So I've gotten the nude pictures of Jenna and have linked them in chat. I ask her if she wants to meet and she goes into what seems to be a dialog loop of "I dont care" and "whatever". What do I do to advance the story?

If you send her the nude pictures as an attachment, she should say something like you are a bastard.

Say something like 'I want to see you naked'.

So keep on talking to her, she has not left the chat, so that is a good sign.

Then after a while she can be persuaded to meet you, if you delete the photos.

If you want to start the chat again, select the last point in the stories menu and click on apply.

Okay, that worked, Thanks for the help.