Thanks again jolan - entertaining set.
1. ATTERCOP - anagram "treat" + "cop" (policeman), meaning an ill-natured person. I only knew the "spider" meaning, as used by Bilbo Baggins.
2. CROSS (make the other side) WORDS (text); CROSSWORDS for our entertainment.
3. I tried something with HE and ADMAN, but could only come up with HEADWOMAN, which I don't think is right.
4. LENGTHIER - subtractive anagram of "girly chain letter" - "clarity", meaning "more long-winded"
5. Another wild guess - NABOB?