29th and Gay

29th and Gay is a 2005 comedy film from DaisyPictures directed by Carrie Preston and starring James Vasquez, Nicole Marcks, David McBean, Mike Doyle, and Annie Hinton. It was Vasquezs first experience as a writer, actor, and editor.

Throughout his long journey to find a partner, James dates many different guys, many of whom he meets in gay bars. He attempts to find a man online, which leads him to Mike. They go on a date, which seems to be perfect, but Mike never calls back. Throughout his relationship troubles, James also deals with his parents, who try to be much too accepting they buy him overly stereotypical gifts such as musicals and a sex swing for special occasions, a lack of a job, a lack of inspiration for his talents as an actor and his lack of confidence to approach the man to whom he crushes on, the hot and sexy coffee barista in the cafe down the street. After going through friendship troubles, all too depressing moments and losing his apartments electricity, he struggles his way back into life by getting an acting job and perhaps finding the man of his dreams.

Source: Wikipedia