One of the interesting things about Shakespeare’s play All’s Well That Ends Well is the paradoxical plight of Bertram. For all intents and purposes, he just wants to have a little fun as a young man. He is dealt a weird hand of cards, though. When the king personally commands him to marry a woman obsessed with him, we can understand his unhappiness. Anyways, he feels how he feels, and he flees. 

What else could he have done? Staying to marry the woman his mother and the king want him to would put him in the position to become resentful to them all. Running away only bought him some time to catch his breath, and he turned that time into an opportunity to seduce a virgin. The moral ambiguity of this play is so perfectly balanced it is equally easy or difficult to take either Helena’s or Bertram’s side.

Bertram is after all, the subject of a female gaze, a victim of sexually motivated exploitation. Laura Mulvey wrote about the male gaze in the context of art history and that has become a very influential way of analyzing paintings and representations of women. In this play, however, Shakespeare gives us a portrait of a woman who is actively objectifying and fantasizing about a man. She goes beyond representation or fantasy, however, and coordinates sex with the object of her desire. Ironically, Bertram has the energy of a rapist, but he is the one who ends up being sexually violated.

Bertram thinks that he is giving the business to the virgin Diana but he’s really having sex with Helena. The scene immediately following their sexual encounter shows us a disturbing portrait of a woman who has trapped her husband into impregnating her. She rapes Bertram by tricking him into having sex with her, and when it is over, she reflects on how easily he was fooled. She thinks about how hot blooded and crazed he was in the moment and how he didn’t even realize he wasn’t having sex with Diana.

Clearly, there’s something super creepy about Helena. She also spies on people throughout the play, pretending to be someone else. When she gets to Italy, Bertram is already famous for being brave during a battle and when she is hearing the story about him and how he had left France because he was forced into a marriage, she says she knows the woman. 

Helena is an undercover agent, and we see her making her moves with unrelenting will. Helena is more than a stage five clinger; she’s obsessed. She chose Bertram, researched his background, used political leverage to entrap him in marriage, stole his mother’s loyalty and tricked him into sex. If the genders were reversed, this would be the portrait of an absolute psycho. Because she is raping her husband and stopping a man from taking advantage of a virgin, the morality of her actions is ambiguous.

Helena also uses Bertram to climb the social ladder of her times. She is the daughter of a physician. He was a famous doctor but still inferior in social class. Bertram belongs to the ruling class. As a nobleman, he feels entitled to certain rights and he regards most categories of people as socially inferior. Helena’s path of upward mobility uses Bertram like a mule.

Bertram is what Al Bundy would later embody in US American television, the defeated alpha. This play shows what Al would have been like at the peak of his football career before being conquered by Peg. Because Bertram is young and physically attractive, he wants to take advantage of his time, but he is too stupid and ultimately is outwitted by the sex-hungry and power-savvy Helena.

Part of what keeps the scales balanced in this play is the general creepiness of Bertram and his partner in sexual adventuring, Parolles. Parolles has a way with words and talks women into having sex with him. He gives arguments against virginity, saying that being a virgin is an insult to a woman’s mother. Bertram and Parolles would have a podcast and would live in a content house, today. Just a couple of hounds trying to get laid, they are famous for their philandering ways.

There are two different worlds colliding in the play. There’s the happy go get lucky world of the soldier bachelors and there’s the world of family and the court. Bertram and Parolles flee the court to indulge in sexual adventures. Helena, deprived of the ability to flee, uses the political structure of the court to conquer the object of her sexual desire. Ultimately, Helena gets what she wants. She is the hero, or more successful antihero of the play. For her, the ends justify the means. Her dishonesty, her political climbing, her sexual deception, and her obsession with a handsome man somehow balance out in a world full of inequality and fuck bois.