What to do when he keeps saying maybe instead of yes

Pay attention to what follows the maybe. If he names a day, asks what you are doing, or offers a different night, the maybe is about timing and he is still in. If the maybe comes back every time you propose something, with no counter offer and no new day, he is keeping options open without committing to you.

Look at how specific he is. Vague lines like we'll see or I'll let you know usually mean he has not decided whether he wants to spend time with you. A maybe that includes a real reason, like a shift that ends at nine, is more likely to become a yes if you leave him room to fit it in.

Also check the gap between messages. Someone who is into you but busy will usually still reply the same day. Someone who waits three days to say maybe is showing you how much space you currently have in his week.

A good reply here makes one specific offer, not an open question. What are you up to gives him homework. A day, a place, and a rough length give him something he can accept in one word. Keep it short enough that saying yes costs him almost nothing.

Acknowledge the maybe without poking at it. You are not asking him to justify his hesitation. Treat it as normal, then move straight to the next step. That keeps him from feeling cornered, which is often why people keep saying maybe in the first place.

Leave a real alternative too. Offer a second option, like a different night or a shorter coffee instead of dinner. A choice between two plans is easier to answer than a yes or no about one plan he is already unsure of.

Send one follow up after the maybe, and wait a day or two rather than sending it the same night. If he answers with a specific day or time, confirm it and move on. If he says maybe again, accept that as his answer for now and do not send a third message asking.

Match the window to the plan. For a weekday drink, a day of silence is normal. For a weekend plan, if he has not picked a day by Thursday, it probably is not happening. Waiting past that point turns your attention into a test he never agreed to take.

Stop when the pattern repeats. If he has said maybe to two or three specific offers and never proposed a plan himself, close the loop with a short message that says you are not going to keep planning around it. Then it is on him to come back with a real day, or not.