It Takes Two

 

 

The answers to the clue phrases are in alphabetical order:

• Dissuade the fleet she owns (5 3 6) - DETER HER ARMADA
• Self-absorbed person put a disguise on the face of a young nocturnal bird (7 6 5) - EGOTIST MASKED OWLET
• It's read when a dumbwaiter dies (8 6) - ELEVATOR EULOGY
• Newly-created kilt gives off energy (5 5 8) - FRESH SKIRT RADIATES
• "Pastry made of a secreting organ, m'lord?" ("5 4, 3?") - "GLAND TART, SIR?"
• Wonderful green gem (5 7) - GREAT EMERALD
• "___, will travel (to fruity green proms or movie premieres)" (4 4 4) - HAVE LIME LIMO
• Non-extremists fire a weapon at a branchlet (9 5 4) - MODERATES SHOOT TWIG
• Challenge issued to a raised landform that doesn't keep still (6 4 4) - MOVING HILL DARE
• Currently smashed into pieces (3 9) - NOW SHATTERED
• Indian mystics that are sleazier (or more viscous) than any others (8 6) - SLIMIEST FAKIRS
• Debonair sweepstakes that occurs once every seven days (5 6 5) - SUAVE WEEKLY LOTTO

The flavortext and coloring of the grid suggest NECCO Sweethearts Conversation Hearts. (NECCO's factory was located on Mass Ave from 1927 to 2003.) Most of the clue phrases each lead to an anagram of two phrases found on Conversation Hearts. Two lead to an anagram of a heart phrase and either START or END.

Every heart phrase used is used twice, allowing the anagrams to be chained together:

• "GLAND TART, SIR?" = START + DARLING
• MOVING HILL DARE = DARLING + LOVE HIM
• HAVE LIME LIMO = LOVE HIM + EMAIL
• SLIMIEST FAKIRS = EMAIL + FIRST KISS
• FRESH SKIRT RADIATES = FIRST KISS + DEAR HEART
• DETER HER ARMADA = DEAR HEART + DREAM
• GREAT EMERALD = DREAM + GET REAL
• ELEVATOR EULOGY = GET REAL + LOVE YOU
• SUAVE WEEKLY LOTTO = LOVE YOU + SWEET TALK
• EGOTIST MASKED OWLET = SWEET TALK + GOOD TIMES
• MODERATES SHOOT TWIG = GOOD TIMES + TWO HEARTS
• NOW SHATTERED = TWO HEARTS + END

Entering the heart phrases in the appropriate order allows the word LEATHERETTE to be read down the "hearts" (center letters) of the phrases.