#hob hates shakespeare

[mxcat777]

So what if

Dream is sort of Shakespeare's patron, right? So would that make Shakespeare on of His™? And if so, would he reside in the Dreaming after his death instead of the Sunless Lands?

'cause if so. Consider.

He's still writing. (A lot)

He keeps up with modern literature, but keeps writing (at least mostly) in Early Modern English (that's it, right? Do I have my lit facts straight?). Imagine his recent plays littered with slang, disney references, (un)subtle references to shit that was based on his stuff that he either loves or hates, both are good.

He's kind of a favourite of Dream's. The same way Lucienne and Jessamy and The Corinthian are. He can get away with saying shit, because if he offends Dream he can turn around and start sprouting some poetry at that vain-ass bitch and all is forgiven. (In the worst cases it takes a new play about his royal majesty the Dream King and how generous and benevolent and regal he is)

Fishbowling happens, not sure what Will would do, the plot bunny didn't care.

Dream is back, all is well, he goes to the New Inn, Hob and Dream are now officially Friends.

They meet up more bc friends see each other more often than once a century. Oh yeah friends also know each others' names and such. So Dream tells Hob a bit about himself.

At some point he's like, hey hob u wanna see the dreaming?

Hob's like yES PLz??

Hob gets a tour, and from that point on usually gets the option at night to dream normally or visit the palace.

On one fateful night, Hob decides to take a stroll through the library, goes looking for Marlowe's shelf, because he kind of wonders what other stuff that genius would have written had he lived longer.

Only to (maybe literally) bump into, you guessed it, Will Bloody Shaxberd.

He stares.

Will goes 'hey'.

And then Hob goes somewhat feral.

(no he is not over it, sue him, he's allowed to hold a grudge.)

He goes off on a rant about, see, ofc ur still plagiarizing marlowe he was so much better i can't believe dream left me for you you useless twat you couldn't write shit without him so why did you get the fucking privilege of living with him and knowing him for fucking centuries i had to fight 600 years for his bloody name and i'm guessing you got it right that first meeting hm?

And Will goes oh shit it's you! And then cuts Hob off with a "you're so right! I was an absolute shit playwright before your friend helped me!"

And Hob is... Understandably lost. This was not how it went in his head.

And then Will continues, I was so nervous the time right after that meeting, I knew he was some sort of supernatural being, no clue what though, he's really not good at introductions, is he, so I sort of assumed you were too, and I was waiting for your revenge for stealing your date away, recently found out you're actually human, albeit immortal, and it was not a date, though, speaking of, have you sorted yourselves out yet?

And Hob, quite understandably even more baffled, sort of gapes for a bit.

Before very nervously denying anything of the sort.

Will just stares.

And goes, bruv, you weren't subtle then, still aren't now, spare everyone else the UST, please, for the love of god, you two need to fuck post haste.

And Hob is like, hahaha, eh, yeah, nope, fun seeing you, BYE.

So Will sighs. And goes to see Lucienne, as any sensible person would.

Lucienne sighs as well. At which point Will steps to Dream himself.

"My lord?" "Yes, William?" "Forgive my directness, but so as not to risk any misunderstandings, what exactly is your relationship with Hob Gadling?" "We are friends. Why do you ask? Is that not clear?" "Well, to be perfectly honest, m'lord, I assumed you were... Involved™." "We are not." "But you'd like to be though, right?" "You dare presume to know-" " I dare presume to know what attraction, romance, love, all that looks like, sire. I must do, after portraying it in my plays for over four centuries. After writing several hundreds of sonnets on the topic." "I-" "In my humble opinion, my lord, it is a good match. He understands you, you continue to fascinate each other, he can provide a safe place where you need not be monarch for a moment. And of course, you are quite obviously attracted to one another sexually." "WILLIAM SH-" "Oh calm down! I'm certainly not judging either of you!" "...he is attracted to me?" "..." "Is he?" "YES! Lord give me faith! Kiss him! Go to him and teleport the both of you onto a bed! Or if you want to be sappy go slow and bring him a rose, but please, for the love of the collective sanity, do something!" "But how do you know? What if you misunderstood? What if it is unwelcome? I cannot lose him!"

