BACKGROUND: There has been a rise in the number of cases diagnosed as lymphogranuloma venereum (LGV), caused by the transmission of Chlamydia trachomatis, specifically serotypes L1, L2, and L3, mostly in men who have sex with men (MSM). LGV can clinically manifest as rectal discomfort, bleeding, and mucoid discharge mimicking inflammatory bowel disease (IBD). Therefore, the role of a wholesome collection of patient history along with gaining patient trust and ease in reporting different elements of their life- whether social or sexual history-could greatly guide physician's investigations leading to timely and more efficient diagnosis. CASE SUMMARY: A 38-year-old male presenting with symptoms of rectal bleeding, mucoid discharge, and abdominal pain during the past month. Initial treatment for hemorrhoids given at an outpatient clinic did not improve the patient's complaints warranting further examinations, whereby endoscopy revealed the presence of mucosal edema and ulcerations in the rectosigmoid area rendering IBD a plausible diagnosis theoretically, but practically refuted due to the negative biopsy results, and positive result of nucleic acid amplification testing of the rectal swab sample for Chlamydia trachomatis. The latter results are in accordance with the diagnosis of LGV proctosigmoiditis. Accordingly, medical therapy with doxycycline was instituted, which yielded a notable symptomatic relief, and an education on safe sexual practices. CONCLUSION: LGV proctosigmoiditis is a crucial differential diagnosis in high risk patients, such as MSM that should be differentiated from IBD. Obtaining a thorough sexual history is pivotal to prevent misdiagnosis and guarantee prompt, effective therapy.