Here is the full list of all 31 Kitty Powers' Matchmaker achievements.
Find Big Head mode
Get through a date without spending money
Ask the waiter about all twenty dishes on the British menu
Ask the waiter about all twenty dishes on the French menu
Ask the waiter about all twenty dishes on the American menu
Ask the waiter about all twenty dishes on the Italian menu
Ask the waiter about all twenty dishes on the Chinese menu
Ask the waiter about all twenty dishes on the Jamaican menu
Ask the waiter about all twenty dishes on the Spanish menu
Ask the waiter about all twenty dishes on the Indian menu
Ask the waiter about all twenty dishes on the German menu
Ask the waiter about all twenty dishes on the Japanese menu
Ask the waiter about all twenty dishes on the Greek menu
Ask the waiter about all twenty dishes on the Swedish menu
Get walked out on 10 times
Pair off 3 Steam friends
Tap the cat 25 times
Fail every minigame in the funniest way
Ask the waiter about all the dishes on all the menus
Pair off an Edgy and a Vintage type
Pair off a Hipster and a Sporty type
Pair off a Practical and Arty type
Pair off a Chic and a Hippy type
Pair off a Glam and a Geek type
Have 50 same gender relationships
Poke characters 1000 times
Pair off Kitty Powers
Go on 100 dates
Have 50 babies
Spin the Wheel of Misfortune 4 times in one date and pair the couple off
Get all the other Achievements