Ummm, you just ask. Not as in "Hey, are you single?" but "You seem interesting, how about a coffee next week?". The answer will tell you everything to know.
Seriously guys, women aren't some strange alien creatures, they're human beings and they appreciate it when you're direct and take initiative and hate men who beat it around the bush waiting for the girl to make the first move.
>I'm not attractive enough[...] so dating apps at least get you over that hump
In my experience it's the opposite, you use live dating if you're not attractive enough for dating apps as those favor only the top percentile of attractive men and being average gets you nowhere.