The point is you want to check if you are comfortable where she is, and the other way around. And if this leaves you with a bunch of Nos before the first date, and that's great too. Did you really want dates that weren't going anywhere anyway?
The dating game is not brutal. If you'd put in as much work as you did in engineering, you'd be able to meet women with a half a wink of your eye.
Now I would like to try again. But I am so rusty and awkward with my flirting and dating skills. And I'm pretty sure being honest with a woman about my situation is a bad idea.
How can a man know he is putting his time into the right woman, the woman who will not leave him? You can't. She might get hit by a bus tomorrow, or die of cancer in three years, or just walk out because she is bored of you. Life is uncertain. But…
If he asks them out, and things don't go so well, then he just might lose a friend. The truth is that could happen. But you know what else is true.