Can i sue someone twice for the same thing?

If you won your suit in court, then the court should have entered a judgment against your old friend. If you do not have a copy of the judgment, I suggest that you obtain a copy from the courthouse. You should consult with an attorney to examine your options about collecting on the judgment. You should be aware that in Oregon a money judgment will expire after 10 years if you do not renew it. If a judgment was entered in the first case, there should be no reason to file a new lawsuit. Nevetheless, you should consult an attorney.