This guide will walk you trough and show how you can get all the achievements in one playthrough. Releasing you from having to play the game once again for "that one" missable achievement you didn't get. If you don't want to worry about the achievements and just want to play/experience the game first, I would suggest to make a save in the beginning of every day. So when you're done with the game you can then load a specific save and do all the achievements for that day. With that out of the way lets hop right into it.

Made your best efforts to miss the funeral
Right at the beginning of the game, when your roommate informs you about the news of your grandpa Joseph Rain passing. Before walking out the room and going to the funeral, interact with (10) things around the room and the achievement will pop.

Barely resisted the urge to barbeque a bear
In your room there is a pink bear hanging around on top of your roommate's closet, click on it and Kathy says: "We meet again, Mr. Bear. Don't give me that look, it's not my fault you ended up so close to my lighter!". Naturally, you than use your zippo lighter from the inventory on the pink bear, then Kathy replies with: "Don't tempt me!". After that you will get the achievement.

Lost track of time on the road
When you exit your room, you'll be greeted with the screen of Kathy riding her motorcycle, this is the select screen for travelling between places, at this point the only option is the cemetery. Before you click on it wait a while no more then a minute, and as the achievement says enjoy the scenery until it pops.

Felt like literally taking the wheelchair for a spin
After the funeral you'll go to the Rain Residence, enter the living room where you'll be greeted by your grandma. She will ask you what took you so long to come and Kathy will reply: "Sorry, I couldn't resist taking that old wheelchair for a spin." referring to the wheelchair in the hallway. After you're done talking with her, go to the hallway and interact with the wheelchair there will be an option to ride it. Kathy will say "...It was a joke, you know." and you will get the achievement.

Felt no apparent need to let Lenny down gently
From the Rain Residence you will go to the Sheriff's Station. Talk to Lenny, that is the blond guy at the front desk when you enter the station. After you done talking to him, exit the station, he will stop you and nervously ask you out. You will get four option, all of them rejects him, but you will pick the most hurtful one: "Actually, I'd rather eat a foot." As you exit the station the achievement will appear.

Tortured an imprisoned bum
In the Sheriff's Station you will go to the double doors to the cell area and there is going to be a prisoner there. If you try to talk with him, he will respond with: "What? I can't hear you!". In order to talk to him you need to turn the small TV off. Before talking to him, turn the TV on again to get the achievement.

Rediscovered yourself as a creature of the night
After getting the evidence from the station, from the tape recorder you will hear about some research your grandpa was doing in the attic. Go back to the Rain's Residence an talk to grandma about it, she will escort you up to the attic. Unfortunately the attic light bulb if burnt out, replace it with the one form the lamp in the hallway. Turn the lights on, then off and the achievement will be yours.

Reunited with a furry friend
After you turn the lights in the attic, toward upper-left of the screen on the picture frames there is a teddy bear. Interact with it and the achievement will pop.

Became a huge fan of those sweet, addictive, not to mention cancer-inducing sticks of tobacco
After the attic part you will learn about a sixteen year old girl that drowned in 1975. To get her name you need to go to the graveyard and find her gravestone by the year of death. When you are at the graveyard you can combine the zippo lighter with the cigarettes to take a smoke, repeat this a couple of times and you will get the achievement.

Finished day one
This is a story related achievement. You will get it at the end of day one.

Engaged in flirtatious behavior on the computer
You will use Eileen's computer to process some stuff you found day 1 (overexposed picture and answering machine micro tape). Scan the micro tape and on the computer will appear a file called tape_ans_mach.wav drag it to the Voice Forge program. Select the second voice message and click the words "HELLO" and "BABY", click the button "Export to tape". Kathy will say: "How you doing?". After that the achievement will show up.

Learned a cold hard truth about your face
After processing some stuff on the computer, Eileen will come back to the room. She will sit on her bed and start doing her homework. At this point go to the mirror that is hanging of Eileen's closet and interact with it. Apart from Kathy's usual banter when you check the mirror, Eileen will add a comment about Kathy's face and it will grant us with an achievement.

Finished day two
Self explanatory and really strait forward, go trough the second day.

Amplified Goober's lung cancer
First time you go to the Clinic, there will be a man sitting in front of it. The same man that was in jail, his name is Goober. Stand close to him and light a cigar, he will start to cough. You just smoked next to a stage two lung cancer patient for an achievement, I hope you're proud.

Totally mesmerized by Goober's monologues
After talking to Goober in front of the Clinic you will learn about his film carer, you can ask him to preform a roll for the nurse in the Clinic. For this achievement you need to watch all four of his performances: The Silence of Lambert, Jacob's Bladder, The Usual Surprises, Natural Bald Killers.

Wanted to engage in a good 'ol book burning
When you enter the Church in the row of seats on the left side there is a stack of red Bibles, to get the achievement, use the lighter on them. Kathy will laugh and proclaim: "Even I wouldn't stoop that low." and after that you will get it.

Really had it out for Goober
Once you go to check on Goober in the Clinic, the nurse will say that he ran away. You can then find him in the Church sitting in the front row on the left side. Use the stun gun on him, Kathy will replay with a pun: "...Nah, that GOD old fast.". *face palm* *achievement pop*

Finished day three
Go trough the story, at the and of day three you will get the achievement.

Finished day four
Story related, can't be miss if you're planning to beat the game.

Finished the game
Self explanatory, beat the game and the achievement will be yours.

Five achievements can't be missed. You will get them as you progress trough the story, when you finish the game you are going to have all the story related achievements.

• Get on the Katmobile
  
• Wow, they're hypnotic...
  
• We've met before, haven't we?
  
• Down the rabbit hole
  
• Been there, done that

Here is the table of missable achievements and day when you can get them:


If you, the reader, notice that I missed something, made a mistake or can add more stuff to the guide that can make it better. Please write it in the comments.
If the guide helped you thumbs up, rate it so it can also help other. See you in another guide and don't forget to enjoy life!