Reuben Feffer

Living... in New York City. Reuben lives in the West 60s, just half a block from Central Park. His apartment is a steal at $85 dollars a month. It's a great apartment that he found through Lisa, his real-estate agent and soon to be ex-wife. Lisa dumped him during the honeymoon because she claimed she got spooked and needed to “explore.”

Profession... Senior Risk Assessment Analyst. Reuben literally gets paid to worry, which is great because he’s a natural. He's been with the same company for three years and 10 months, and now he is facing his toughest case. Leland Van Lew is going to be the CEO of a publicly traded company and needs life insurance. It's a high-profile project because Leland was on the cover of Forbes last year. But he has been called one of the riskiest sons of bitches alive. He's an Australian who is an extreme sports fanatic. It's probably a long shot, but if Reuben can pull this deal together, there might be an extra bonus.

Relationship Status... moving on. He has started to date Polly, a woman he knew back in middle school. After all these years, they ran into each other on the street. Polly has changed a lot since seventh grade, when she was in the Model U.N., the chess club, and a "mathlete." Now, Polly is a free spirit who writes children’s books about kids who get maimed, has a tattoo, and mostly eats spicy ethnic food. She is introducing Reuben to a whole new world.

Challenge... making up his mind. Things were going great with Polly, but then Lisa showed up on his doorstep wanting to get back together. Rueben just wants to make sure he's making the right decision.

Personality... neurotic, but he can't help it. He knows too much. As he says, “I know that I have a .013% chance of being hit by a car on my way home. Or a 1 in 46,000 chance of falling through a subway grate. So I try to manage that risk by avoiding danger and having a plan and knowing what my next move is.” But as he is finding out, he misses out on a lot in life if he is too careful. Sometimes you have to take a risk, no matter what the “numbers” say.