Oh, hmm, I didn't get that option for some reason and I did as much as I could for Jack. Maybe being in the gang disqualified me or I had the wrong amount of good/evil points.
Yup joining the gang disqualifies most options.
For Jack 3 points are key.
1. Get the piercing when Jessica tells you. No need to get any further piercings or tatoos if you want though Jack appriciates it.
2. At the beach take no one and let Jack put sunscreen on you. if you have the black bikini even better.
3. After you see the paparazzi photos Jack will call you and you need to choose do not mind option. dont choose the love it or angry option. he should ask you out for a date then.
Now you are locked on his romance route and if in a relationship with anyone else you get a chance to reject them and be with Jack. if no relationship he asks you to be his girlfriend. then just have his back all the way.
For Jack the point system only indicates the type of relationship - sweet romance or lustful attraction. played both paths. was pretty good.