My take on the kissing booth / game thing. You cannot change ages or genders, and Chrysalis is Chrysalis, not whoever you want her to be.
 
In case you suck at recognizing ponies:  
First line: Twilight Sparkle, Rainbow Dash, Pinkie Pie, Fluttershy, Applejack, Rarity.  
Second line: Princess Celestia, Princess Luna, Princess Cadance, Queen Chrysalis, Fleur-de-Lis, Trixie.  
Third line: Lyra Heartstrings, Bon Bon / Sweetie Drops, Derpy Hooves / Ditzy Doo, Colgate / Minuette, Vinyl Scratch / DJ PON-3, Octavia Melody.  
Fourth line: Aloe, Spitfire, Lotus Blossom, Lightning Dust, Cheerilee, Cup Cake / Mrs. Cake.  
Fifth line: young Granny Smith, Berry Punch, Carrot Top / Golden Harvest, Daring Do, Aunt Orange, Apple Bloom.  
Sixth line: Silver Spoon, Twist, Scootaloo, Babs Seed, Sweetie Belle, Diamond Tiara.