#3713176 - safe, artist:baron engel, derpibooru import, derpy hooves, trouble shoes, earth pony, pegasus, pony, semi-anthro, g4, belly, belly button, female, flower, image, jpeg, male, mare, monochrome, pencil drawing, ship:derpyshoes, shipping, simple background, spread wings, stallion, straight, traditional art, wings

Derpibooru

Uploaded 01:16, February 17, 2026 by Anonymous #6D71

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Size: 1400x1094 | Tagged: safe, artist:baron engel, derpibooru import, derpy hooves, trouble shoes, earth pony, pegasus, pony, semi-anthro, g4, belly, belly button, female, flower, image, jpeg, male, mare, monochrome, pencil drawing, ship:derpyshoes, shipping, simple background, spread wings, stallion, straight, traditional art, wings

Description:

One of the drawings from my recent Friday the 13th themed Picarto stream. The next day was Valentine's Day, but if there's anypony who embodies bad luck it's old Trouble Shoes, and if there's another pony who's sometimes been cursed with bad luck it's Derpy Hooves.

But maybe fate will just leave these two alone for at least one day. Yes I usually imagine Derpy with Doctor Whooves. However I am willing to make exceptions.

Hang on a sec...
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I am not a robot!

Main Species Shorthands A B Season 9 8 7 6 5 4 3 2 1

Episode Spoilers
spoiler:s09e20
spoiler:s09e21
spoiler:s09e22
spoiler:s09e23
spoiler:s09e24
spoiler:s09e25
spoiler:s09e26

General Spoilers
spoiler:eqg specials
spoiler:comic
spoiler:eqg series (season 2)
spoiler:s09
spoiler:rainbow roadtrip
spoilers for another series

Species
anthro
equestria girls
human
humanized
pony
earth pony
pegasus
unicorn
alicorn

Often Forgotten
solo
screencap
image macro
monochrome
oc
photo
Tag original characters oc:name

Major
bat pony
changeling
changedling
deer
dragon
griffon
classical hippogriff
yak
zebra

Minor
abyssinian
breezie
centaur
diamond dog
draconequus
kirin
seapony (g4)
siren
sphinx

Animal
chimera
cockatrice
hydra
manticore
parasprite
phoenix
tatzlwurm
timber wolf
windigo

Misc
original species
hybrid

Mane Cast
m6 - mane six
pt - princess twilight
ts - twilight sparkle
rd - rainbow dash
ry - rarity
aj - applejack
fs - fluttershy
pp - pinkie pie
sp - spike

Secondary Cast
cmc - cutie mark crusaders
ab - apple bloom
sl - scootaloo
sb - sweetie belle
tia - princess celestia
luna - princess luna
pcd - princess cadance
sa - shining armor
sg - starlight glimmer

More Ponies
tx - trixie
sus - sunset shimmer
sombra - king sombra
qc - queen chrysalis
dc - discord
nmm - nightmare moon
sf - spitfire
sn - soarin'
ld - lightning dust

More Apples
bm - big macintosh
gs - granny smith
bb - braeburn
bs - babs seed

Fillies and Colts
ss - silver spoon
dt - diamond tiara
pfh - princess flurry heart

Background Ponies
dh - derpy hooves
dw - doctor whooves
cgt - colgate
bon - bon bon
oct - octavia melody
dj - vinyl scratch
bp - berry punch
pbb - prince blueblood

Uncategorized
maud - maud pie
coco - coco pommel
suri - suri polomare
rg - royal guard
za - zecora
mm - mayor mare
pdp - pinkamena diane pie
owol - owlowiscious
opal - opalescence

Other Things
cm - cutie mark
eoh - elements of harmony
nmn - nightmare night

1-2. the beginning of the end
3. uprooted
4. twilight's seven
5. the point of no return
6. common ground
7. she's all yak
8. frenemies (episode)
9. sweet and smoky
10. going to seed
11. student counsel

12. the last crusade (episode)
13. between dark and dawn
14. that's a laugh
15. 2 4 6 greaaat
16. a trivial pursuit
17. the summer sun setback
18. she talks to angel
19. dragon dropped
20. a horse shoe-in
21. daring doubt

22. growing up is hard to do
23. the big mac question
24-25. the ending of the end
26. the last problem

1-2. school daze
3. the maud couple
4. fake it 'til you make it
5. grannies gone wild
6. surf and/or turf
7. horse play
8. the parent map
9. non-compete clause
10. the break up breakdown
11. molt down

