- Holden (Chad Duell) - Seen only in the episodes "International Dateline" and "Boo You!", invited Bailey to have dinner with him, but he broke up with her due to her having thrown bread rolls and butter at him after she thought that London had set up the date with him so Bailey would get "Boo You'd." He asked out Bailey in "International Dateline". However, Bailey dumped him in this episode because he threw up on her shoes when Zack gave him bad shrimp to help out Cody.
- Adonis (Adam Bay) - Bailey crushed on him when the SS Tipton docked in Greece. Adonis flirted with Bailey which made Cody jealous. In the episode "It's All Greek to Me".
- Frank - We never knew if Frank and Bailey liked each other but they did go down the water slide together in the episode " Shiponotized "
- Moose (Hutch Dano) – It is revealed in the second episode that Moose is Bailey's ex-boyfriend. He appeared on the show in "Mulch Ado About Nothing", where he tries to convince her to come back home with him since she's homesick. Bailey, however, declines as she would miss all her friends on the SS Tipton. Bailey also reminds Moose of the real reason they broke up: he always thinks that he knows what's best for her, when he really doesn't. Also in the episode "My oh Maya" Cody worries that Moose and Bailey will get back together when she goes back to Kettlecorn because a tractor fell on her Uncle Clem. Moose also appears in "Twister part 2" and " Twister part 3". Cody goes to Kettlecorn when he hears that London and Bailey are in trouble. He wants Bailey back but it turns out that Moose had come back to win her back too. In the end Bailey settles for Cody.
- Cody Martin (Cole Sprouse) – Cody begins to get a crush on Bailey because they share similar interests, therefore he pursued her endlessly, unbeknownst to Bailey (in the first season). This lasted until the first season finale "Double Crossed", when the pair form a romantic relationship. They fought and broke up two times in the season two episodes "Lost at Sea", and "Marriage 101", but got back together both times. In the episode, "Breakup in Paris", Cody and Bailey end their romantic relationship, exactly on their one year anniversary. Throughout the third season, it is widely implied that they still have feelings for each other. In the three-part episode, "Twister", Cody and Bailey get back together. In the episode "A London Carol", it is shown that Bailey and Cody will someday get married.
- Josh (Markus Silbiger) - In "So You Think You Can Date?", when Bailey lies to Cody about having a date for the 1980s/Medieval dance, she dates him in order to back up her lie and show off in front of Cody. However, London advises her to act dumb to impress him, since all the other boys were bothered by her smarts. She does so, but Josh gets annoyed by it and abandons Bailey in the middle of the dance.
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