A buddy of mine has a great blog and recently asked for a tip for working with people, specifically students. Whether you deal with teenagers or not, here's what I shared. I hope it's a blessing.
Fully commit yourself to the awkward conversation.
Often when we approach students, they put up a wall of disinterest at our attempt to build a relationship with them. Whether it's legitimate on their end or if they are simply testing you, fully commit yourself the awkward conversation. It's better to have several conversations that go nowhere than it is to never even try because it feels "too hard" to find a way into their life. Ministry is hard - don't pretend it won't be. So make several, several attempts, never giving up. Eventually you'll find something to talk with them about and follow up with.
And if you need an example, you need only look to the constant invitational nature of God. How many times has He tried to build a relationship with us... only to have us brush Him off?