At which point Will turns around, leaves the throne room, goes back to the library and rant to Lucienne

"I swear I'm going to write a play about them, just to point out how stupid this is. I feel compelled to call it a tragedy, but I think it needs to have a happy ending, otherwise Lord Broodphius would get stuck on the but what if it does end in tragedy, so I suppose a comedy would be fitting, but then again, this is too painful to watch to qualify as a comedy. Tragic comedy? Comic tragedy? I'll figure it out..."

And Lucienne is like, if you'd like to perform it properly I'm sure there are a few dreams who would be more than willing to help out, take on a role.

Hob comes back to the Dreaming a few days later and finds Will up to his elbows in paper, reference books, thesauruses and rhyming dictionaries (handy things those), and empty mugs and the like.

Will looks up, somewhat manic, and is like, Hob! Great! Just the person I wanted to see! Would you help me, please?

Hob's like, sure? Kind of apprehensive, but he gave everything some thought and decided that as long as he could go on dunking on him, he could let go of most of his jealousy (cuz that's what is was, he's mature enough to admit)

Will goes, Awesome! Tell me about you and Morphius! How do you see him, what's your story, I only ever get bits and pieces from his lordship, so I'm in severe need of some context...

And Hob is somewhat suspicious, but he indulges him, and really, telling the story comes too easy, so he gets into it completely and doesn't even notice when he starts slipping into rants about Dream, about how beautiful, and magnificent, and misunderstood, and kind, and way-out-of-his-league-but-god-dammit-he-went-and-fell-in-love-with-the-bastard-anyway he is

And Will takes studious notes.

And then goes like, so some of the sonnets I've written were with you two in mind, you wanna give me some feedback? (Ahem, sonnet 24/29, some others work too, undoubtedly, but I am no Shakespeare expert, unfortunately)

And he does something similar with Dream, maybe citing Hob's dislike of him as the reason he wants to know more about him without having to bother him overly much, like, I want to set things right between us, but I need to know more about him to do that, will you help me, m'lord

And he does

And Will just sits back and takes notes as Dream also spirals into a passion fueled rant about Hob

And all those notes end up in the eventual play

Auditions for the roles happen when Dream and Hob are out on a Not Date™ in the Waking.

There are surprisingly many auditioning for Hob's role, and surprisingly little for Dream's

Until Will points out that Dream would probably be more offended by an unworthy portrayal of his Love that of himself, at which point some of the dreams bow out entirely, bc Will knows how vain their lord is, so they decide not to risk unmaking and tactically retreat

Will is in his fucking element, it's been way too long since he's properly directed a play!

Eventually Will comes up to the Mutually Pining Idiots like, hey m'lord, Hob, I've written a new play, and I've been working with some of the dreams to make it happen, do you want to see??

So they watch. They watch as two absolute fucking idiots stumble around each other, everyone on and off stage can see how stupidly in love they are except for them, and both start sweating profusely when they start recognizing their own words quoted back at them.

The end of the play is something of a direct call-out and a plea from the dreams to please just talk to each other, fuck and get married, preferably in that order, but they're not picky.

Then everyone leaves them alone for the Conversation that is most likely going to happen.

Will stays behing hiding unobtrusively in the shadows tho.

He's not about to let all his work go to waste if these idiots ty to play it off again. He will lock them in a broom closet if he has to, watch him.

They don't.

Luckily.

There are like three sentences total spoken. Then they're aggressively making out.

Will leaves the room very content about his matchmaking skills.

And hey! He got a good play out of it, if he does say so himself!

[sweetdreamsaremadeofsugar]

Hob wrote this song and sings it around Dream all the damn time.

[llflorence]

White Knight - Dream of the Endless / Modern Hob AU by LLflorence on AO3

“I wish to understand,” he began, pausing to side-eye his sister before laying a chilling gaze on Hob, “your enthusiasm for philosophy. Discuss the great teachings, and the modern interpretations of the masters of stories. Plato. Emerson. Shakespeare –”

“Oh,” Hob nearly choked on his drink, wiping the froth from his upper lip and chuckling slightly. “I detest Shakespeare.”

[notallsandmen]

Reading up on Christopher Marlowe, and found out that he died at the mere age of 29 under mysterious circumstances: during some kind of brawl, Marlowe was stabbed above the right eye, killing him instantly.

