Dear Steve and Shirley,

First congratulations Shirley on your engagement. This letter is directed more towards Steve because of his days doing comedy tours. Now I have read both Act Like A Lady Think Like A Man and Straight Talk No Chasers. I am following the rules setting standards and everything is going well, but there is one hiccup. How does the 90 days work when we can only see each other every 60 to 90 days?

The person that I am interested in is a long hall truck driver. We live on the east coast but his job takes him from Texas to California and New York and all the states in between. Now we have had the luxury of meeting each other 24 years ago in high school but we were not friends. Recently we held our class reunion and I made the first move the day after by in boxing him on Facebook. We have become fast friends and we feel very connected.

He is not taking his week off until homecoming when our class is having another get together. This get together put us at 90 days. How can I know that he is worthy of the cookie since our first real date will not happen until 90 days later? Often he says to me that we have to be transparent with one another. We are both approaching this relationship differently. He asked me first about marriage. He wanted to know if I wanted to be married again. He says he wants a wife. I am ready to experience a meaningful relationship that leads to marriage.

Steve, Shirley, Carla, Junior, not Nephew Tommy, maybe Eugene, or Oatmeal please advise me on how to approach this relationship. When will it be acceptable to give him the cookie?

A little back ground information he is restarting his own trucking company and has just ordered two new trucks. I am taking a year off from law school while working on my masters of library science and getting my oldest out of high school. His business is very demanding and law school can be overwhelming too for a much younger student. I am a 38-year-old single mother of two. Do I give or keep my cookie?