This is a less than ideal start, but it is a fun start to the date: The Park, The Diner, and The Museum

This path is available in the help section of the game. On the main menu click “Help” then click “Paths” on the top row, and next to where it says “Pants Off At The Park” click “Enable”, then start a new game. Correct choices will be highlighted in Magenta. Note: Where there is more than one choice, you might have to do one, then the other when you get to the choice page again. This will give the correct order:

Bring swim suit
Give her a hug
Read her a poem
Mark but this flea, and mark in this
Go to another room
Let’s go for a walk
Take the other swing
Climb on top and hang upside down
Let’s go out to dinner
Hand the waitress a $20.
Eat Dinner
Give her a compliment
You are beautiful, ever consider posing nude?
Talk to her
Renoir
Durer
Rembrandt
Poland
Gustav Klimt
That's not an earring or Is that not a pearl?

The rest of these paths will start where one of these 5 dinner paths end. It is highly recommended to save your game at this point.

And you are now downtown, where you can shop or drink, or go dancing.