I'm curious if this occurs more often than not? I am aware some gentlemen repeat with the same lady on a regular basis and I'm curious if the lines of business vs friendship vs more than friends ever cross? Do you start to believe that there is more to the relationship as opposed to strictly a business relationship? Do lunch dates possibly dinner dates get thrown into the mix along with taking vacations together? How about taking a lady for hire to an event, perhaps a Christmas party etc...... At one of my company's events it was noted one of the VP's had quite an attractive younger woman on his arm. Needless to say eyebrows were raised and some were suspicious of the relationship. An older very well to do man with a much younger attractive woman always leads to speculation.