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Alternatively, you can just increase realtions with an enamoured lady and sneak in to visit her with or without her father's permission.
It is not possible to be wooing "too many" ladies. You can enter into romances with every female in the game, if you like.
There used to be a Special Trait available (or maybe still is?), where the player can get a charisma/persuasion? bonus for dating numerous ladies at one time. When I was trying to test that out, I dated dozens of women and got them all to 100 relations...the only limitation is how well you can manage your own time. [My best guess at this point, is that you need permission from ten or more different lords to date their daughters and get them all to 100 relations? Or maybe it simply is an option that has been patched out?]
The problem I'm seeing from what is written above is that the human player seems to think that his character is so amazing that all women should swoon everytime he walks by. That player is wrong. First, you must impress the lady so that she wants the character to come for a visit. Then gaining the trust and respect of her lord will make it all that much easier.
It's not up to the character to decide when and where to meet his lady love. You get to wait until you are summoned, then its perfectly simple. With multiple ladies, these reports come in a regular pattern and you can plan your movements accordingly.
In most cases, you get the chance to meet a lady at a feast. After a tournament, you can dedicate your victory to the lady, which may or may not impress her enough to get the romance options started. Then you wait for an invitation to go and read her some poetry.
If you accept a quest from a lady you don't know, at a feast, you might well wind up carrying that amber or whatever around with you for a very long time. Unwed ladies cannot be accessed without permission even if you go to the castle you know she is in. Talking to her mother or her sisters, etc. has nothing to do with it. They will never spawn on any map and will only appear at feasts (assuming there is room for her to spawn in the hall).
Perhaps, like the feasts, there is a limitation for how many ladies can spawn at a castle or something? I would suspect that the ones you have the highest relations (and permissions) with should be moved to the top of the list. I also cannot think of any families where a lady might have seven sisters?
Without more relevant details, it's kind of difficult to offer possible solutions to such a strange problem. All I can do is point out what works in vanilla and hope that you find something useful in there.
Good luck with that.