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The fifth season of A Different World begins with the start of another school year at Hillman College, where Dwayne (Kadeem Hardison) has accepted a job as a math teacher, and Whitley (Jasmine Guy) has decided to accept Dwayne's marriage proposal and forsake a job in New York to become a campus dorm director. As Dwayne shops for Whitley's engagement ring, she searches high and low to find housing for incoming freshman Lena James (Jada Pinkett in her first series appearance). Elsewhere, Jaleesa (Dawnn Lewis) and Col. Taylor (Glynn Turman) have a surprise for everyone--almost as big as the surprise that Taylor's son Terrence (Cory Tyler) has for his dad (though Terrence's revelation has been edited from most syndication prints of this episode).