Stephen is the main character in the play. The play revolves around his bad luck in getting women and falling for either engaged or disinterested ladies.

Stephen is a person who makes the wrong decisions. After breaking up with Liz, he does not take time to heal from the heartbreak and decides to immediately jump into any relationship in which he believes it can fill the void left by Liz. He does not assess and take time to understand himself or even try to figure out the reason why women are not falling for him and result in organising several dates which do not materialise to a relationship.

Stephen depicts an unwise person. After being heartbroken by Liz, Stephen immediately looks for a rebound from several women, Christine being among them. Aware of Christine’s relationship with William, he cannot thoroughly think through the impact it would have on William if he discovers that his best friend is having a relationship with his fiancée. Stephen also tries to commit suicide after being rejected by Christine and after failing to secure an immediate rebound.

Stephen’s character comes unsuccessful dates and rejection by women. Stephen also draws inspiration from his favourite book Sorrows of Young Werther, and he mainly uses favourite parts of the book to lure his potential dates. Acknowledging that he is dreadful in dating women, Stephen uses the same dating techniques to win the hearts of both the taxi driver and Christine. Stephen believes that girls adore reading books and tries to make them read his favourite book to make them have a common stand about some ideas from the literature material.

Stephen portrays a person who might sabotage another person’s relationship. In the opera, he tries to have a chat with the lady, Mrs X, not acknowledging that she could be in a relationship with the man who was accompanying her. Stephen almost sabotaged his relationship with William after William discovers Stephen is hitting on Christine in the Art Museum. As he believed that he was successfully winning the heart of Christine, Stephen was persuading her to leave William for him and even promised to marry her as soon as they were together.

The play references Stephen as a delusional character who believes that reading romantic books would make him an auspicious date.  He thinks that he is reliving the characters in his favourite books to a point where Stephen gave Christine a cabbage when he discovered they were in love with each other. Stephen believes that everything around his world comes from the literature books and also thinks that his dates ought to live a similar lifestyle as his.

There could be a symbolic meaning in Stephens second name, Hurt. In the play, while making reservations for Mrs X, the receptionist asked if his name meant a person who is experiencing pain. Symbolically, Stephen is experiencing some emotional imbalance and torment as he believes he is unable to secure a perfect date after breaking up with Liz. Stephen displays emotional hurt when Christine decides to marry William. He nearly commits suicide at the end of the play as a result of the emotional pain of being dumped for the second time in a short time frame.

Stephen is a character who is static. He does not exhibit emotional growth and uses the same techniques as luring ladies. He also does not take time to stay away from dating as he fears to be alone forever in his life. The author illustrates Stephen as a meek person who is vulnerable to emotional hurt. This is evident from how other women view Stephen as a soft person and whom they would feel bad if something dreadful would happen to Stephen.