems harmless enough, so you make the same decision again and again: fine, give it a little longer.
Dinner remains unsettled because he may suggest dinner. Other plans stay off the table because he may call. Somewhere along the way you find something tiny to eat, something decorative that succeeds mainly in making you much more interested in proper food.
Still, nothing has technically gone wrong, which is almost the impressive part. Nobody has canceled on you because nobody ever quite made plans with you in the first place.
A man does not need to make plans when you are willing to keep the evening free anyway
Alexandra
By nine, something rather magnificent has happened: Sir still has not made a plan, yet your evening has somehow become completely unavailable.
Nothing is happening, but nothing else has been allowed to happen either.
A real invitation came and went. Dinner became theoretical. Several perfectly good hours disappeared while you kept yourself free for the possibility that he might eventually decide what the two of you were doing.
And goodness, once you look at the whole evening, it is quite a picture. Your makeup is done, your handbag is ready, you’re very hungry, an actual menu would now be delightful, and still nobody has named a place.
Poor Madam.
She has given an entire evening to something that has yet to earn the dignity of becoming a plan.
Then Sir Checks Whether You Are Still Available
Eventually, your phone lights up, and for one delicious second the whole evening appears to have been vindicated.
Then you open the message.
“What are you doing?”
Excuse me? What are you doing??
Madam has spent several hours making absolutely certain she was doing nothing.
Sir, meanwhile, may be genuinely puzzled by your reaction. He never asked you to wait. He said he might be free. He did not tell you to decline your friend, postpone dinner or preserve the entire evening in case he suddenly developed a plan.
And, annoyingly, he is not entirely wrong. You did that part yourself.
He offered you nothing more than a vague possibility, and because you wanted to see him, you somehow gave it the whole evening. No restaurant, no time, not even a definite yes—just “maybe later".
Sir left the evening vague, and Madam somehow responded by keeping the whole thing free for him.
And by the time he finally became available, he had already had several hours of your night without taking you anywhere.

Continue reading
A few more thoughts on love, dating, and everything in between
A little more support
If your situation feels too specific for generic internet advice, talking it through with a professional can help. BetterHelp offers online counseling with licensed therapists, so you can get support from wherever you feel most comfortable.
Explore online counseling →I may earn a commission if you use my BetterHelp link, at no additional cost to you.
From Alexandra’s bookshelf
What to do when he... top 100 questions answered.
Explore the book →