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Hello I am Dr. Joey. Thanks for trusting me to help you and your pet today. I am a licensed veterinarian with over 16 years of experience. I look forward to working with you.
I am so sorry to hear Jake is experiencing urinary issues again. Our top worries with what you have reported is he may have a simple urinary tract infection or another bladder/urethral stone or there may be something else more structural (scarring, polyp, mass/tumor) that may be going on with the bladder or elsewhere in the urinary system. Being optimistic, let us hope this is a simple urinary tract infection.
You should have him seen today by his veterinarian and get his urine checked. Your vet may recommend do some imaging (radiographs or ultrasound) to ensure no structural issue in the system and no bladder/kidney/urethral stones are present.
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