My teenage son, Jacob, is disconnected. He is hunched over his iPod, skull candy in his ears. I tap him on the arm to get his attention.
"Are you okay?" I ask.
"She's not talking to me, mom. Shouldn't she talk to me? I am her boyfriend."
"She is having a hard time right now. You can't make someone talk to you if they aren't ready."
He slouches down in his chair, "This is so hard."

I feel his pain and am reliving my teenage angst through him. Each day in his world is so full of life and the joy and suffering of being fully human.

Recently we went on a vacation to Hawaii. On the bus, he met Katelyn, a girl from Australia. I watched the whole courting go down. She was sitting 3 seats away. Slowly, she made the moves toward him and he sat there letting her move in. It was very sweet and it lightened me up a bit. The next night, she asked him to meet her on the beach. Jacob asked me if it was okay to go. I asked him if his girlfriend, Adriana, back home would be okay with it. He said, "Of course, mom, I'm just going to the beach."
I let him go. I let him go the next night, too.
Then his girlfriend found out. She was not happy. On the last night of our vacation, my son had to call off his rendezvous with the Australian girl.
"I'm never going to see her again, am I, mom?"
"Probably not."
"Adriana is mad at me. Why did you let me go to the beach with Katelyn?"
"Because everyone needs to feel the magic of a holiday romance."
"I didn't even hold her hand, mom. I didn't even hug her."
"I know, but what is the greatest memory for you from our vacation?"
He looked me straight in the eye, "Sitting on the beach and talking to Katelyn."

Now that he is going through this pain with Adriana, I am struggling with my decision of giving him the freedom I gave him on vacation. I am questioning if it is my job to protect him from this pain or if my only job is to tap him on the arm and ask him if everything is alright.

My gut is saying that giving him that freedom and experience was worth it. My gut is saying it's all going to be okay.