This achievement is one of about 4 that require luck to get. Everytime you play Rock Paper Scissors there is a 1 in 4 chance of getting this achievement. Luckily the Rock Paper Scissors choice comes early in the game.

Latest version has a trick: If you back up to where you choose “Play Rock Paper Scissors” it will randomly pick again.

Doing the Sex on the Couch walkthrough will get you this one.

Doing the Shopping Spree walkthrough will get you this one.

It basically involves going to the store, buying beer and drinking it all. You must go to the park or downtown before you can go to the store.

This achievement is one of about 4 that require luck to get. It is the lone achievement playing the board game Pachisi, which the Things to Do With Friends walkthrough gets to. Every time you roll the dice there is a 1 in 6 chance of getting this achievement. Most games of Pachisi require a few rolls to win/lose.

You can cheat and go back before you rolled and get a different outcome. This only works on the latest version.

You have to dance with Ariane 7 times to achieve this one. The obstacle here is that Ariane limits dancing to the stereo at home to 6 times. Every time you change the music counts as a dance.

So the way to get to 7 is to dance at home until she won’t anymore, then go downtown and dance at the nightclub which she will do even though she is done dancing at home.

Note the other way around does not work. Dancing downtown counts against the limit at home, so you must go downtown after exhausting the dancing at home.

It is possible to get 8 dances in a date if you go get Rebecca as Ariane will dance twice at the club, once with you and once with Rebecca and they both count.

Getting this achievement involves the dress variation of The Rebecca Trilogy 3 – Rebecca Stays The Night, and Ruins It

We need to swim first before meeting Rebecca, So start with Backyard Picnic this time:

Have a drink
Go inside
Get dressed and go for a drive
Wait for her in the hallway
Get in the drivers seat
Go downtown
Lingerie Store

Get past the lingerie puzzle, see The Rebecca Trilogy 1 – Marco Polo for how. Then we see Rebecca:

Agree to drinks at the club with Ariane and Rebecca
Buy the next round of drinks
Let them continue to dance (this leads to drinks at Ariane's)

Follow Rebecca
No, it wouldn’t be too presumptuous
Strip naked and join Rebecca in bed

This is a slight variation on Sex on the Couch

Begin first by following Pizza Dinner or Steak Dinner as they get you to the same place. From there its a short play for sex:

Dance in the living room
(any music)
Change music
Go somewhere else
Go to the living room
Kiss her (to open up the couch make out scene)
Grab her breasts
Ask her to take her shirt off
Kiss her tits
Rub her thighs
Ask her to take her pants off
Ask her to take her panties off
Massage her butt
Massage her back
Ask to do it again (this will end the date and get the achievement)

Drink Absinthe. Doing the Pool Hijinx walkthrough will get you there.

Another variation of Sex on the Couch will get you there:

Begin first by following Pizza Dinner or Steak Dinner as they get you to the same place. From there its a short play for sex:

Dance in the living room
(any music)
Change music
Go somewhere else
Go to the living room
Kiss her (to open up the couch make out scene)
Grab her breasts
Ask her to take her shirt off
Kiss her tits
Rub her thighs
Ask her to take her pants off
Ask her to take her panties off
Touch her pussy (this is different)
Ask for oral sex (Ariane will refuse)

This achievement is one of about 4 that require luck to get.

Once you are done eating (any meal) and before you go swimming or hot tubbing, go to the kitchen for dessert and play “spin the bottle”. If it lands on Park Photoshoot you get the achievement.

You need to do this at least once while still dressed casually to reach the bikini photoshoot. Save your game before the photoshoot begins because there are two versions of the bikini photoshoot and you need them both for the shutterbug achievement.

If you do the Konami code, the bottle will always land on park photoshoot, however you cannot get achievements in cheat code mode.

A variation on the Striptease at Home walkthrough.
Begin first by following Pizza Dinner or Steak Dinner.

Go to the living room
Massage her shoulders
Go somewhere else
Go to the bedroom and put on a swimsuit
Wait in the hallway
Have a drink
Go inside
Dance in the living room
Pick a rock playlist
Change music
Pick a country playlist (Ariane will take off her top)
Change music
Pick a rock playlist 
(Ariane will take off her bottoms, achievement unlocked)

Doing the Shopping Spree walkthrough should get you there.

This is an achievement you can get before dinner, but it results in the date ending quickly.

Say something funny
Kiss her
I just wanted to test if our saliva was compatible.
Turn on some music
Pick a romantic playlist
Kiss her while dancing
Dip and kiss her neck
Go somewhere else
Let’s go to the backyard
Change into a swimsuit
Follow her into the bedroom

The date immediately ends, but you got the achievement.

This one is unlocked by playing with Ariane’s breast too much. You can start off with Sex on the Couch but then focus on her breasts until she gives up.

Begin first by following Steak Dinner then:

Dance in the living room
(any music)
Change music
Go somewhere else
Go to the living room
Kiss her (to open up the couch make out scene)
Grab her breasts
Ask her to take her shirt off
Kiss her tits
Grab her breasts
Kiss her tits