Only if you are uncomfortable and make it that way.
Look, this is what I went through. You ask a girl out, she says no. You go home bummed but you feel good about yourself because you had the balls to ask a cute girl out. This is better than going home and wondering what she might have said if you didn't have the balls. This gives you confidence to ask the next one out. Eventually, you ask a cute girl out and she says yes.
Seriously, don't play games. A girl won't go out with you unless you ask them. If they say no, shrug your shoulders, say "No problem, couldn't hurt to ask!" and go on with your day. They won't feel awkward if you don't.
I had a 20-second encounter with a beautiful woman in a store, than she left. I said "f*** it", chased after her and asked for her number. Now she's my wife.