First, never ever never ever never tell any civvie woman that you have seen prostitutes. Don't. Not for any reason. I know a lot of women, and lots of prostitutes, and not even sex workers think, deep inside, that guys who hire prostitutes are super desirable. People here will argue, because we don't like to admit we all share a turn-off bad habit like picking our nose and eating it or farting wet ones in bed, but we do. It's not a bragging point. So even though this hobby is a big part of your life and might seem relevant, do not ever tell a girl what you've done.
Second, remember that civvie dating and hiring prostitutes are totally different. Civvie dating is not free prostitution, and the best GFE is never civvie dating. Guys here get this confused all the time, because we're all sort of wrapped up in the hobby and somewhat delusional. But don't be deluded. Hiring prostitutes has certain benefits (and problems); civvie relationships have an entirely different set of benefits (and problems). They are not the same. Do not expect civvie dating to be like your experiences with prostitutes. You cannot buy a civvie girl dinner and chat about your job and family and then suddenly grab her tit and expect her to moan and grab your crotch and suck your dick. It doesn't work that way. The premise of the encounter is totally different.
When you hire a sex worker, you both know exactly why you're there. When you date a civvie, you are exploring, together, a vast set of possible relationships. You might hate each other, you might become nonsexual pals, you might become best friends, you might become fuck buddies. Who knows? Nobody. THis is your source of stress, I think. And it's reasonable. If only we could read her fucking mind and see what she's thinking, what she wants! But we can't. And remember that she can't read your mind either. Thus... Communication is key. Gentle testing is key. If you find her attractive, say so. Be specific. But polite. In general, things she has control over are best, because she will take pride in her work. If she dresses great, say so. If she has a great figure and you know she works at it, say so. If her hair is done really nicely, say so. EVERYONE compliments the eyes. But so what? You're basically complimenting her parents on breeding well and maybe her for not poking them out with a fork as a kid. It's better to praise HER. Find out what she's worked hard on, what she's proud of, and if you admire it (and ONLY if you honestly admire it), then say so. And say why. This rule works, even if it gets you into counterintuitive situations. I have known girls with boob jobs that are tremendously proud of them. They love hearing that they have nice tits, which of course is otherwise something that would normally get you punched in the face for saying.
Along those lines, if you would like to sit closer to her, or hold her hand, do so. Here it gets a little tricky, because women do indeed like bold men. So you don't want to be asking like a sad little puppy every time you want to touch her. Just do it. But maybe prep the ground a bit before hand, or do it in an unselfish way. "I love the way your hair falls along your face like that" (and gently brush her hair aside.) "Are you cold?" (And snuggle closer or grab her hand.) Look at her. I mean really look at her. Talk to her. I mean really talk to her. Eventually, when the moment is right, you will know what to do.
...but yea, the advice about the booze is OK too, if you really need it.
Third, why are you asking this question here? You should be reading the Heartiste.