The First Invitation Is Meant To Be Awkward

There is no version of asking a near stranger to do something that does not feel exposing, and waiting for that feeling to pass is a wasted wait.

The first invitation is the hard one. You know somebody slightly, you like them, and to progress it you have to say something that reveals you would like to see them again. There is no phrasing that removes this. Casual phrasing does not remove it, humour does not remove it, and framing it as an accident (you happen to have a spare ticket, you happen to be going anyway) only disguises it, which most people can see through anyway. The exposure is the mechanism, not a flaw in your technique.

What helps is lowering the stakes rather than the sincerity. A specific, small, easily declined proposal is far easier for both sides than a vague warm gesture. We should get a coffee sometime puts the work on the other person and almost always dies. Are you free for a coffee on Thursday morning is answerable, and if the answer is no, the no is about Thursday. Attach it to something already happening, and the whole thing costs less: you are going to the market anyway, you walk that way anyway, the class finishes at the same time anyway.

Then there is the matter of what to do about the ones that do not land. Some will not. The other person is busy, or shy, or content with the friends they have. The temptation is to read this as a verdict on you and stop asking anybody anything, which is by a wide margin the worst available outcome. The realistic expectation is that a decent proportion of invitations go nowhere, that this is the normal rate rather than a bad rate, and that the only way to be wrong about it is to send so few that a single no can carry the whole result.