By forcing a few hands.

As much as I want to say that I can make everything work out with a few messages, I think I may need to play a little dirty to make John happy. He doesn't associate with a lot of people in person and he hides his money very well. Who'd agree to go out with a guy like that? The only thing I can do is make sure they do. Let's see who I can...convince to date John.

Natalie Warner. What an interesting woman. 30 years old and up to her ears in white collar felonies. Few people have stolen as much money from investors as this attractive brunette. Then again, even fewer have done so successfully (until now that is). With a few 'recommendations' on how to buy my silence, I could get her to do anything for John. I could even protect John simply by 'accidentally' turning her in once I feel its time for us to cut ties.

Or how about Maria St. James. A common 21 year old redhead who goes to a religious school, her life would be destroyed if it were announced that she was the vandal who destroyed her schools church. No education, an incredible amount of debt, and the disappointment of her family would definitely be enough of a motivation to get her to perform however I want.

Then again, John may want someone a little less...criminal. Joan Erickson would be best for that. A petite blonde 19 year old who hasn't quite found her place in the world yet, Joan's strict parents would throw her out immediately if they found out what she did for a living: cam modelling. Nothing quite says "I agree to anything" like the threat of being kicked out of a cushy house. On the other hand, getting her thrown on the streets may endear her to dear John if I can get their paths to cross.