Courting ladies at same location only allows for you to visit one of the ladies.

[Chris Sterling]

Had three instances of this in my game. I attempted to court Jeyne Westerling at the Crag. She seemed interested (relations jumped from 0 to 16). Got permission from her father to visit her, went back to the castle where the option to "attempt to visit a lady" was present but the only option I had was her younger sister, who wasn't at all interested in me (relations dropped from 0 to -2). The same happened with the Yronwood sisters. I also noticed this with lords I recruited into my own house after completing the Qarthagar quest. My lords without fiefs were offering up their daughters to me, (I think there were 4 at my castle) but it would only allow me to visit with one of them. The problem is once you court a lady the only way to access them again seems to be through the "attempt to visit a lady" option so effectively they are inaccessible. Not really an issue as there are lots of options, but was quite frustrating at first.

[Jared]

I've had this issue too. With Sansa and Arya Stark. Hopefully it gets fixed soon.

[Mal]

same issue with the sand ladies in the south