I mean, I'm shy and awkward as fuck, but when it came down to it that shit was basically a girl asking me, "Hey, do you wanna go to [place] tonight?" or me asking a girl, "Hey, d'you wanna watch some movies tonight (while cuddling and &c.)?"
All of the crippling uncertainty &c. only persists if you allow it to. The key thing to remember is that everyone is that awkward and uncertain at some point, even if they don't show it. Most stay that awkward for a good long while, and the ones that superficially don't are just really good at faking it. If you get to the point where everyone in your age group is either married or genuinely comfortable dating, congratulations, you get to date when people are adults and mostly beyond all the window-dressing bullshit that teens and 20-somethings tack on to "Hello fellow unattached person, how'd you like to share a flexible degree of personal affection?" As long as you're not so inexperienced and incompetent that you'll disappoint your counterpart romantically, behaviorally, or sexually (as the case may be) it's almost entirely superior, barring (so I'm told) the relative lack of energy.
Nonverbal cues can be a pain and a half to sort out if they don't come naturally (even more so now that misinterpreting can lead to a empowered SJWomyn claiming that you (verbally) raped her instead of an awkward moment or embarrassing rejection), but people tend to grow out of the coy/macho bullshit for the most part. The ones that don't aren't worth the time.