Engaging a lawyer to send your friend a letter of demand (LOD) will not be wise in this case as the legal fees and incidentals involved in sending the LOD will be around half of the debt already (NB. it also depends on which law firm you go to). The Small Claims Tribunal is not applicable as it deals only with complaints arising from contracts for goods and services, not personal claims. Do you have a written IOU? SMSes evidencing the debt due to you? If so, you may wish to make a police report. But I am not sure that your friend will be found to have committed a crime. Much as I hate to say this, you may have to consider this an expensive lesson costing S$1,050.00, and write off the debt (and the friendship).