Your analogy confirms my point, because the things that make job interviews so awful are not things people do on dates - not without being crushingly inappropriate. What you're talking about, it seems to me, is contactful conversation. That's precisely what job interviews are not, and that's the problem.
In fact, the dating analogy points toward a saner way for small organizations (as most software teams ought to be) to find people. Get to know one another in a relaxed way. See if there are common interests and values. Do things together. Eat and drink. This is how humans behave.
There are other analogies to look at too - auditions might be one.
The problem is that it's much more costly to make a bad pre-hire, if that's what you want to call it, than it is to go on a bad date.
You can't just bring someone in and let them be their self in the office. You have to have someone onboarding their HR stuff, someone onboarding them on to the technical stuff, someone getting them a laptop and access to source control, someone answering their questions, someone tasking them with things. All this takes time away from people who could be making the company money.
You can start reducing these things (don't give them access to source control, give everyone the same initial tasks) but now you're just reducing it back to a job interview.
What's the biggest problem for software companies right now? Attracting good programmers. That's true of startups, anyway, and as startups go so goes the industry. What that tells me is that those who get ahead of the curve and figure out how to grow teams better are going to have an edge. This is a big deal, and job interviews suck so badly that there is room for innovation.
This is why job interviews are Hard. They involve making judgements about people on fragmentary evidence. You get better at it with experience, but it's never easy and hard to train.
Actually, these days I find hiring managers harder, since it's much more about gut feel than objective criteria.
But saying they're broken is like saying dating is broken. There isn't much of an alternative.
That was what happened when I was interviewed for this job 10 years ago. Unfortunately, we don't do it anymore.
The interviews consisted of HR talk, technical meetings with more people than I can remember, lunch at a local restaurant where we talked about the industry and a few tech topics, and more tech. interviews in the afternoon.
By the end of that very long day, they knew me well enough and I knew them well enough. Sometimes I wish we were still small enough that we had the time/inclination to hold that kind of interview.
In fact, the dating analogy points toward a saner way for small organizations (as most software teams ought to be) to find people. Get to know one another in a relaxed way. See if there are common interests and values. Do things together. Eat and drink. This is how humans behave.
There are other analogies to look at too - auditions might be one.