Marlowe was considered the foremost dramatist in London in the years just before his mysterious early death in 1593 (4 years after the Dream’s and Hob’s meeting in 1589), after which Shakespeare succeeded him as the pre-eminent Elizabethan playwright. Are we sure that Dream merely commissioned two plays from Shaxberd and not just, you know, asked the Corinthian to shiv his strongest competitor? 😂

[shipsgaysfordays]

okay but how would hob gadling react to the song “hard to be the bard” from something rotten

‘cause my first thought is that he would be seething but like i could be wrong

[lady-of-the-spirit]

I've said this already but I don't get how "Hob hates Shakespeare" became a whole fandom headcanon when canonically all Hob said about Shakespeare is "that lad, Will Shakespeare, turned out to be a half decent playwright after all", said with a smile, and that people are idiots for changing his endings.

[freytful]

“Hob hates shakespeare” is the most baffling piece of fanon ive seen in a while bc like ??? It’s explicitly against canon and makes him seem insanely petty. Is the idea that he saw that production of King Lear time in 1789 and was just seething the entire time about losing a date 200 years earlier? You think he’s that petty?

The joke isn’t that he hates shakespeare the joke is that its 1589 and shakespeare hasnt written anything good yet. what. 

[jackdoesstuff]

WHO IS DREAM?? WHO IS HOB????? WHY ARE THEY UNDER THE SOMETHING ROTTEN TAG ABOUT GOD I HATE SHAKESPEARE?! SOMEONE EXPLAIN PLEASE

[regina-cordium]

i have two VITAL questions

1) would hob be into musicals

2) what would his thoughts on “something rotten” be

[valiantstarlights]

Which Hob Gadling Are You? Quiz

Instructions: Get a pen and paper (or open your notes app) to keep track of your answers and scores. Select one response and add +1 to your tally. At the end, the letter with the most number of tally marks is your result. There are 8 possible results, as there are 8 versions of Hob. Enjoy! 😊✨

--

1.) How well do you flirt?

Not sure. There's no one to flirt with. (A)

Fucking terrible. (G)

Not trying, not interested. (E)

Somewhat of a disaster, but I'd like to think there's hope for me. (B)

Not sure. I think I'm decent at it, but... (C)

I'm often not sure if I'm being flirted with, but if the person is my type, then I'll do my best to flirt back! (H)

I know what I'm doing, and hopefully it's my date tonight. ;) (F)

Honestly? I'm at a point in my life where I don't care if I'm good at flirting or not. (D)

2.) How much do you wanna fuck/get fucked by your date?

0% - Not right now. I have other priorities. (E)

25% - I'm not actively thinking about it, but if they're interested, then I'm game. (B and D)

50% - Why not? My date is super hot and I'm very interested in them. But if they're not in the mood, then that's fine, too. (H and C)

75% - Look, I'm making an Effort here. It would be nice if my date could show some interest. (G and A)

100% - OH HECK YEAH (F)

3.) Finish the sentence: "How..."

did you know that I'd still be here? (B)

long should I wait? (A)

did you know my name? (H)

wonderful to see you again. (D)

the hell did I fuck that up? (C)

rude! (G)

do you want me? ;) (F)

much longer until my order gets here? (E)

4.) Pick one word from the list:

Life (E)

Patience (A)

Change (F)

Courage (H)

Wonder (B)

Contentment (D)

Friendship (C)

Prosperity (G)

5.) Do you hate Shakespeare?

Ugh. Do we have to talk about him? I have more important things to worry about. (E)

I'm so glad you asked. Here, make yourself comfortable. I have a 6 hour presentation on why he sucks. (D)

I'd rather read a phonebook. (A)

I don't know who that is. (B)

(sighs) If I say no, will you leave me alone? (C)

THAT FUCKING BASTARD (G)

I watched one of his plays. Still think he's overrated, though. (F)

What's a shake spear? Is that a weapon or something? (H)

6.) How likely are you to say stupid shit?

Everything I say is stupid shit. (G)

Only when I'm drunk. (H)

I have no filter, so... (B)

I'd like to think I have learned not to be so careless. (E)

Fuck! I thought I had it! Apparently not. Gods motherfuck I'm never speaking again. (C)

I'm trying, okay? I really am. (F)

I said stupid shit once and I regret it until now. (A)

Very likely. Just wait and see. Any second now. (D)

--

YES OR NO QUESTIONS: If your answer is yes, +1 to the letter indicated.

