Is He Interested If He Won't Make Plans Ahead?

Start by separating two things that look alike in a text thread. One is a guy who's bad at committing to a time until the day arrives. The other is a guy who's steering away from anything with a fixed date. The first still answers a concrete option with a concrete answer, even if it's "Thursday works, can I confirm Wednesday morning?" The second keeps replying with "maybe", "we'll see", or "let me check my week" and never comes back to the question. Look at what happens when you ask something specific. If the chat stays warm but the plan keeps dissolving, he likes talking to you more than he wants to see you, at least for now. If he takes the specific question seriously and gives you a yes, a no, or a counter-offer, the planning problem is probably logistics, not interest. Also notice whether he starts any part of the exchange himself. A guy who asks you questions, remembers what you said, and brings up things from earlier is spending attention even if he never sets a date.

A plan that works with someone who keeps things loose has three parts: a day, a place, and a reason tied to something you already talked about. "Thursday, that bar you mentioned with the good mezcal" gives him an easy yes, and it shows you were listening. Don't offer two or three options and ask him to pick. That hands the work back to him and invites another round of "depends". Keep the window small. An evening after work is easier to say yes to than a whole weekend. Make saying yes cheap and saying no just as easy, so his answer is honest. If he declines, offer one alternative with a different day and don't argue for the first one. A single counter-proposal tells you a lot. If he sends a real alternative, he's trying. If he turns down the second option too without suggesting anything, stop escalating and let the question rest.

Timing matters more than the wording. Send the concrete plan in the afternoon or early evening, when people are looking at their week, not late at night when a plan feels like pressure. If he doesn't answer within about a day, send one short follow-up that restates the plan without guilt, like a reminder of the day and place. If that also gets no reply, wait two or three days before trying again. Don't send a string of messages, and don't check whether he's online. If the second attempt goes nowhere and the chat has gone thin, stop pursuing the plan and let the conversation end on its own. A few weeks of this pattern with no concrete yes is your answer. If he suggests something real later, you can respond then, but don't keep the door open on the assumption that next week will be different.