Anyone who attempts to put a label on any aspect of William Shakespeare’s being is treading on quicksand. His mind was able to empathize with and project any personality (male or female, natural or supernatural, king or gravedigger) and to illuminate any situation of life: business, family, politics, romance and warfare. His life and his works demonstrate that he transcended sexuality without any firm boundaries.

Do Shakespeare's Sonnets contain homoerotic elements?

Shakespeare’s sonnets are among the most beautiful expressions of love in the English language and most of them were written and dedicated from Bard to man. No one knows the identity of the beloved young man. Shakespeare’s dedication begins:
“To the onlie begetter of these insuing sonnets, Mr. W.H.”
The content of the sonnets is often explicitly homoerotic. For years he circulated “his sugred Sonnets,” according to his contemporary Francis Meres, only “among his private friends” in London. Meres seems keenly aware of queer culture in London then, publishing the rumor that Christopher Marlowe was “stabbed to death by a bawdy serving-man, a rival of his in his lewd love.”
Even after the sonnets were published, probably without his approval, for 170 years they were deliberately misgendered, changing the pronouns from “he” to “she.” In Sonnet 13, he is called “dear my love,” and Sonnet 15 states that the poet is at “war with Time for love of you.” Sonnet 18 asks “Shall I compare thee to a summer’s day? Thou art more lovely and more temperate,” and in Sonnet 20 the narrator refers to the youth as the “master-mistress of my passion.” The Bard’s poems evoke sleepless nights, distress and jealousy caused by his love for the young man.

Shakespeare’s sexual orientation, like many aspects of his life, has long been the subject of speculation and controversy. In 1954 C.S. Lewis noted that the sonnets are “too lover-like for ordinary male friendship,” though not the poetry of “full-blown pederasty,” and that he:
“found no real parallel to such language between friends in the 16th-century literature.”

Do Shakespeare's plays contain homoerotic elements?

Shakespeare’s plays also contain many homoerotic elements. Antonio’s unexplained sadness in The Merchant of Venice might be due to unrequited love for his young friend Bassanio. Another Antonio (in Twelfth Night), is willing to risk all for his companion Sebastian, the identical twin of Viola who, disguised as a man, works for Duke Orsino:
“I have many enemies in Orsino’s court,
Else would I very shortly see thee there:
But come what may, I do adore thee so,
That danger shall seem sport, and I will go”
Adding to the intrigue, the Duke is in love with Olivia, who has fallen for the transvestite Viola.
In Romeo and Juliet, Benvolio, who is clearly in love with Romeo, stands before him and says:
“be ruled by me. Forget to think of [Rosalind] … [Give] liberty unto thine eyes. Examine other beauties.”
Benvolio would be the only beauty in sight at that moment. It seems something may have been going on between the two gentlemen of Verona, too.

Did Shakespeare prevent his wife from controlling his London house?

Shakespeare spent much of his life in London, leaving his wife and children behind in Stratford-upon-Avon. In 1613, as Shakespeare was contemplating retirement to Stratford, he (and three other men who acted as trustees) bought Henry Walker’s Blackfriars Gatehouse for £140. The large house had long been a well-known refuge for persecuted Catholics. In Shakespeare’s Lives, Samuel Schoenbaum notes that the deal included:
“… elaborate arrangements, calling for trustees and a mortgage [whose] practical effect would be to deprive Shakespeare’s widow of her dower right to a third share for life in this part of the estate; for in a joint tenancy, Chancery would not recognize Anne’s privilege unless her husband had survived the other trustees.”

What's in Shakespeare's Last Will and Testament?

Not only did he intend to prevent his wife from inheriting his London real estate, Shakespeare left his wife the “second-best bed” in the will he wrote shortly before his death. No word on where the best bed went. Historians, without basis or precedent, try to convince us that second-best was really the best, because that would be the one they slept in. (This was first proposed in 1848 by James Halliwell-Phillipps, who provided flimsy evidence that has not since been improved.) The bulk of his estate was left to his daughter Susanna and her husband, Dr John Hall. As far as Blackfriars Gatehouse goes, he left the Halls:
“All that Messuage or tenemente with thappurtenaunces where-in one John Robinson dwelleth scituat lyeing and being in the blackfriers in London.”

