This is canonically what happens to Molly in between adwm & ahwm (in a linear project standpoint at least)
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This is canonically what happens to Molly in between adwm & ahwm (in a linear project standpoint at least)

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Mark, trying to swing a GoPro partnership: You remember the van vlogs, right?
Mark, why do you hurt me, sir?
Like I seriously cannot overstate how much pure serotonin those van vlogs give me. idc what Mark's opinion on them is, van vlogs my fucking beloved
van vlogs
happy three year(ish) anniversary to the Barrel and mark’s van vlogs, rest in pieces
Van Y/N: Sometimes, I don't realize an event was traumatic until I tell it as a funny story and notice everyone staring at me weird

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What about... Capt. Magnum fathering Y/N?
Send me an ego for Captain Magnum to be a father figure to, and I will give you headcanons!
Sure thing! I’m gonna split this up into three parts for three different kinds of Y/Ns!
Heist, Pirate!Y/N
It feels like seconds, but you spend years on Captain Magnum’s ship.
You eventually become First Mate and he is rearing you to become the next Captain of his ship. If you all survive that is.
He has a lot of faith in you and your abilities, hence why he is giving you such an important role on the ship.
He personally teaches you everything you need to know about running a ship with a firm and guiding hand the entire way.
He was almost disappointed after you mastered navigating. It was a good excuse to just spend time together and look at the stars. Sometimes at night he’ll still hang out on deck, looking up at the stars. hoping that you’ll join him.
He was very proud of you after you had your first kill. He took the nicest hat that he could find, and put the most gaudy feather in the world in it to congratulate you.
It doesn’t matter how bad you are at singing. He swears that you have the voice of the loveliest siren out there. He INSISTS that you sing whenever a song breaks out.
He would take a bullet for you. He actually has.
But most importantly, he respects you and your desires. He doesn’t push the matter further after you decide not to call him ‘daddy.’ (He’s a little hurt, but he understands.) You can leave the ship whenever you want. If anyone tries to hurt you mentally or physically, he would crush them in his muscles until their head popped off.
Normal Y/N
Captain Magnum gives the BEST hugs! He probably could crush you, but is very careful not to. He is a big, warm softie towards you.
He would be very happy to give you a piggy back ride if you asked. However if you do so, you WILL smack your head against the ceiling.
The Barrel practically buckles under his weight. You worry that he’s gonna break it, but she hangs in there.
He’s weary about this Mark guy you keep hanging out with, but is ultimately supportive of whatever relationship you have with him. However in private he has threatened Mark on several occasions. (Standard, “If ye hurt a single hair on Y/N’s brow, I’ll bury you at sea,” kind of stuff.)
He REALLY wants to take you and your friends out on his boat sometime. Why go on a cruise when you can do so much better on his ship, right?
He loves going fishing with you. He knows that it’s not always the most exciting thing in the world to do, so always brings a few things to keep yourselves amused in the down time. Cards. An instrument. A radio. One time he even tried to bring a TV and a game console, but you managed to talk him out of it.
He absolutely lets you have booze, even if you’re underage. He does stay sober during this and makes certain that you’re safe and not doing anything too harmful to yourself while drunk.
If you have a disability, he is doubley supportive of you. He doesn’t have legs. he gets the struggle. He just wants you to be happy and healthy in whatever way that you can.
District Attorney Y/N
If he meets you before Who Killed Markiplier he thinks that Damien, WIlliam, Celine, Abe, and Benjamin are all good catches. He absolutely thinks that you should go after whomever you prefer in the bunch. He is suspicious AF towards Actor!Mark, but doesn’t judge if you’re into that sort of thing. Also he is very proud of you becoming District Attorney, but constantly asks (in a joking manner, you hope) if you would let him get away with a little murder and looting. (Time is weird in WKM. He may be from the Golden Age of Piracy, but there’s still a possibility of you meeting him.)
Otherwise, after he learned that someone was trapped in the mirror, he made it a habit to visit it to try and talk to you. Dark isn’t too pleased with this, but Captain Magnum isn’t too worried about the grumpy 3D man.
He has taken to reading books out loud to the mirror, hoping that it’ll offer a small distraction to whomever is trapped in there.
He keeps a small guilded mirror on his belt, hoping that you can move from the mirror on the wall to this other one. He thinks that it’s a real shame that you have to be trapped in that dusty old mirror on the wall. He tries to dust it and keep it clean, but it’s a little difficult to polish that mirror without ruining whatever you’re trying to clean it with and cutting yourself. He keeps this pocket mirror super clean and polished though. Just in case.
He would be overjoyed to know that his efforts aren’t in vain. It may be difficult to communicate to him when you’re stuck in a mirror. But if you do it, he will do everything with even more gusto.
If the District Attorney manages to get out of the mirror, the first thing he will do is squeeze you in the biggest bear hug that you’ve ever experienced. Is that your spine breaking? Probably. Feels like it! This is fine. It’s fine. You don’t need a spine.
My version of Y/n!! Idk if I'll ever name them or just keep them as Y/n!
RIP The Barrel, you will be missed.