Disclaimer: I consider myself to be an ally to the LGTBQ+ community, but I am a cis-gendered woman. I have spent a good deal of time thinking about how to present this topic without unintentionally offending anyone. I am still learning and understanding, so please forgive any transgressions I make. I welcome constructive criticism in an effort to educate, but will not tolerate any hateful comments. Thank you and let’s get right on with the blog.
In the 400+ years since Shakespeare wrote Twelfth Night, we have learned a lot of gender, sexuality, and love. Whatever your beliefs on the subject, it can’t be denied that as a society there is a greater discussion over what it means to love another person, no matter his, her, or their gender. This was not a discussion Shakespeare was having as he wrote the play. His intentions likely had nothing to do with statements on gender. He was simply trying to entertain as he wove these complex love triangles. Regardless of intent, the romantic relationships of Twelfth Night provide for us – the modern audience – an interesting depiction of what it means to fall in love with another person, and that is what we will be examining today.
We’ll start with the love triangle which serves as the primary focus of the play: Orsino, Viola (Cesario), and Olivia. Viola loves Orsino, who “loves” Olivia, who loves Viola (as Cesario). It is a classic case of everyone falling in love with the wrong person. However, if we go a little deeper, the relationships become much more complex.
Orsino loves Olivia?
Let’s start with the relatively simple, straightforward case of man loves woman.
Orsino’s apparent love for Olivia is what sets all the events in motion. When we first meet Orsino, he is pining for Olivia, his unrequited love. On the surface, it was a good match. They are both of noble birth and well respected in the community. A marriage would have been advantageous for both parties. Unfortunately for Orsino, Olivia has no interest in him or apparently any suitor. We’ll quickly see that this is not necessarily true.
Their love would be considered rather superficial today. They rarely interacted as Orsino sent others to woo on his behalf. Since she is in mourning and avoiding all people, they haven’t really spoken all that much. Not to mention, they quickly move on from one another, but more on that later.
Yes, Orsino loving Olivia is the most obvious choice, but it doesn’t work out because they both fall in love with the same “man”
Olivia loves Cesario (Viola)
Olivia falls for Cesario during their very first conversation. At first, she intends to dismiss him like all of the other messengers Orsino has sent. However, this particular messenger is cheekier than all the rest, bordering on down right insulting. Once she is challenged by this young man, she immediately falls in love with him.
The problem is, he isn’t really a man, is he? He is actually Viola dressed as a man. There are clear implications of physical attraction, but it wasn’t like she fell in love immediately upon seeing Cesario’s face. It isn’t until Cesario is snarky and not the typical suitor that she decides he is worth the trouble. In other words, it is his mind that she falls for, not his looks. 
And it’s not as though Viola could disguise her mind. She goes off script, showing her true nature, and that is what Olivia finds attractive. This begs the question: did Olivia really fall in love with a woman?
What does it mean to love another person? Is it the “person” you love, or their physical attributes, or both? These are important considerations when contextualizing Twelfth Night within our modern gender/sexuality discourse. It’s impossible to know whether or not Olivia would have loved Viola as herself, or if it would be a more platonic love. However, we can examine how these characters can serve as reflections of the struggles many today are facing.
For example, a few years back I had lunch with my cousin. She was letting me know that she is currently dating a woman. This was a surprise, but I was thrilled she had found someone she loved. As we talked, she said something that has stuck with me and kept coming to mind as I thought about this post. She said that she wasn’t sure if she was only attracted to women. To her, it was more about the person than the biological sex.
I have thought about this a lot as I consider the relationship between Olivia and Viola. Olivia falls in love with Viola’s mind. Perhaps she falls more quickly because she thinks that Viola is Cesario. It is expected that she will love a man, but she doesn’t want to. That is until she meets the right man. A man whose personality is one she can imagine spending forever with. Problem is, that personality is Viola’s, a woman’s.
Olivia’s love for Viola gives us one look into love outside of man and woman, but let’s get a little more complicated.
Orsino loves Viola (Cesario)
In all of the stage productions I have seen, when Orsino and Cesario sit together listening to music, they almost kiss. This would indicate to me that this is not a particularly groundbreaking staging of the scene. It is meant to help build the love story between Viola and Orsino while giving us a chuckle because it’s so, so awkward.
But let’s consider the situation from Orsino’s point of view. Here is this young eunuch that came out of nowhere and quickly become his closest confidant. They clearly have spent a lot of time talking and getting to know each other. They have become very close. The two “men” have become intimate on every level except physical.
Now let’s return to the crucial scene where they sit and listen to music. This is when their intimacy nearly becomes physical. If you are Orsino, you have briefly considered kissing your closest male friend. That is, until you remember that Cesario is in fact a man. But, for a brief moment, it didn’t matter that he was a man.
Let’s consider the implications of that moment. There is a more overt example of physical attraction being secondary to emotional intimacy. It doesn’t matter until the very last moment that Cesario is a man. Orsino loves this person. He is willing to go to the brink of kissing, but won’t quite go all the way. Why? Because he thinks Cesario is a man, which only matters to him because he believes himself to be a straight man.
What if we set Twelfth Night in 2019, or even 2025, where loving someone of the same gender doesn’t matter. Would Orsino kiss Cesario? Maybe. Orsino’s experience can be a reflection of the questions a young person may have about their own gender.
And then there’s Antonio…
When I first saw Twelfth Night performed, I had never read it and knew very little about the story. Antonio was performed by a woman and was called Antonia. I didn’t think much of it until I saw the clear love that Antonia had for Sebastian. I was taken aback. Was Antonia a woman in the original play? I mean, she clearly loves Sebastian.
Alas, Antonio was a man in the original play, which may leave one wondering why he seems so committed to Sebastian. These deeply committed male friendships were surprisingly less stigmatized in Shakespeare’s time. In fact, marriage was often thought to ruin these important friendships. This is probably what Shakespeare was going for.
However, we’re not in Elizabethan England, we’re in 2019. Let’s bring our own societal hang ups to the play. Antonio definitely has the hots for Sebastian. He’s willing to risk his own life to protect Sebastian.Then, he’s heartbroken when it appears that Sebastian has abandoned him. If that’s not love, I don’t know what is and both these men know that the other is a man. Unfortunately for Antonio, Sebastian is undeniably straight. This is an unrequited love that I’m sure a few homosexual or bisexual men can identify with.
I want to take the time to say that I am not by any means asserting that this is the only or most important reading of the play. The characters only exist within the confines of the text. We do not have Shakespeare providing character development after the fact, so there is a definite need to understand the work in terms of the period it was written. However, what makes Shakespeare so lasting is that people today can relate to the characters. We can find within the text situations and characters that relate directly to the conversations we are having today. That is what I am trying to highlight with this blog. One way we might bring Twelfth Night into the 21st century.
Ripe Good Scholar 
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