Who was John Robinson?

The relationship of John Robinson (b. ca. 1656) with Shakespeare appears to have been more intimate than that of a mere London tenant. As far back as 1598, they were listed just two lines apart in the St. Helens (London) tax records, suggesting they were (or recently had been) close neighbors or lived together in the upscale Bishopsgate neighborhood before relocating—possibly together—possibly to the South Bank near the Globe Theatre (or maybe he used that as an address to divert tax collectors), and eventually to Blackfriars fifteen years later. In between them in the 1598 rolls was John Pryme, likely the well-to-do older (born ca. 1633) man who had brokered the 1579 mortgage for The Theatre, and a resident of St. Helen’s since before Shakespeare was born. It’s tempting to imagine that jolly threesome sharing a household.
John Robinson’s wealthy and powerful father lived nearby but had partially disowned his eldest son. John Jr. had something of a reputation as a playboy.
Both Shakespeare and John Robinson the Younger moved out of St. Helen’s around 1600, the year Robinson’s father died and Robinson the Younger lost access to a domicile next-door to his father’s. Robinson contested his father’s will, before and after the old man died. Nearly two decades later, John Robinson (the same man?) was in Stratford to witness the signing of Shakespeare’s will, a pivotal moment shortly before the Bard’s death.

Why did Shakespeare purchase Blackfriars Gatehouse?

Scholars have long speculated about why Shakespeare bought Blackfriars Gatehouse, which entailed a substantial mortgage of £60. Was it to provide a pied-a-terre for him to use during visits? An investment to generate rents? Meant to serve as a safe-house for fellow Catholics? The only confirmed motivation is that the purchase provided a place where John Robinson could live after Shakespeare left London. He resided in the Gatehouse during Shakespeare’s lifetime and for years following his passing, as suggested in Shakespeare’s will and likely with the blessings of the Bard’s daughter and heir, Susanna Shakespeare Hall. Perhaps Anne Hathaway held a grudge against John Robinson that motivated Shakespeare to keep the house out of his wife’s control.
It’s unclear if there were one, two, three or more John Robinsons in Will’s life—it was a common name—but it seems likely there was only one, with whom he had a long-lasting and intimate relationship that began soon after Shakespeare’s arrival in London, and extended beyond Will’s death, as his daughter’s London tenant.

Was Shakespeare estranged from his wife?

Shakespeare’s personal life paints the picture of a man who prioritized his career over his marriage, leaving Anne Hathaway behind in Stratford while he pursued a separate existence in London. In 1978 a letter was discovered, addressed to “Good Mrs. Shakespeare” who dwelt in Trinitie Street, London, leading to speculation that Anne lived for a time there with Will. The letter was from someone attempting to collect a debt from her husband on behalf of a young apprentice. Debt collectors often send letters addressed to the debtor’s wife, whether she exists or not, assuming that the husband will intercept it. It’s a great way to shake loose a payment from someone who wants to avoid further embarrassment. The letter establishes that Will lived on Trinitie Street for a time, but it’s not convincing evidence that Anne was living with him. There’s no particular reason to believe she ever even visited him in London, though Susanna did.
Their estrangement might have been exacerbated by religious differences; Will is speculated to have been Catholic, while Anne was likely Protestant. Susanna, their eldest daughter, may have adhered to her father’s Catholic faith.
Shakespeare’s will dealt another blow to Anne, leaving her little of significance and relegating her to an afterthought, while allocating funds for three London acquaintances to purchase “mourning rings.” His tomb’s inscription, which forbids its disturbance, may have resulted in a denial of Anne’s rightful place with him upon her death in 1623—a callous conclusion to their perplexing relationship.
FURTHER READING: MARSH, LIVING WITH SHAKESPEARE