Dipsy the Wooper was the third Pokémon that Radic found in Johto. Dipsy, like Chirin, joined with Radic voluntarily, flopping up onto his boat while he was fishing and then deciding to come with him without a battle.

Dipsy was small for a Wooper, and is still very small for a Quagsire. In fact, he's about the size of a Wooper AS a Quagsire, and this is something that frustrates him greatly. Not only that, but he seems to be shrinking with time. As a result, he's very sensitive about his size and does NOT appreciate any comments about it.

Dipsy is also one of Radic's smartest Pokémon. Part of why he decided to go with Radic in the first place was because he was fascinated by the concept of Ownership as it related to Pokémon, what that meant to him, and something about Radic interested him enough to give it a try. Dipsy loves reading books, watching TV, doing anything that engage his mind, and he loves discussing things he's interested in with anyone who will listen. He considers himself something of a scientist, and prides himself on his conclusions being based on evidence and logic. Because of his thirst for knowledge, Dipsy has a fairly extensive knowledge of different Pokémon and their types, thanks to hours spent with Radic's Pokédex. He's also very familiar with type matchups and various moves, and he would often help Radic with strategies or advice if Poe or Chopan couldn't let Radic see.

Due to most Quagsire being rather unintelligent, most people tend to underestimate Dipsy or not take his advice seriously. This bothers him to no end.

Dipsy is also nearsighted, and has been since he was a Wooper. As a result, Radic went and got some glasses made for him, and every few years or so the prescription has to be strengthened. Without his glasses, Dipsy has a hard time of doing anything.

Dipsy tends to be aloof, although it's not intentional, and while he tries to be friendly, he can often be condescending and rude without intending to be. Dim Pokémon tend to make him somewhat uncomfortable (for example, Accident), as well as Pokémon that don't communicate in a normal way like Rezna. He gets along well enough with Chirin and Fauntleroy, although Poe and him disliked each other from the start. Chopan rubs him the wrong way, which is no surprise at all, although he's okay enough with Mozart.

Generally, Dipsy tries to be sociable enough, although he's not the best at it. He tries to be polite and patient when he can. He listens to Radic most of the time, except when he thinks a different strategy would work better, and generally doesn't cause Radic as many problems as some of his other Pokémon. In Johto, he had Surf, Earthquake, Amnesia, and Slam.

Dipsy is in fics where Radic's later Pokémon come into play, mostly Together Forever.