Achievements count - 21
Playthroughs to 100% - 4-5
Time to 100% - 1.5-2h

Read this guide first to find out what different characters like for romance achievements.
https://ad.gamersky.info/@steamcommunity.com/sharedfiles/filedetails/?id=1874236768

Go to preferences:
Set Skip: Unseen text, After choices, Transitions


Choose kind options when it is available (heart icon) for romancing Juniper.

Start the game.
Press Done editing.
Yes, that's correct.
Give the weird little app a shot.
Yes, absolutely!
Sure, give me the sales pitch.
Any.
I'd like to use the identity indicators.
Save 1 (Romance/no romance achievements)
Sure, i'm open to the possibility.
Get dressed

Other choices for different romance routes depend on personalities. Choose someone from the list (Gavin, Naomi, Ashley, Percy, Queen Bee, Theo, Juniper) to romance in current playthrough. Interact with him/her when its possible and choose romance options. Chooose options they like from guide with personalities to increase chances. Other choices are irrelevant, but some of them leads to early ending with no achievement.

01: Put Your Quarter Up
Clear Level 01.


It's okay. I'm here I want to be. (During talk with Juniper)

Save 2 here

Choose any, skip until you get achievement. Load 2, repeat 2 more times.
Better Dead Than Red
Obtain Zombie Meltdown.


Let's Typing
Obtain Phrase Invaders.


Use the Magic Sword
Obtain Wyvern Keep.


Continue skipping.
02: Chasing Ghosts
Clear Level 02.


I can smile through this. (During talk with Juniper)
Accept default name with Enter, then choose That works!
Fantastic! (During talk with Juniper)
Its hardly a doodle. You did a great work designing it.

03: Take it to the MAX
Clear Level 03.


Follow your dreams, Jupiter. Be independent.
04: Player Versus Player
Clear Level 04.


Jupiter's talking with Iris.
It feels great to be back. Like coming home.
Tell Juniper the truth.
Save 3 (Main choice for romance achievement, which you gonna get on level 8)
Jupiter
4 choices with heart, then "Cartoons...", The stealth option, I'm always be here for you.

05: Under the Boardwalk
Clear Level 05.


Save 4 before "I want a new job."

I want a new job.
Yes. It's time to grow up.
The Good End
Abandon your dreams.


Load 4
I want my dream back.

06: Hit the Lever
Clear Level 06.


You are not much better at tossing (During talk with Juniper)
Why didn't you tell me this before

Things are definitely different as a couple than as roomies...

07: New Game Plus
Clear Level 07.


Level 8:
Choose kind options with heart.
A sneaky ninja? (During talk with Juniper)
Continue choosing any kind options with heart.
More Than BFFs
Romance Juniper.


08: Kill Screen
Clear Level 08.


Load 3 and try other characters on your own. If they refuses to romance with you on this point, start a new game and treat them better (Choose dialogue options with icons they like and spend as much time as possible with them).

Breaking the Meta
Romance QueenBee.


Cosplay Connection
Romance Ashley.


Double Dance
Romance Teo.


Extra Life
Romance Percy.


Pixel Heart
Romance Percy.


Reasonable Romance
Romance Gavin.


Love in a Time of Quarters
Romance everyone.


Continue skipping after getting last Romance someone achievement until you get this one.

Load 1
Choose "I'm just not interested in romance Iris", "Yes. I'm not interested in romance" in Level 1. then finish game. Save frequently after Level 5 as some choices leads to early ending. Choose dialogues with space invader icon (white) and scales (blue). You will get The Power of Friendship somewhere in Level 8.
The Power of Friendship
Don't romance anyone.