I've spent around 3-4 hours trying to figure out how to date Jenna. I've tried every line I could think of and nothing works. I've gotten as far as her saying "Sure" to a photo shoot, but "No" to meeting. I declare this conversational portion of the game to be unpolished and I am hoping someone out there has a list of exact commands to type to finish this part of the story (don't make me guess).

Please check out these threads.

For getting to meet Jenna:
viewtopic.php?f=7&t=156

And for chatting with jenna later on:
viewtopic.php?f=7&t=97

I've done all of that (in the first link). None of it helped me get her to say she wanted to meet.

You will have to keep repeating some action repeatedly. Like the magazine you work for, ask her about photoshoot. Depening on her answers you might have to repeat each line several times, Till you reach the point where she tells yo to meet her at public bool she gives you a date and time she will be there. If lines do not work it means you messed up and it would be best to restart the story.

Spent a couple hours typing the same commands over and over, and she still only gets to the point where she says "Sure" to wanting to do a photo shoot, but she never says anything about a meeting place. I'm pretty sure there has to be a specific order of repeated lines, and finding this order is impossible.

I find it easiest to keep my answers as short as possible, just answering yes on everything that wont need a specific answer is the simplest way.