Jack is finding his life difficult as he begrudgingly turns 30 years old. He is not professionally or personally established to the extent of which he believes he should be for his age. To cope with the impending birthday, he is determined to ease his anxieties by gifting himself with the best gift he can possibly give himself, which is gifting himself with an irresistible man off the streets. His greatest pleasure is cruising men, getting to know them, and then having a great time with them. However, as he cruises a man who he finds irresistible on the eve of his 30th birthday, he encounters troubles like he never had imagined he would. Adding to his troubles, he also finds himself obsessively attracted to a man who only wants friendship. In time, Jack becomes entangled with a man who grossly disrespects him for his lifestyle. Then, however, he finds hope where he never thought he would find more than the street pleasures he desires. While reading "It Pays to Look Good," one travels the streets of Chicago with Jack and a cast of other believable characters who are engaged in realistic events. "It Pays to Look Good" is a gay urban adventure with romance