The words in each set have a common connection, something that bonds all three of them in some way.
For example: The connection for "Penny-Zachary-Will" is
TV characters from Lost in Spacex 1. CLIPPER - SLOOP - CATAMARAN
x 2. ENIAC - UNIVAC I - MAC HACK VI
x 3. A SATELLITE - A MIRROR - A REMINISCENT PERSON
x 4. THING - LURCH - COUSIN ITT
x 5. KIX - TRIX - CHEERIOS
x 6. JANE SEYMOUR - CATHERINE HOWARD - ANNE BOLEYN
x 7. DAVID LETTERMAN - ALFRED E. NEWMAN - LAUREN HUTTON
x 8. THE BIG SLEEP - THE PETRIFIED FOREST - THE MALTESE FALCON
x 9. DOOMSDAY - STEEL CURTAIN - PURPLE PEOPLE EATERS
x 10. LAVA - COAST - IVORY