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What antibiotics was he taking? There wouldn't necessarily need to be a discharge or pain on urination for a chlamydia infection to be present but if there is pain in general this would almost certainly be made worse during urination. I think he should go and get a full STD screen, chlamydia and gonorrhoea are tested by a swab and a urine sample. Syphillis and HIV are the ones that require a blood sample but there is absolutely no suggestion he has either of these. Some UTIs can be very persistent it just depends on what is causing it and the antibiotic that is prescribed to treat it.