7.) Do you believe in love at first sight? (H)

8.) Do you get excited over things/topics that others consider boring? (B)

9.) Are you content with the life you have right now? (G)

10.) Do you still feel hopeful, despite the horrors? (E)

11.) Are you always DTF (Down To Fight)? (F)

12.) Have you ever fallen in love with a friend? (C)

13.) Would you wait/Have you waited for hours for your friend/s to arrive? (A)

14.) Are you willing to wait however long it takes for the love of your life to appear in your life? (D)

--

15.) BONUS: Which is your favorite Hob?

1389 (H)

1489 (B)

1589 (G)

1689 (E)

1789 (F)

1889 (C)

1989 (A)

2022 (D)

--

RESULTS:

Mostly A's = 1989 Hob

Mostly B's = 1489 Hob

Mostly C's = 1889 Hob

Mostly D's = 2022 Hob

Mostly E's = 1689 Hob

Mostly F's = 1789 Hob

Mostly G's = 1589 Hob

Mostly H's = 1389 Hob

[q-ueen-potato]

So....I did a thing

Aziraphale and Crowley 'kinda' adopt a young Hob Gadling when his family gets wipped out by plague/war/famine. And share custody while he grows and they continue to get their own personal sh*t together.

In his mid 30s, Death turns up with a request for him to be a friend/ share some of that family love for life and humanity with her little brother. Possibly don't mention the angel, demon legal gaurdian thing just yet though. Here's the plan.

Cue a complete shift in power dynamics where Hob knows all about the supernatural world and who Dream is. He's just waiting for the right moment to tell him. He was going to in 1889 but that did not go as planned. Aziraphale and Crowley remain alarmingly concerned about the entire thing but are good supportive dad types.

When Dream gets captured Hob comes to the rescue with a whole host of Gaimon verse back up. With a, 'Surprise! Please don't smite my parents. Tah, love you.'

[moonriselabyrinth]

Okay I’ve seen the whole thing of Hob bashing Shakespeare in lectures out of jealousy thing a fair few times but my favorite idea I’ve gotten from that is when he does it he starts off real strong “I fucking HATE Shakespeare” and everyone is like “whoa 😳” this guy has strong feelings about Shakespeare’s work and he spends the whole lecture bashing Shakespeare but he never brings up his actual writing or really the substance of his work past something like “and really he didn’t even have any good ideas in the first place” or something vague like that so all the students are left wondering what the fucking point was and why he seems to have such personal beef with William Shakespeare.

[thenightling]

You know, The Sandman Netflix series using the song "Shattered Dreams" by Johnny Hates Jazz for the scene when Hob realizes Morpheus has "stood him up" seems to accidentally foreshadow something hinted at in The Sandman: The Wake.

"You said you'd die for me." is said at least twice in the lyrics.

One prevailing theory about Morpheus's death is that he is now spending his afterlife in Hob's dreams as a dream entity.

For starters "It's never just a dream." is said repeated in The Sandman. And that was even Neil's response when asked if Hob's dream is more than just a dream.

We see Destruction in Hob's Dream and Destruction really was visiting The Dreaming during The Wake.

The dream is set on a shoreline and in The Tempest Morpheus says to Shakaspeare that unlike his Prospero character that he (Morpheus) would never escape his Island. In Shakespeare's The Tempest play the sorcerer Prospero destroys his magical tools to escape his island that he had been trapped on.

Morpheus surrendered his power and tools to another aspect (piece) of Dream of The Endless, Daniel.

Hob had even previously said that he keeps people alive by remembering them- by dreaming of them.

Hob is immortal and will live indefinitely. So long as Hob refuses to die, there will be someone who would definitely dream of Morpheus, giving him reason to exist as a dream entity.

As Dream of The Endless Morpheus is dead but as a dream entity he is free.

And he chose his afterlife in the dreams of his friend.

"You said you'd die for me."

[delta-pavonis]

Ficlet: O that I were a glove upon that hand

Dreamling || Human AU || Rated E || ~1100 words

(Because Tom doing Romeo at VogueWorld 2023 gave me some feelings and Ferdie is often in his Venice Preserv'd look in my head... although with longer hair.)

This has, perhaps, gone too far.

Let's back up.

Everyone in the department, most people on campus, and – because of a viral video of him going off at the director during a dress rehearsal of a Shakespeare in the Park performance of A Midsummer Night’s Dream – a damned large swath of London all know of Dr. Robert Gadling's particular and peculiar hate of the Bard. It is what makes this whole thing incredibly frustrating.

