Whenever Dobie tries to get money from his tightwad father to go on dates, Herbert T. Gillis (who has the first dollar he ever earned) let's loose his signature catchphrase "OOOOO, I gotta kill that boy!" Luckily, Dobie's mother is always there to calm her husband down. When Dobie neglects his in-store chores, Herbert calls his son a "bum". A veteran, Herbert constantly reminds Dobie that "I was in the Big One – W W Two!" Herbert is also a member of the Benevolent Order of the Bison Lodge.

Winnie and Herbert T. Gillis

Other relatives in the Gillis' clan included Dobie's older brother, Davey; Dobie's cousins, Duncan "Dunky" and Virgil T. Gillis; and Herbert's brother, Tim (Duncan's father). Winnie's relatives were Wilfred, her brother; Gladys, her sister; Winnie's mother, and Winnie's other sister (who lives in Cleveland).

The first time we meet Dobie Gillis, he is meditating on a park bench with his elbow on his knee, and fist tucked under his chin. This is what Dobie had to say:

"My name is Dobie Gillis and I like girls. What am I saying? I love girls! Love 'em! beautiful, gorgeous, soft, round, creamy girls. Now, I'm not a wolf, mind you. No, you see a wolf wants lots of girls, but me? Well, I just want one. One beautiful, gorgeous, soft, round, creamy girl for my very own. That's all I want! One lousy girl! But I'll tell you a sad, hard fact. I'm never gonna get a girl. Never. Why? Because to get a girl you need money. And standing between me and money is a powerful obstacle: a POWERFUL obstacle!" [Dobies' Dad]

At Central City High School, Dobie interacts with number of interesting people. There is the teaching staff which includes Professor Leander Pomfritt, Dobie's English teacher (who calls his charges "young barbarians" and some days wishes that he'd gone into another line of business like selling air conditioners or aluminum siding; and Dr. Imogene Burkhart, the attractive Biology and Psychology instructor.

On the student body side, there is Dobie's beatnik pal, Maynard G. Krebs (who calls Dobie "Good Buddy"); Zelda Gilroy, a plain-looking, super-intelligent female (who loves Dobie - she calls him "Poopsie"); and Thalia Menninger, the beautiful but unattainable girl of Dobie’s dream. She selfishly wants to improve Dobie's status in life so she can live large with "oodles and oodles of money." Her favorite perfume was an $18 an ounce perfume called MMMM. Thalia's family included a "60-year-old father with a kidney condition, a mother who isn't getting any younger, a sister who married a loafer and a brother who is becoming a public charge."

Also in attendance at Central City High School were two spoiled rich kids. First, there was Milton Armitage (who calls Thalia "Mouse") and later Chatsworth Osborne, Jr., the heir to the Osborne National Bank fortune. His blood type was "R" (for Royal). Both Milton and Chatsworth (who called Dobie "Dobie-Do") were rivals for Thalia's affections. And while each could afford Thalia's "caviar tastes," she still kept returning to Dobie with the hopes that somehow she can make a wealthy man out of him. Unfortunately, Dobie never matches up to her high ideals.

After Thalia departed the scene, Dobie pursued Linda Sue Faversham, another stunning beauty with a similarly money-hungry disposition. Like Thalia, she needed to find someone successful to marry and "support her dismal family." Later, Linda tutored her beautiful young sister, Amanda Jean to find a rich husband, as well. Unfortunately, Dobie's cousin Duncan Gillis fell head over heels for her. But, he too, soon found out that such women were not, as his cousin Dobie explained, "meant for slobs like us."

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