Kind of sounds wrong but I am of the appropriate age to be qualifying Students (by that I mean college).

(I've even heard people akin it to pulling teeth

)
A lot of people (specifically girls) who are of my age group do not particularly have much going for them, so the good old, "What do you have going for you?" Doesn't work so well... (some people akin it to pulling teeth)
So I thought of this, and have tried it out a few times on AIM, with someone I knew (yeah I know not the best field test) but I thought I'd share it with you guys and see what the "experts" think.
Me: Why am I IMing you? (= to Why am I talking to you?)
Them: What?
Me: I'm sitting here talking to you, but what do you have to give me?
Them: *giggle, haha*
Me: I mean what do you have going for you?
Them: What?
Me: Can you tell me what's interesting about you, or what you have going for you in your life?
Them: Well I have my boobs...
Me: So all you have going for you is your boobs? (slight neg/ tease)
Them: *giggle*
If they don't get it at this point, or say something stupid, or whatever, you say this...
Me: I am only kidding, but it's an interesting thought isn't it, I think it's the bases of a lot of self confidence issues around people our age, that they don't really know what they have going for them, or who they are or what they are truly interested in.
This is a slight neg, and has the reaction of getting people to really think about their answer, so that you can qualify. It also shows off your deeper side (DHV?) and that you are interested and socially aware(?).
I don't know I am only a noob at this, but this came about kind of accidentally and I wasn't going to post until I had something truly good to post, so I'm just curious what you all have to say about this.