Sorry, no online dictionaries contain the exact phrase stupidly optimistic.
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Reverse dictionary results:
1. naively optimistic
 2. foolishly optimistic
3. blindly optimistic
4. fatuous
5. blimp
6. pollyanna
7. goggles
8. fond
9. dim-witted
10. dull
 11. dulled
12. bull
13. quixotic
14. anything
15. ass
16. bad
17. barren
18. bayard
19. better
20. booby
 21. bush
22. chuffed
23. come
24. dead
25. dense
26. dim
27. dimwit
28. dolt
29. dopey
30. dullard
 31. dumb
32. dumber
33. fatuity
34. foolproof
35. hat
36. inane
37. issue
38. loon
39. mensa
40. moronic

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