There is this girl I have been seeing in my school, who I assume is a freshman. Usually I see her in the hall talking to some friends by our main staircase after lunch. I could easily walk over there and say something, but she seems pretty shy. The best opener I thought of to use would be the Drug dealer opener by aceofhearts. In which, I would approach them and ask them if my friend looks like a drug dealer, and explain how someone tapped him on the shoulder and asked if he was holding. (This actually happened to him too XD) Then I thought I could just move into talking about school, and ask their grade etc.

However, my friend is pretty self concious and shy, so I doubt he would let me do this.

Any ideas?

Also, sometimes she is with just one female friend, and other times there's a mixed group of 5-6 guys and girls

What level of school is your friend in? It would determine the opener used.

Generally situational openers work better in high school and middle school.

For college/ grad school use opinion or situational or situational opinion openers.

we're in highschool

If you're friend is shy, just say "Do I look like a drug dealer", they'll say yes or no, maybe. Then just go into the "Well some guy came and tapped me on the shoulder and shook my hand, holding a $20 bill and I had no idea what was going on", I'd recommend then asking what grade she is in, and her name but don't get into too much fluff talk, and if she is in a group be sure not to just focus on her but focus on talking to the group as well.

in this case for example, you should talk first to her friends or her?

When doing the drug dealer skit, say "hey do you guys think I look like a drug dealer (other drug dealer stuff here)" so I mean you aren't singling out anyone. Then just say "I'm (your name) by the way" after they've said their crap, they'll say their names and be on your way with whatever mid-game, negs, DHV stuff, so on and so forth.