12. marks for effort
13. the mean 6
14. a matter of principals
15. the hearth's warming club
16. friendship university
17. the end in friend
18. yakity-sax
19. on the road to friendship
20. the washouts (episode)
21. a rockhoof and a hard place

22. what lies beneath
23. sounds of silence
24. father knows beast
25-26. school raze
Special. best gift ever

1. celestial advice
2. all bottled up
3. a flurry of emotions
4. rock solid friendship
5. fluttershy leans in
6. forever filly
7. parental glideance
8. hard to say anything
9. honest apple
10. a royal problem

11. not asking for trouble
12. discordant harmony
13. the perfect pear
14. fame and misfortune
15. triple threat
16. campfire tales
17. to change a changeling
18. daring done?
19. it isn't the mane thing about you
20. a health of information

21. marks and recreation
22. once upon a zeppelin
23. secrets and pies
24. uncommon bond
25-26. shadow play

1-2. the crystalling
3. the gift of the maud pie
4. on your marks
5. gauntlet of fire
6. no second prances
7. newbie dash
8. a hearth's warming tail
9. the saddle row review
10. applejack's "day" off
11. flutter brutter

12. spice up your life
13. stranger than fan fiction
14. the cart before the ponies
15. 28 pranks later
16. the times they are a changeling
17. dungeons and discords
18. buckball season
19. the fault in our cutie marks
20. viva las pegasus
21. every little thing she does

22. ppov
23. where the apple lies
24. top bolt
25-26. to where and back again

1-2. the cutie map
3. castle sweet castle
4. bloom and gloom
5. tanks for the memories
6. appleoosa's most wanted
7. make new friends but keep discord
8. the lost treasure of griffonstone
9. slice of life (episode)
10. princess spike
11. party pooped

12. amending fences
13. do princesses dream of magic sheep
14. canterlot boutique
15. rarity investigates
16. made in manehattan
17. brotherhooves social
18. crusaders of the lost mark
19. the one where pinkie pie knows
20. hearthbreakers
21. scare master

22. what about discord?
23. the hooffields and mccolts
24. the mane attraction
25-26. the cutie remark

1-2. princess twilight sparkle (episode)
3. castle mane-ia
4. daring don't
5. flight to the finish
6. power ponies
7. bats!
8. rarity takes manehattan
9. pinkie apple pie
10. rainbow falls
11. three's a crowd

12. pinkie pride
13. simple ways
14. filli vanilli
15. twilight time
16. it ain't easy being breezies
17. somepony to watch over me
18. maud pie (episode)
19. for whom the sweetie belle toils
20. leap of faith
21. testing testing 1-2-3

22. trade ya
23. inspiration manifestation
24. equestria games
25-26. twilight's kingdom

1-2. the crystal empire
3. too many pinkie pies
4. one bad apple
5. magic duel
6. sleepless in ponyville
7. wonderbolts academy
8. just for sidekicks
9. apple family reunion
10. spike at your service
11. keep calm and flutter on

12. games ponies play
13. magical mystery cure

1-2. the return of harmony
3. lesson zero
4. luna eclipsed
5. sisterhooves social
6. the cutie pox
7. may the best pet win
8. the mysterious mare do well
9. sweet and elite
10. secret of my excess
11. family appreciation day

12. baby cakes
13. hearth's warming eve (episode)
14. the last roundup
15. the super speedy cider squeezy 6000
16. read it and weep
17. hearts and hooves day (episode)
18. a friend in deed
19. putting your hoof down
20. it's about time
21. dragon quest

22. hurricane fluttershy
23. ponyville confidential
24. mmmystery on the friendship express
25-26. a canterlot wedding

1-2. friendship is magic
3. the ticket master
4. applebuck season
5. griffon the brush off
6. boast busters
7. dragonshy
8. look before you sleep
9. bridle gossip
10. swarm of the century
11. winter wrap up

12. call of the cutie
13. fall weather friends
14. suited for success
15. feeling pinkie keen
16. sonic rainboom (episode)
17. stare master
18. the show stoppers
19. a dog and pony show
20. green isn't your color
21. over a barrel

22. a bird in the hoof
23. the cutie mark chronicles
24. owl's well that ends well
25. party of one
26. the best night ever

Tags:

I am not a robot!

Sources:

https://www.deviantart.com/baron-engel/art/The-First-Date-1299789380

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