12
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All of these clues are like birds of a feather. If you get them all right you'll know why they're together.

  1. Wednesday's Older Relative
  2. Woody Allen
  3. A Pigeon Holing
  4. Cholesterol Meds
  5. Cohort of Viper
  6. Someone who just wants "to look good naked!"
  7. Proctor
  8. To Persistently Annoy
  9. Cop Using 'Cuffs
  10. Termite
  11. Civil Activist
  12. NY/MN city
  13. Between 6 months and Placenta
  14. Stylin' in the 70's
  15. Almanac's Regret OR Manacle Garters

No hinting yet...

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  • 2
    $\begingroup$ 13: third trimester? 1: Uncle Lester? $\endgroup$ – Deusovi Jun 15 '16 at 2:30
  • 1
    $\begingroup$ 12: how about Rochester? $\endgroup$ – axavio Jun 15 '16 at 4:16
  • $\begingroup$ Fat fingered a downvote. Sorry. @Chowzen, can you please edit the question so I can upvote? $\endgroup$ – axavio Jun 15 '16 at 4:35
11
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Full answer:

They seem to be

Words that rhyme with "ester"

Details -

1. Wednesday's Older Relative - Uncle Fester (from Addam's Family)
2. Woody Allen - Molester (some say)
3. A Pigeon Holing - Nester sequester
4. Cholesterol Meds - Crestor (not a perfect rhyme)
5. Cohort of Viper ? Jester (from Top Gun)
6. Someone who just wants "to look good naked!" Lester (from American Beauty) per @Mike M.
7. Proctor - Tester
8. To Persistently Annoy - Pester
9. Cop Using 'Cuffs - Arrester
10. Termite - Infester
11. Civil Activist - Protester
12. NY/MN city - Rochester
13. Between 6 months and Placenta - Third Trimester per @Deusovi
14. Stylin' in the 70's - Polyester
15. Almanac's Regret OR Manacle Garters - Anagram of "Lecter's Anagram" - Miss Hester Mofet (miss the rest of me) From Silence of the Lambs. thanks to @M Oehm and @Mike M.

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