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If you're going to follow this route, let's fix it. Don't small talk...flirt. Flirting establishes attraction and creates the one connection that you actually need so that she wants to get to know you better, while small talk tends to be rather boring. Boring doesn't build attraction. Don't ask if she's single because if she's on the fence about going out with you, she'll more than likely use that as an excuse to not go out.
You initiate a normal human interaction with flirting in a parcel pick up scenario? If she's remotely conservative, and *authentic* Asian girls are (plus med student?!), she might get scared off. Hell, most girls will be, unless he's a really good looking guy and they are instantly attracted. Small talk isn't boring. Small talk is what normal people do when they don't know anything about one another. Once there's a basic level of comfort established (knowing a little bit about one another) you can get flirty. He needs to open up and connect to her to show her who he really is as quickly as possible. This will polarize her one way or another. Flirting doesn't generate attraction. It begins sexual escalation. That's like jumping to step 3 instead of doing step 1) generating attraction and 2) building comfort and trust. Flirting is going to take WAY more effort and confidence to pull off effectively. Not to mention, how is he going to flirt? Just saying "flirt" is way too vague. I don't see him pulling that off in that situation. And yes, use the "are you single" line - the "on the fence" women need to be written off. Not indecisive bullshit. Too many other women around to be worth the time.
Small talk is boring when it comes to building attraction. Flirting is a normal thing that men and women do. There are timid guys that are afraid to flirt and the
hope that the girl will be interested in their efforts in small talk. Comfort and trust is an overated when it comes to pickup.
I get it. You don't have the confidence and don't have the ability to put in the effort for flirting. Hell, you don't know what flirting is...so you dismiss it as being possible. BTW...you can use the forum search features to clear up the vagueries that you don't understand when it comes to flirting.