This one is as short as #2 and is nearly an ideal start, you are just missing one dance, but it ends in a night club, so that’s easy to solve. This is a romantic start that gets you to a fancy restaurant.

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 “Start of a Romantic Evening” 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 a nice jacket
Compliment her looks
Read her a poem
Mark but this flea, and mark in this
Move in closer
Kiss her
Go somewhere else
Turn on some music
Play a romantic playlist
Kiss her while dancing
Go somewhere else
Let’s go out to dinner
Wait in the hallway
Order dinner
Talk to her
Do you like watching movies?
I mostly watch adult films
Give her a compliment
Sorry if I am staring, that dress...
Drink Wine
Pick up the check

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.

A start like this is the only way to get to a romantic walk on the beach, but it could also easily lead to the strip club, boating, or photo shoot at the park.