Lollipop Guild (5e Guild)

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April Fools!
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Lollipop Guild[edit]

We represent the Lollipop Guild
The Lollipop Guild, the Lollipop Guild.
And in the name of the Lollipop Guild
We wish to welcome you to our Land
~ Ballad of the Lollipop Guild

Small-sized males clad in all blue and carrying huge lollipops make up the infamous Lollipop Guild.

Inside the Lollipop[edit]

The Lollipop Guild is simply any male of a small-sized race that wishes to welcome people that visit their towns, cities, homes, or lands. The group has no formal leadership since all that is required of them is to sing their ballad to welcome people. Once the song is sung, they disperse and continue their business as usual. Members are typical joyful and smiling. No one feels welcomed by a scowl!

Goals of the Lollipop Guild[edit]

For all its existence, the Lollipop Guild has only ever had one mission: Greet newcomers with their song. By extension of this, the Lollipop Guild has been seen as cheerful and spreading happiness to others. Interactions with other guilds is usually minimal too and if pressed on the Lollipop Guild backs down from confrontation. They only want to bring glee and warm welcomes to others so hostility and violence is usually avoided.

Lollipop Guild Characters[edit]

Alignment: Usually neutral, often good
Suggested Races: any small-size
Suggested Classes: Bard

You might enjoy playing a Lollipop guild character if any of the following sentences describe you:

  • You enjoy welcoming others
  • You like to sing
  • You find joy in making others happy
  • You want to help others

Joining the Lollipop Guild[edit]

Membership is easy: Be short and happy! Sometimes small races can be tossed aside or looked down on and the Lollipop guild helps bring cohesion for all races that are short.
When you start adventuring, you'll find other places that have a Lollipop guild and you'll instantly be welcomed by your guildies. You may even find it fun to join in on singing with them and welcoming yourself!

Background: Lollipop Performer[edit]

Essentially a performer, you enjoy singing, dancing, and theatrical acts to welcome people. Your kind spirit makes it easy for others to get along with you and you're almost always willing to lend a helping hand. A long frown or a angry red face is nothing but an opportunity to help someone in your eyes.
Skill Proficiencies: Acrobatics, Performance
Languages: Choose one from Gnome, Halfling, or Dwarven.
Tool Proficiencies: One type of musical instrument
Equipment: Lollipop Guild attire & insignia, a musical instrument (one of your choice), a tinderbox, 10 torches, a belt pouch containing 10 gp

Feature: Smallfolk[edit]

You are recognized as an individual wanting to help others and do good. The cheerful reputation of your people proceeds you and there is no difficulty for you to find food and shelter for 1d4 nights.

Lollipop Guild Spells[edit]

Prerequisite: Spellcasting or Pact Magic class feature
For you, the spells on the Lollipop Guild Spells table are added to the spell list of your spellcasting class. (If you are a multiclass character with multiple spell lists, these spells are added to all of them.)

Suggested Characteristics[edit]


Personality Traits






Lollipop Contacts[edit]

Non-Lollipop Contacts[edit]

How Do I Fit In?[edit]


Lollipop Party[edit]


Rank and Renown[edit]


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