Pitching is hard, let's do it together!

A great contest hosted by Brenda Drake is coming up in March--Pitch Madness! It's like March Madness, only way better and with less basketball. Just kidding. There's no basketball involved (I hope). To read more about the contest, click here.
To enter the contest, you'll need a 35-word pitch (as well as the first 250 words of your MS, but you already have that!) When I read that part of the guidelines, I was like, "Seriously? I have a query letter, synopsis, and a couple of Twitter-length pitches, and now I need THIS?" It can be hard to come up with so many different ways to "sell" people on your novel, but guess what? We didn't enter the writing game expecting it to be easy. A 35-word pitch (also known as an elevator pitch) is highly useful at writing conferences, so it's good to have on hand!
I'll be working on my pitch here on the blog, and I hope that others who'd like help will stop by, too. If you post your pitch in the comments I will reply and offer my suggestions, and the idea is for other people to help out as well. What I've learned about the online writing community is that it is AWESOME, and everyone is totally supportive of everyone else. I've received tons of help over the past few months, and I'm excited to pay it forward in my own way.
So what do you need for this pitch? How are you supposed to sum up your book in 35 words or less?
We need to know the WHO: Who is your main character, and what makes him or her special?
WHAT is the challenge they face?
WHY is your book different from others? Or in other words, what makes it unique?

If you need help getting started, here are some resources:
Upstart Crow Literary
NA Alley
Nathan Bransford

So, here's my first attempt. Comments welcome!
Anna's strong sense of familial loyalty keeps her home with her lonely widower father after high school. A Shakespeare Festival roadtrip satisfies her need to travel, and brings love and balance to her life.

I think I have the WHO and WHY down, but not enough of the conflict. I'll try to get that across in attempt number two!

Okay, it's been a couple days, here's my next try:
Anna defers her dreams of independence so her widower father won't be lonely. An impromptu Shakespeare Festival roadtrip threatens to tear down her façade of contentment and leaves her aching to live her own life.

What do you think? Does it show more conflict?