Here is the full list of all 31 Awkward achievements worth 1,000 gamerscore. It takes around 8-10 hours to unlock all of the achievements on Xbox One.
Play your first game
Played a team game
Play a solo game
Play a duo game as friends
Play a game with 6 players
Play a game where everyone enters a name
Get your first awkward moment
Get your first match in a solo game
Get three matches in a row in a duo or team game
Get three awkward moments in a row in a duo or team game
Correctly match an answer in under 2 seconds
Correctly match every question during a double points round
Get the final awkward question right
Get the final awkward question wrong
Have a rematch
Finish a duo game on 100% matchability
Finish a duo game on under 20% matchability
Finish a duo game on 0% matchability
Finish a team game with all team scores tied
Finish a solo game with 80% or higher conformity
Finish solo game with under 20% conformity rating
Someone scores over 80% familiarity in a multiplayer match-up game
Someone scores 100% familiarity in a multiplayer match-up game
Someone scores 0% familiarity in a multiplayer match-up game
Play a duo game as friends and finish with over 80% matchability
Finish a game with an average answer speed of under 3 seconds
Correctly match 100 answers in solo games
Complete 10 games
Face 1000 questions
Play on a Saturday night
Play on Valentine's day