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As would be expected from his lineage, Dean's always ready for adventure, but he and his brother are constantly hampered by their naivete and poor rearing. The work of Dr. Venture often puts the boys in danger, though they are generally unaware of how dangerous it is. Even through kidnappings, brainwashing, fondling and repeated targeting by The Monarch Dean always keeps optimistic and maintains hope of a rescue by his family's bodyguard Brock Samson, or one of Dr. Venture's inventions.
Part of his naive attitude stems from Dean's limited contact with the real world. Most of what Dean's learned about life has come either from his “learning bed” or from the skewed world of villains, violence, and super science that he is exposed to every day. Another influence is literature. As well as being a follower of The Giant Boy Detective series of books, Dean has also shown an interest in plays such as Lady Windermere's Fan, which he attempted to perform in full during the events of Fallen Arches. These interests do however cloud Dean's ability to distinguish fantasy from reality.
More recently Dean has shown a desire to live a normal life away from the dangers (and crazy stuff they have to deal with) of an adventurer (a desire once echoed by a young Rusty Venture to Dr. Jonas Venture. Due to similarities between Dean & his father, Dr. Venture appears to be grooming Dean to follow in his footsteps and carry on the family business (favoring Dean over the more rebellious Hank).