Rating Cookie Run Ships. Why? Because I need to see who agrees with me.

Ancients.

Pure Vanilla Cookie Ships.

PV X WL: 2/10. After the Dark Enchantress Cookie thing, romance would be out the window. Especially after she tried to kill him multiple times. They can be friends, but I see them dating as an awkward thing. Even if she didn't turn into Dark Enchantress Cookie, they'd still be better as friends, or colleagues. 4/10.

PV X HB: 6/10. Hollyberry and Pure Vanilla Cookie are really enthusiastic, perfect leaders, and would definitely enjoy each other's company. Definitely got lowered after Pure Vanilla Cookie lied, but it was repaired after he admitted to his faults. If they dated, Hollyberry Cookie would be getting him drunk.

PV X GC: 5/10. Golden Cheese Cookie would definitely fly around with Pure Vanilla Cookie, but they make it better as friends to me. They would finance each other and rebuild broken areas(the Golden Cheese Kingdom).

PV X DC: 6/10. Opposites don't attract, but, they do work really well together. They are both good leaders, determined to do what's right, even when under pressure. The softie and the gigachad dynamic works decently for them.

PV X Black Raisin: 7/10. Black Raisin Cookie really trusts him as a leader, and would definitely die for him. 

PV X Dark Enchantress: -100/10. What the hell, enemies that try to kill each other is hella toxic, ew. Get it out of my face.

PV X Clotted Cream: 3/10. Clotted Cream Cookie is too into violent politics to have time for being peaceful.

PV X Custard Cookie III: -100000/10. Need I explain?

Crackships.

PV X Millennial Tree: 10/10. They would work together to make the world a better place.

PV X General Jujube: 8/10. Leaders together, strong.

I will not repeat ships I already did.

Hollyberry Cookie ships.

HB X DC: 2/10. They'd be friendly at one moment, the next, boom, she spiked his coffee and pissed him off.

HB X GC: 10/10. They both are party loving, friendly, happy go lucky, girl bosses. They have no downsides, and they'd likely have few disagreements except on serious stuff, since Golden Cheese Cookie is not serious.

HB X WL: 4/10. Still Dark Enchantress Cookie, who still tried to kill her twice. If not Dark Enchantress Cookie, they'd drink together 8/10.

HB X Wildberry: 0/10. Usually I'm fine with the bodyguard X employer thing, but Wildberry Cookie is basically her adoptive son, and that would not be good. Ew.

HB X DE: 0/10. No.

HB X any of her kids: -1000/10. Obvious reasons.

HB X Tea Knight: 8/10. They'd actually work well in the past, even until their old age, they'd be happy joking with each other and dueling dragons.

HB X Pitaya: 3/10. At first, I would rate it higher, but then again, they tried to kill each other in the past, though it's stopped, it wouldn't be fun to have brung up at Thanksgiving.

HB X Tarte Tatin: 8/10. The dragon hunters reunite, it'd work so well, and they'd love being together while doing it.

HB X Snapdragon: 0/10. C'mon.

HB X Royal Margarine: 4/10. The Rizzler would definitely annoy her after a while, but they'd be better off as friends.

HB X Clotted Cream: 4/10. Clotted Cream Cookie would be nice, but in the next moment, Hollyberry Cookie would think he's plotting something.