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.
If situation would be reverse (girls chasing guys), ladies would be constantly complaining how hard is it to succeed, how afraid are they of the failure/rejection.
It takes time to build the confidence women love so much (unless you are an arrogant extrovert, then you have more than plenty). One of the reasons there are many couples where guy is much older. Not so much the other way around.
That's just a bad mindset. Life is never easy for most people but being a normal guy is more than enough to be successful with women.
Look in the mirror, and see if you'd like to date the person in front of you.
If not, then: Go to the gym, eat and sleep well, stay in shape, fix that bad posture, fix those crooked teeth, groom that neckbeard, wear sharp clothes, get a sharp haircut, go out and practice your social skills and most importantly be confident about yourself.
All of the above can be done by any normal guy as long as you're determined and willing to stick to a long term self improvement plan and put in the necessary work.
The problem is most guys are lazy(I was one of them) and don't want to put in the work to improve themselves and expect women to magic themselves in their arms while they sit on their couch and watch *hub and complain that good looking guys have it easy.
so clearly there's something to be said about how the way you use these apps changes your experience. use the right apps and go for people that seem interesting rather than the most traditionally attractive ones. don't bother trying to make a witty one-liner to get their number immediately, have patience and be fine with having some chats that go nowhere.
No it won't? I know girls who would think of such propositions as friendship related unless you were more direct, but being more direct comes at a risk of appearing "creepy". It's a catch-22.
Not with that attitude. Women respond positively to confident men. How you say it matters more than what you say.
You're absolutely right that it feels off though, to some extent it's dehumanizing. Then again, think about how often you subconciously dismiss people based on looks or first impressions in real life. However, unless you use the app purely to have one night stands you also get the chance to meet great people - many of the nicest people I've met in life have been through apps.