Bailey Tipton is a student in Stuart House and is a member of the Dalton Academy Warblers. He is repeatedly mentioned to perhaps be the only "warm" Stuart student, at least towards Kurt who he very much seems to like looking after. He has openly expressed the desire to protect the relationship between Blaine and Kurt, and dislikes the trouble coming their way from Stuart House. Bailey is often seen with a pair of headphones and is clearly very interested in music. He also runs a music booth for the Valentines' Fair in E23.
As a Stuart student, he is notably close to Windsor boys and he understands that it may have estranged him just a little bit from his own House members, who feel a very fierce rivalry with Windsor House.
However, Bailey is also clearly looking after the harmony in Stuart House as it is seen that he runs around looking after people. He shows distress when the top three Stuarts Logan, Derek and Julian start to fight, and, as he has overheard the situation with Logan and Julian, he is trying to find a way to help without revealing that he knows anything.
There seems to be a hidden meaning to Bailey's attempts to protect the harmony of everyone in Stuart and Windsor, as hinted by Logan's requests for him to stop, but it has yet to be revealed by Bailey.
Bailey's character is said to have been created with real life Dalton Academy Warbler Dominic Barnes as the character mould.
All boys and some girls had a jousting competition. Everyone rode a horse, and used an eleven-foot log to try and knock off their opponents. Even Bailey went and jousted. The houses Windsor, Stuart, Hanover and Lancaster have agreed that whichever house "wins" will be served by all the other houses in a big cookout. Bailey was second to compete, and he was facing up against Cameron from Something Damaged. Bailey was worried he was going to die.
He tried to get advice from the other Stuart’s but all Milo offered was “Don’t fall off? When the flag dropped, they rode forward and Cameron’s lance struck Bailey’s chest, while Bailey’s lance collided with Cameron’s lance. Bailey was almost torn from his horse but he slumped over and held onto the reins. When Bailey was asked if he was okay to go again, he said his chest hurt and he didn’t think he couldn’t go again. He was having trouble breathing as well.
- Bailey has no pets.
- He considers himself married to music.
- In the Meta fic: Shockwave generation. Any impact he causes can be used to generate varying shockwave levels.
- He isn't crushing on anyone right now.
- He likes pets but he's no good with them.
- He can play keyboards and synthesizer, a little bass and some drums. But usually leaves that up to other people.
- If he liked someone, he'd send over a CD of love songs to test the waters.
- Everyone in Windsor loves Bailey the most from Stuart.
- He prefers apple juice to coffee, unlike everyone else in Stuart.
- His older brother is the second soloist (Joshua Tipton).
- Bailey's never been kissed.
- His parents were not at Parents Night but they sent their assistants to be there.
- His parents are diplomats who are always somewhere else in the world.
- He made a composition for the school orchestra to perform on Parents Night, he arranged what the Warblers will be singing and he's the sound guy for the night.
- When Bailey has problems writing music, he walks around aimlessly everywhere until he gets an idea.
- He’s so focused on his music that academics take a backseat until crunch time in Stuart House.
- Bailey still has Julian's tape of "Beautiful."
- Bailey made a tiny coaster when crocheting.
- When given playdoh, he shaped it into Apple headphones.
- Bailey is Dwight's age - Sophomore
- For National Brothers Week, Bailey left school to go see Joshua.
- Bailey and Riley are in the same geography class.
- Bailey likes Hershey's Kisses
- As a child, Bailey once pushed his face into a chocolate fountain because he likes chocolate.
- No matter what House it is, if Bailey is standing outside, hesitates, and paces around a bit, he has a message to bring and emissaries will be sent to get him.
- Three large boxes arrived at Stuart one day. Rory and Milo were staring at them, wondering what was going on. Logan saw the boxes then yelled out to Derek that his condom shipment for prom had arrived. Rory then looked scared so Bailey pulled him and Milo away, telling them, "Don't think about it. Pretend it's not happening, that works." Austin stood beside Milo and Rory, watching in fascination as all the condoms were taken upstairs. Bailey kept trying to coax them into pretending it wasn't happening.
- Hershey's Kisses is Bailey's favorite type of ice-cream.
- There will be a showdown of rock proportions. Haven vs. the Kings. The Kings are Dalton students. It was all Clay's idea. Clay's been going around recruiting. He's roped in Bailey, and the Windsors ganged up to make Dwight represent. Clay's still out terrorizing other houses for members. Hanover volunteered Danny and Jeff.