How should I handle this situation?

[nlnut]

OK. Ill try and make this as short as possible. Last night I allowed a close friend to play on my stars account. I went too bed. I trust this guy with my life. He told me he was gonna single table 1-2 nl. He sat down at 1/2 nl and lost $200. He then sat down at 3/6 no limit and lost another $200. He sits down at 5/10 nl and loses $600. He is now down $1000. He takes $1000 to 10/20 nl and cashes out for $3500. Total session profit was $1500. Now heres the point....if he had lost the $2000 it would have taken him months to pay me. I'm just shocked and really pissed he did this. I just woke up this morning and found his note that he won $1500...and hes asking....can I stop over later today for the money? How do I handle this? Obviously Ill never let him play alone again.....but in addition to that what should I do?