For optimal gift giving options you can give Clint the following gifts:
Quartz: Can be found in the Mines and the Skull Cavern
Salmon Berries: Can be found during the spring time while foraging, usually found growing in the bushes
Wild Horseradish: Can be found in the spring coming out the ground

However if you would like to give Clint his most hated gift you can give him a Holly, a plant that can be found in the winter foraging but its more optimal to give the other gifts for the sake of time unless you happen to be very patient and are willing to wait til winter for the Holly's.

=====SPOILER WARNING AHEAD DO NOT CONTINUE IF YOU WISH TO EXPERIENCE THE HEART EVENTS FIRST HAND====

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So assuming you either don't care about spoilers or have already experienced the heart events you can ruin Clint's love life:
Based off the social interactions you can have with Clint you will notice he has a crush on Emily, this is where we weaponize his own love life against him.

1. To build friendship with Emily the quickest you can give her the following items
Gems: list includes Amethyst, Aquamarine, Emerald, Jade, Ruby, and Topaz which can all be found in Mines or Skull Cavern
or you could give her Cloth, Wool, and Survival Burgers but you are most likely going to end up giving her Gems since you are frequently going to find them while in the Mines or Skull Cavern

2.After you build friendship with Emily make sure you get her all the way to max hearts which is 8/8, making it able to date her if you give her a Bouquet which can be bought at Pierre's shop once you receive a letter from Pierre telling you it's for sale

2.5. This step is optional, and serves no purpose to helping you take one step closer to achieving your goal of making his life a living hell it's just funny to point and laugh at him. Once you obtain 8/8 hearts wait until Emily sends you a letter in the mail regarding clothing therapy and attend the event at Mayor Lewis's house at 10 AM. From there you can watch the heart event and point and laugh at Clint during the cut scene, just sit back and watch everything unfold.

3.This final step's timing is optional unless you want to go the full mile, once Emily becomes your girlfriend max out the remaining 2 hearts that unlock so you can marry her. To marry Emily you must first have repaired the wooden bridge located at the beach to the right, it requires 300 pieces of wood to repair. Repairing the bridge unlocks the Tide Pools area and during rainy or stormy days the Old Mariner will show up and will sell you a Mermaid Pendant for 5000 only after you max out friendship at 10/10 hearts. From there you can give Emily the Pendant and she will become your fiance and you will have your marriage ceremony in 3 days and this is where the optional timing comes in.

3 (If you decide to follow timing). Clint's birthday lands on the 26th of winter, and the marriage ceremony takes 3 days to set up, if you are patient enough to wait until winter you can give Emily the Mermaid Pendant on the 23rd of winter and watch the ceremony take place on the 26th of winter, forever reminding Clint on his birthday that you married the love of his life on the same day forever.
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(NOTE THAT MY TIMING COULD BE OFF AND YOU MAY HAVE TO MARRY EMILY ON THE 22ND CHECK CALENDAR IN GAME ON THE DAY YOU CHOSE TO MARRY HER TO SEE THE EXACT DATE THE CEREMONY TAKES PLACE, IF YOU MESS UP LEAVE WITHOUT SAVING)
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Although the rest of these things you can do are no where as time consuming as the ones above these will still make Clint's existence a pain.

Additional gift options: For the winter star secret gift exchange you can give Clint Garbage, which can be fished up easily in most water sources. you can also give him the same gift for his birthday that perfectly represents him as a person.

Bombs: When you acquire the slingshot you can also buy explosive ammo for it, with this power you can simply hunt down Clint and shoot him endlessly with explosions, which lowers friendship with each shot but you are out to ruin your friendship with him or even stop it from starting.


Hopefully you find this guide useful for making this guys life a living nightmare and this is my first and only guide I will ever do. AND TO ALL THE CLINT FANS OUT THERE GET A BETTER PERSON TO SUPPORT.