Gifts. Hob has been getting gifts. Left for him in conspicuous places, each more finely crafted and expensive than the last. And each with a goddamned Shakespearean love sonnet on it.

If it wasn't for the nature of the gifts themselves Hob would be absolutely certain someone was taking the piss. (Jo, that would probably be Jo.)

But each gift is so bloody thoughtful; carefully chosen with an uncannily tuned awareness to Hob’s personal needs and tastes. This person either really cares for him or… well, he would think the person a possible stalker except that everything they have done relates to something that has happened in public, with full easy access for many people to make a judgment that Hob likes or needs something. 

There have been six of them now. And aside from the fact that Hob’s living room wall now looks like all those movies where the authorities are frantically tracking a serial killer, complete with a map of London and lots of red sharpie, he is rather… flattered? 

It has been a long time since… well. The anniversary of Eleanor's death will be rounding on eight years this winter. 

Hob thinks he has worked out a pattern to when he gets the gifts, is like 80% confident he can guess when they have gotten placed in each location, from his university office, to the men’s dressing room at the White Horse Community Theater, to his usual table at the New Inn. Add to that his approximately 60% confidence in the reasoning behind the temporal spacing of the gifts, and he is ready to roll the dice.

He locks up his office a tick early, as usual on Thursdays, and makes all appearances to head home before going to that evening’s rehearsal. But as soon as he gets home he is donning a new hoodie no one has seen him wear before, slinking back out the garden door, over the hedge, and jogging to the theater. Hob closes himself into the darkness of the men’s dressing room a solid two hours before anyone is scheduled to be anywhere near the place. 

And he waits. 

Hob is good at waiting.

He is crouched where he will be behind the door when it opens, but this puts him immediately next to some of the accessories storage for costuming for this show. And oh, they have gotten in a new pair of leather gloves for him.

Just because he is good at waiting doesn’t mean that he never gets bored. 

Hob slips on the new gloves and works his hands in them. These will be perfect to swordfight in, fantastic.

And then the door creaks open. 

He freezes and watches, only the sliver of light coming from the hallway to help him. A masculine figure, slim, in a peacoat, walks silent as a hunting cat to the second chair from the far wall, just where Hob usually gets ready. 

A hand runs softly across the back of the chair once before a small box is left on the tabletop. Then as quietly as they came in, the person turns to leave. 

Just before they get to the open door Hob pounces.

There is a shout and a scuffle, the two men – for it is another man, of that Hob has no doubt – grappling as one tries to escape and the other hold on.

Which is how Hob ends up with his black leather-gloved hands wrapped around the pale swan neck of his longest friend. 

They haven’t seen each other in… fuck, it feels like more than a hundred years. And they had not parted on good terms. 

“Christ, Dream?” Hob pants out the nickname but does not let go. 

Diamond-sharp blue eyes that could belong only to one person stare at him from beneath heavy lids. He parts his lips to speak, but at the same time Hob shifts the grip of his hands and any words Dream was going to say get lost in a breathtakingly thready moan. 

Barely a heartbeat later they meet in the middle, Hob’s hands going to the back of Dream’s head and Dream’s arms going around his shoulders and their mouths fit together like goddamned puzzle pieces and Hob knew, he fucking knew, it would be like this. 

They knock over no less than two chairs, collapse against a wall for a minute, then one of them pushes off and they are almost going ass over tea kettle onto the couch. A bit of quick footwork on Hob’s part and they are on the opposite side of the room.

By the time Hob has Dream sitting on the vanity they have gotten their shirts off and his bare back slams into the mirror’s surface, sliding and squeaking with the thin sheen of sweat. He gets his hands under Dream’s thighs, hikes him up to grind their clothed erections together, and once Dream has his legs wrapped around Hob’s hips he brings one hand to his mouth to pull off the gloves.

An unsteady hand grabs his wrist. “Leave them on.” Dream’s voice is even lower than Hob remembers it. 

There is fumbling to get flies open and then Hob has his hand wrapped around both their cocks and is pumping. Dream’s fingers are now tugging on Hob’s hair, his body arching prettily as Hob gets his lips and tongue onto that beautiful neck.

Hob is about to be embarrassed by how quickly he is nearing completion when Dream pulls him into a kiss, moaning into his mouth as he shudders through his orgasm. 

“Come with me, Hob,” is whispered against his lips and Hob is absolutely lost to it, shouting into Dream’s collarbone.

