this took me an hour, but i finished the available achievements so i can share!
MADE WITH... LOVE?: choose Bob's special on the menu
PURPLE REIGN: choose purple as ur fav color
DANCING WITH THE DEVIL: See the red devil for the first time
MOST DANGEROUS GAME: say "you" when you talk about the most interesting things of the town
GREEN THUMB: choose green as ur fav color
FREE THE BEAST: let the guy in the police car go
BANG!: plan an outing with the cops
ROAM AND INVITE: ask him about other places to eat in town
HOLLY JOLLY: buy the jolly meal
SWEET TALKER: choose candy club as your favorite thing of the town when you talk to bob, and then flirt with him
RED ROBIN: choose red as your fav color
STRANGER DANGER: don't let Bob help you stand up (don't take his hand)
COPYRIGHT FREE!: buy the crabby patty meal
CODEBREAKER: write STARGAZING the first time to the stars, then STARSABOVE (i still haven't figured out the last one)
BLESSED BE: get blessed when you wake up
CINEMA SINS: chose "say something random" when bob asks what your favorite thing in the town is (the first choice/ choice that isnt "you", "candy club" or "boys N' grills)
BIG BOY BLUES: choose blue as your fav color
I CAN FIX YOU: say you don't like halloween that much
THANKS, SWEETHEART!: after you unlock the STARGAZING (codebreaker achievement) Bob will drop a piece of paper. (reccoment saving here!!!!!!!) then give it back
SNEAKY SNITCH: don't give the paper back
BURGER BUDDIES: choose "boys N' grills" when bob asks whats your favorite thing in the town
DARK DEBATE: choose black as your fav color
YELLOW SUBMARINE: choose yellow as your fav color
FOSSIL FINDER: don't let the guy out of the car, instead go inside and then be polite
CURTAIN CALL: When the lights go out in your apartment at the end of the 2nd day, look at the outlets in the dark
HIDDEN ACHIEVEMENT UNLOCKS AUTOMATICALLY!!
hope this helps! if your missing something, please ask!! <3