Jul 21, 2009 ... Cindy Wilbur, a 59-year-old married-but-separated executive from Chicago, ... The Internet is rife with married men dating (and cheating). ...One good question to ask "separated" men is if they are in the process of .... So, my experience is dating someone who is separated usually ...My gf has just started dating a separated man, but he seems a little too eager to be in a relationship with her- as in he calls every night ...What concerns me is his marital status, and the reason is that personally, I do not advocate dating separated men to a single women. ...