If I have a female partner… how likely would she be asymptomatic for 5 months if we had regular sex? She recently had urine testing done and everything was negative, she commonly gets UTIs so she gets tested for gon/clam/trich with the urine tests. 

There's been a lot of medical and social media attention in the last few years about oral chlamydia. Almost all is far, far exaggerated:  this is perhaps the biggest nothing burger in STI problems these days. There is almost no chance you have oral chlamydia or ever did, and therefore little if any possibility you infected your partner.

Chamydia doesn't take well to the oral cavity. Even when exposed, infection rarely takes hold. When oral chlamydia testing is positive, more than half the time it's not living chlamydia, but only its RNA, meaning it is non-infectious. So even when oral chlamydia is present, it almost never is transmitted to a partner's genitals. It's also not transmitted by kissing. Further, oral chlamydia causes no symptoms (unlike oral gonorrhea). And it clears up in a few weeks without treatment.

So the chance your oral sex partner 5 months ago had oral chlamydia is extremely low, and your chance of catching it -- even if she was infected -- was zero or close to it. If despite all that you had been infected, it would be gone by now:  genital (urethral) chlamydia in males is almost always cleared by the immune system long before 5 months. Finally, your partner's negative test is solid evidence you didn't infect her. (Good for her for being STD tested when she gets UTI symptoms! FYI, UTIs in women commonly are triggered by sex. If that seems to be happening, there are easy prevention strategies. Let me know if you and she would like to hear more.)

So no worries about chlamydia. Let me know if anything isn't clear. In the future, simply disregard oral chlamydia. It's simply not a realistic risk, and not important even when someone has it.

HHH, MD

Random thoughts- if a man hasn’t cleared chlamydia would he most likely get symptoms? How about women… would they stay asymptomatic for months on end? 

Trying to wrap my head around chlamydia and how it is asymptomatic most of the time. 

You've somewhat overstated the asymptomatic nature of chlamydia. Usually asymptomatic in the cervix and hence in women, and in the rectum in both women and men who have sex with men. That said, symptoms aren't rare in any of these situations -- up to 50% of even cervical and rectal infections cause symptoms. (But oral infections never do, as far as is known.) Urethral infection in men has obvious symptoms probably in 80-90% of infections. Therefore, absence of urethral discharge and painful urination in males is good but not conclusive evidence against urethral infection. Symptoms probably decrease over time, however. OTOH, within a few months it goes away entirely -- not just symptoms, the infection itself is eradicated by the immune system.

You can limit the "wrong data" problem -- and medical internet misinformation in general -- if you limit online searching to professionally run or moderated sites (like this one); and especially avoid those run by and for people with particular problems (like Reddit).

Best wishes and stay safe!