They are still panting, large heaving breaths, when Dream tugs Hob’s hand up from where it is wrapped around their spent pricks so that he can lick the leather clean. Hob watches that pink tongue dance between his fingers and his cock almost twitches in interest. He huffs a laugh and takes Dream’s chin in his grip, pulls their mouths back together so that he can speak against them. 

“Hello, Stranger.”

[gabessquishytum]

a book club AU where Every month, Morpheus and Hob attend the same book club and get into debates over the meaning of the book and every meeting turns into their personal vanity quest trying to impress the other with their wit.

And the other members dont mind because they just want them to kiss already because it is so clear Morpheus and Hob want to.

Amazing, incredible, revolutionary, I love it.

I’m imagining that Lucienne runs the book club and drags Dream along because he’s in his post-divorce emo era. Other club attendees include Matthew (showed up once to impress a girl, keeps coming back for the gossip), Gilbert (always makes everyone read G K Chesterton when it’s his turn to pick a book), Cori (local serial killer who reads crime novels for inspiration), Gault (Lucienne’s gf, there for emotional support reasons). Hob is a reasonably new member who just moved to the area.

Hob thinks Shakespeare is overrated, Dream hates “trashy” literature. They clash immediately. Hob calls Dream an elitist snob and Dream says that he’s proud to be a snob about literature, actually. They’re already secretly in love with each other.

The arguments are like foreplay. They sit opposite each other in the little circle of attendees and have the silliest little debates and arguments about the content of each book. Of course they don’t totally dominate the entire time, but everyone else is honestly looking forward to the inevitable cat fight + eye fucking sesh that is bound to happen at every meeting.

There is absolutely a betting pool going on where everyone has guessed when they’ll finally snap and make out in the middle of book club. And then Hob turns up in a suit (he apparently came straight over from an important meeting) and Dream’s jaw drops. He’s never been able to resist a well dressed man, and several months worth of sexual tension kind of… explode.

Lucienne happily pockets her winnings (she might have had something to do with Hob showing in the suit…). Honestly she deserves it, with all times that those two clowns have disrupted her book club!

[achillesuwu]

Let's talk about Shakespeare, The White Horse and how important they are to understand Dream & Hob's relationship.

As much as I love the "Hob hates Shakespeare" headcanon, it isn't how I saw Hob reaction in 1589.

Like for me, Hob thought "Eh, whatever" at the end of it which is SO important.

Hob, at that point, thought that Dream didn't really matter. He didn't think he would lose his son and his wife. That Hob (and still present Hob btw) thinks that he got his immortality simply because he didn't want to die. THAT is the reason why he got married and had children.

Did 1589!Hob want to impress Dream? Yes.

Does he want to impress DREAM? No. He want to show off. If Dream was any other supernatural being it would be exactly the same to Hob.

1589 Hob thought "Eh, whatever, he may be the oldest dude I know now but I have an immortal wife, an immortal son. Everything will get better and better. He doesn't matter."

Everything that happens in the 1589 meeting and after lead them to understanding what they mean to each other in 1689.

That 1689 meeting isn't only about "Dream begins to really care about that human, to see him beyond an interesting toy", it's also "Hob learns that if it was that easy to convince people that they don't have to die there would be more immortals than him & Dream*. He learns that he will continue to lose people, he learns that sometime life will just get worse and worse BUT Hob also learns that Dream will be there along the way. He won't lose Dream even if he displeases him, even if he has nothing to his name. Dream became important, he matters because Hob knows he will be there [in the white horse]. " it's them beginning to care beyond the " he is a random human" & "he is a random stranger."

(*this is important for later. )

We can see it in 1789 too, their relationship developing even further. Hob is annoyed that Dream judges him but it isn't like 1589. He doesn't just want to impress him to stroke his own ego. He doesn't do his 1589!"Eh, whatever" because Dream's opinion matters to him now. If it was someone else it would be different, I don’t think he would have really thought about it. I even bet that like many time in history (and now) Hob knew but just didn't care enough to do anything. Hob doesn't talk about Shakespeare (+joke about Dream being the Devil) because he is jealous but because it could be a shared joke between them. Hob does a bit want to reassure himself that Dream will still be here but that isn’t really what he is aiming for. Now, Hob to wants them to be close. That is the reason why he choose Shakespeare of all things, because he wants to reassure himself about the fact that he knows Dream. That he is right about what he knows about him (it’s a bit about him being right about believing that Dream won’t leave but not just that).

