1.: You are now working as an escort at the casino, your job is to make as much money for the establishment as you can either by selling yourself or by making them spend money here.
You can come to work in either an elegant outfit or one of the exquisite ones you are given by Leah when you accept her offer.
2.: The more money you make the more you get to keep for yourself. You do not need to accept any assignment but refusing them makes you miss out on money making opportunities and you actually have to pay to avoid getting evaluated by Leah.
3.: Every few days a special client will ask for your company for the whole night. Their identity will depend on your preferences, checked at the time this happens first. Characters preferring male company will get Gregor, characters preferring females get Eleanor.
There are five different dates (not counting the first and the last unique ones) you can go with your special client. Each of them offers an option to basically just do your job and another to try to go the extra mile to give them what they really want.
4.: You need to succeed in all five challenges to trigger the ending for the storyline. If you fail once you can retry the activity but it will increase the waiting period until your client looks for your company again.
4a: Dinner date. Need 3 Charm to succeed.
4b: Party. Triggers after you succeeded at Dinner date. Need 5 Charm to succeed.
4c: Tennis vs. client. Need 2 Fitness to succeed.
4d: Tennis vs. other couple. Triggers after Tennis vs. client. Needs 4 Fitness to succeed.
4e: Art exhibition. Needs 8 Intelligence to succeed.
5: Once you succeed at all five of these you unlock the last date with your client. Accepting his/her proposal gets you the ‘Trophy wife/husband’ ending.