Reply to 'wanna grab a drink sometime' and get a real date

Read the word sometime as a question he hasn't asked yet. He's checking whether you want to meet, and he's leaving room to back out if you don't. That isn't a bad sign on its own. It just means the ball is in your court, and if you let it sit, it will drop.

Look at how the conversation has gone before this. If you've been trading messages for days with real follow-ups, the invite is probably sincere but cautious. If his replies have been short and this came out of nowhere, he may be testing whether you'll come along or just being polite. The invite itself won't tell you which. The effort he's put into the thread will.

Your reply should accept or decline, then hand him something specific. Pick a window that's close enough to feel real, like a weeknight or the coming weekend, and name it in a way he can confirm with a single word. Choose a place that's easy to find and low pressure, somewhere busy enough that neither of you feels stuck if it goes badly.

Decide whether you're saying yes before you hit send. A hedge like maybe or let me see tends to read as a soft no unless you follow up within a day. If you want to go, say so plainly and attach the plan. If you don't, decline kindly and only leave the door open if you actually mean it.

Give him a window before you read anything into the silence. Most people answer the same day or the next, so a full day without a response is normal, and two days on a busy week still isn't a verdict. Don't send anything else during that window.

If it passes, one short follow-up is fair. Keep it light, don't repeat the whole plan, and don't ask why he went quiet. Something that makes it easy to answer works better than a message that makes him feel accountable. If he still doesn't respond, let it rest. A third message turns a casual invite into a test you're running on him, and he'll feel it.