A personal finance program with a sample file to try
Money by Zaweba has File > Try the sample file, which makes a fresh example household so you can explore before entering your own figures.

Yes, and it is free: Money by Zaweba has File, then Try the sample file, which makes a fresh example household money file in Documents\Money by Zaweba. You can click through its accounts, transactions, budgets and reports, change things and try features out, all before you type a single real figure.
Starting a finance program with an empty screen is daunting. You can't tell what the reports will look like, whether the budgets make sense to you, or what a month of imports involves, until you've put in a month of data. A sample file shortcuts all of that.
What's inside the sample
The sample is an example household with the sorts of accounts people actually have, filled with transactions so the registers, running balances and reports have something to show. One detail is worth noticing: the house is held as a manually valued investment account. That means the net worth figure isn't just a large mortgage, and you can see how Money treats a property you value by hand with Update value.
Because it's made fresh each time, you can't spoil it. Experiment as much as you like; if it gets messy, make another.
Things to try
Start on the Home page, which Ctrl+H brings back from anywhere. It shows a greeting, account balances, net worth, bills due, this month's budget, a net worth trend and where this month's money went. That gives you a feel for the app at a glance.
Then open an account from the Accounts page on the left and look at the register: date, payee, amount, category, memo, a cleared or reconciled flag and the running balance. Try adding a transaction with Ctrl+T, typing the date as today or as something short like 12/8, and pressing Enter to save it.
Recategorise a payment and watch Money ask whether to always do this for that payee. Open the split dialog on a shop and divide it between two categories. Make a transfer to a savings account by choosing the Transfer entry in the category list, then look in the savings account to see the other half appear.
On the Reports page (Ctrl+R), compare spending by category as a pie and as a bar chart, look at income against spending month by month, and see the net worth line. Try exporting one to PDF to see how the A4 pages come out. Under the Plan menu, look at the budgets and at Bills and deposits.
Moving on to your own figures
When you've seen enough, close the sample and press Ctrl+N for a new money file of your own. There's no need to clear the sample's figures out of anything, because your file starts empty. Keeping the two separate also means you can go back to the sample any time you want to try something without touching your real accounts.
Add your accounts from New account on the File menu, with opening balances and dates, then download a recent statement from your bank's website and import it with Ctrl+I. The CSV wizard and the review screen will look familiar after the sample, and the payee rules will start learning from your first corrections.
Why it helps
A sample file is a small thing, but it answers the questions that usually stop people starting: what will this look like, and will I actually use it. Money by Zaweba is free software under the EULA with no account, so trying it costs nothing but a few minutes, and the sample makes those minutes count.