Sometimes words move up in the world. Their meanings change with time, becoming more positive—a process linguists call amelioration. Here are some ameliorated words that were a pinch more negative back in the day.
1. Amaze: Make crazy; confuse with terror (1200s; 1770s)
2. Amuse: Cheat, delude, or deceive (1400s)
3. Awesome: Terrifying (1670s)
4. Boy: A servant, knave, or commoner (1250s)
5. Brave: Uncivilized or savage; showy (1400s)
6. Careful: Mournful, woeful; full of anxiousness (1100s)
7. Comical: Epileptic (~1100s)
8. Cool: Calmly Audacious (1825)
9. Courage: Temper (1300s)
10. Croon: To groan or lament (1400s)
11. Dizzy: Stupid (~1100s)
12. Eager: Fierce or angry; sour, harsh, or bitter (1200s)
13. Fond: Foolish, silly (1350s)
14. Fun: Cheat, trick, or hoax (1680s)
15. Glorious: Boastful (1400s)
16. Knight: A male servant; boy (~1000s)
17. Meticulous: Fearful, timid, and full of dread (1530s)
18. Mischievous: Disastrous (1300s)
19. Nice: Stupid or ignorant; careless or clumsy (1200s)
20. Pragmatic: Meddlesome; tastelessly busy (1600s)
21. Pretty: Deceitful, tricky, or sly (~1200s)
22. Sophisticated: Unnatural; contaminated (1600s)
23. Sustainable: Bearable (1610s)
24. Ravishing: Extremely hungry (1350s)