Hob talking about Shakespeare create a link between 1589 & 1789. In 1589 Shakespeare is what Dream use to separate them. In 1789? Shakespeare is what bring them closer. Dream doesn't leave when he disapprove Hob's choices, Dream tell him he can go back to being a great story. Which mean Dream trust him to make the right choice. This reassure Hob on their relationship and it's why their act like complete bestie (with sexual tension) after. The look™ they give each other when Johanna appears. The "you look worse" and their inside joke of Dream not being a devil but people thinking he is, them acting like a team and mutually protecting each other,... They are closer than before but they are not too close either. AND They do not leave the white Horse.

Now let's talk about 1889 but more importantly about the other immortals Hob knows (he talks briefly about them in the comic, he knows that there are other humans immortal, he encounters vampires at some point & he must know about mutants since they are in DC universe). The fact that Hob knows them but doesn't seem to care that much to go talk to them solidifies the fact that Hob changed his opinion on their relationship again.

Dream doesn't matter to him like he mattered in 1689 or in 1789. It isn't because he is going to be there. It isn't because Hob knows that he is right about Dream always coming back to him.

I don't even think that Hob conscientiously knows it at that point (1889) but it has NOTHING to do with Hob being ‘lonely’ and Dream being immortal and the ‘only’ option available to be friend with. Nor Dream being a constant. Hob could find others immortal. Hob could find others constants. Yes, I'm talking in plural. Hob is choosing Dream even when he has MANY options but that mad man does NOT want those other immortals anywhere close in his life. Hob thinks he is lonely but he isn’t. He is moping and sulking because he wants Dream.

Dream is important because Hob likes him, and it completely change Hob's attitude. In 1789 he didn't seem to be really really annoyed when he didn't get his answer. Johanna interrupting their meeting was meet with Hob (and Dream) making jokes. It was something interesting, something funny. In 1889? Oh boy, Hob doesn't just want to see Dream "along the way", he doesn't just wants to get "close", it isn't about the lack of answers. He managed just fine for 5 centuries. No, it’s what the lack of answer MEANS. Hob wants Dream to admit that he likes him back, he wants to matter like Dream matter to him.

You know what I was saying about Hob not conscientiously knowing that it isn’t about Dream being immortal or a constant but about Dream not admitting that he likes Hob? Well, Hob says it a bit in 1889 " if you here then too is because we are friends, no other reason ! Right ? Fuck.". Hob doesn’t even acknowledge that Dream imply that he won’t be there next time. He doesn’t care about that (and/or he thinks he knows Dream well enough to know that he will be there no matter what) but I don't think he really understand why he doesn't care about it.

Edit : notice how 1889 is the first time Hob meet Dream nearly outside of the White horse? How it's the first time he get out of it? Their relationship is changing.

However, I think it’s in 1989 that Hob is forced to face it because it removes everything that mattered before.

As far as he knows Dream sticks to his words and will prove him wrong. There is no more constant immortal fellow coming every hundred years. It's just him alone. The pattern is broken, Hob lost his constants. (but it’s interesting to see that Hob is ready to get back on it (Shakespeare is implied there btw ‘I’ve seen plenty of friend get in fights in pubs. Even more of them laugh about it later.’) when he says ‘maybe another hundred years’. He tries to cling to his belief in what he knows about Dream (that he will always come back to the white horse).).

The lost of his constants are symbolized by the white horse getting destroyed/abandoned but more importantly it forces him to acknowledge that they don’t matter and he don’t want them. Hob doesn’t go in the white horse every hundred years because of constants. If he did it shouldn't matter that Dream isn't there but it isn't the case and he knows it. He goes because of Dream, because he likes him. That place is only important because without the white Horse he may never see Dream again. The date is only important because it's the day they met.

For Hob, in their relationship, constants are irrelevant, when is irrelevant, the place is irrelevant. Only their friendship is relevant. What Hob wants is Dream to be his friend. He doesn’t want to keep their one hundred deal nor does he wants anyone else other than Dream to be there. That's what Hob learn in 1989.

THAT is why Hob wrote in red ‘New Inn’, why he didn’t renovate the white horse, why he was waiting 30 years later, why Hob isn’t angry at Dream for being late. Hob wants to break their habits and create new one (which they do since in non-filmed part of the script Dream visits him in his University)