Dave is a single, successful, prototypical “nice guy” who embarks on a introspective journey not only to discover what relationship options are available, but also to understand his own worth and what he truly wants. After getting divorced, he tried various websites, high-end matchmaking services, and spent a ridiculous amount of money without much in return. Although he vigorously rejects the “sugar daddy” label as offensive to someone who is fit, attractive, and not desperate, he realizes that arrangement-based structures may work for someone who may not want marriage, but still seeks love.

Best friend of Dave for nearly 20 years and fellow Iowan – but completely opposite in behavior, confidence and philosophy. A guy who walks the talk – brutal, humorous, cynical yet insightful. He understands the human condition and speaks the truth with everyone. Believes in “polyamorism” and maintains full honesty in relationships. He is equally frustrated and amused by Dave and wonders why he keeps making the same mistakes. His sage advice is usually delivered while playing hoops, ping pong or from the driver’s seat. Danny is a professional photographer and creative artist. Check out his website at www.DannyBollinger.com.

Dave and Kristy met years ago when she helped him update his hair and wardrobe. Fellow Scorpio, business owner, and woman of many hairstyles. Kristy’s business objectives are top priority, but she is still in search of true love. She has no problem drawing in men, and she has been on almost every relationship website you can imagine, but the search still continues. While she admits these arrangement relationships make sense for some people, she’s not sure it makes sense for her.  Kristy lives in Chicago, where she owns and operates Studio Within Spa in Lakeview.

George has been Dave’s close friend and colleague for over 20 years. Together they co-founded realFIT in 2012 and their friendship is not only based on their shared Midwestern upbringing, but a true understanding of life in the business world.  George is a former CEO and current CFO with an incredible track record of company turnarounds. In his personal life, George is a divorced single father with full custody of a young son, which is his top priority.  Like Dave, he struggles how to find time for a normal relationship with his other demands.  Given their shared analytical foundation, George provides an authoritative voice of reason for Dave in his journey.

Dr. Lamar is a successful doctor with more that 25 years experience in Dallas, TX. Lamar is someone who helps Dave understand the world of “arrangements” and what it means to everyone involved. Divorced and focused on his career, he is open about his own experiences and why it makes sense for him. Warm, articulate and generous, he shatters the stereotypical “sugar daddy” persona.

Mary was very blessed to have married the love of her life and stayed married for 27 years until his death. Her motto is “first time for love, second time for money.” She believes all women have what all men want, so why not use it to their advantage? Mary represents a well-kept woman beyond the stereotype, with a rational perspective that makes sense. Her experiences help Dave realize that arrangements across all age, income, and geographical boundaries.