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First one seems much the same as her normal ’do. second is cute-and-innocent, while third is hnng. Fourth looks great, reminds me of Princess Marle, and the fifth one looks like she had some fun last night.
Software Patch - For supporting the site
Commission Junkie - Derpi Supporter
Air Ponyville -
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Roseluck - Had their OC in the 2023 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Verified Pegasus - Show us your gorgeous wings!

The courage to jump...
#3 reminds me of Akane from Ranma 1/2, before her haircut.
Also my phone spell checker recognizes both “Akane” and “Ranma”. Hu
Derpy! - For Patreon supporters
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -
Preenhub - We all know what you were up to this evening~
My Little Pony - 1992 Edition
Silver Bit -
Ruby -
Wallet After Summer Sale -

Planeswalker — FoME
“The butterfly stays.”  
“But darling, there are so many other possibilities if I could just—”  
The butterfly stays.”  
“Well, the customer’s always right!”