Catherine is the first romanceable character you’ll meet in the game.

She will respond better to a Nice Guy approach, although she has a rebellious streak which can be teased out with the Bad Boy persona.
At the start of the game, you’ll want to pursue a Nice Guy persona in order to raise your affinity.

Friday

Before talking to Catherine, you get a Look Closer option. She does notice if you look but providing you’re a nice guy she doesn’t seem to mind.

Offering to help earns 1 Affinity point and 2 Nice guy points. In Easy and Normal game modes, this puts you in a Nice Guy persona with her.

When she hugs you there is an opportunity to grab her butt. You must be a Nice Guy in order to do it, and earn 2 Affinity points in the process. If you’re not a Nice Guy (i.e. didn’t offer to help, or are playing on Hard mode), you will lose Affinity points if you do it.

When presented with the choice of which box to take, you should select ‘Say she looks very sweaty’. She’ll tell you it’s hard work moving all the boxes and she’ll jump in the shower later.
That unlocks the option to spy on her in the evening after she’s taken a shower.
You’ll get the option again of which box to take.

The largest box is called the ‘Panty path’ as when you ask what’s in the box, that’s the first thing she pulls out.

If you ask Catherine, she’ll say to take the smaller box as it’s heavier. This is called the ‘Music path’ as when you ask what’s in the box, she pulls out a music CD.

There is no correct or wrong path. The panty path is more playful, while the music path reveals useful details.

After taking either box, you should offer to help take her heels off.

If you caress her leg she’ll say her shoes don’t go up that far. You’ll get a chance to compliment her ‘Lovely legs’ for an Affinity point.

This is followed by a look closer option up her skirt. Providing you admit to looking ‘Everything looks fine from here.’ She’ll joke that you should be looking at her feet and you’ll gain an Affinity point.

On the Panty path you will tell Catherine you’ve never seen them before, to which she replies you shouldn’t have been looking.
Two options award an Affinity point, but responding that she used to walk around in just a long t-shirt will unlock a little bit extra in the evening’s spy scene.

How you respond to her telling you the panties haven’t been washed will have no immediate effect, but will be remembered for the future.
Neither choice is wrong, but responding ‘Nice’ will have a benefit if you’re interested in Catherine’s future bad boy path

On the Music path, the box will be heavier than expected. Choosing to put the box down will result in planting your head between Catherine’s breasts. If you have high affinity you don’t need to apologize, but if you do she’ll respond that when the two of you used to play fight, your head would often end up between her breasts and that she’s used to it now.
This will open up a little inside joke between the two of you when similar situations occur in the future.

She’ll put out a CD of her singing. You keep the CD as a collectible. You also learn she wants to be a singer.

On this path, she’ll also reveal she has a job as a substitute teacher at Rockbrough College teaching history and art.
You’ll receive Affinity points for taking History (Humanities) and Art (Creative) after learning she’s the teacher.

Catherine’s next scene is spying on her from your window in the evening. If you unlocked the additional part of the scene, she will put a long t-shirt on without any underwear. Otherwise, she will walk out of view and re-emerge wearing the t-shirt.

Sunday

On Sunday evening, just before leaving the Shopping Mall, you have an opportunity to buy flowers for Catherine. These can either be a welcome home gift or good luck on her new job.

When you give the flowers to Catherine, she will lead you into the kitchen to look for a vase. Reaching into a high cupboard will pull her nightshirt up, partially revealing her backside. You can look closer, or try moving in for a better view.
Looking closer is the better option as she will turn around before you get a better view. If you do try moving closer you’ll startle her as she wasn’t expecting you to be so close.

Once the flowers are in a vase, she will ask if you want to watch the movie with her.

There are no additional points awarded for staying to watch the movie. The movie has several sex scenes, since Catherine has drunk a bit of wine she will be tipsy and will rub the popcorn bowl against her crotch. This will lower her inhibitions around you.

Catherine’s next scene will be Monday evening.