Sorry, no online dictionaries contain the exact phrase smiling sadly.
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Reverse dictionary results:
1. wistful
2. melancholic
3. rueful
4. bittersweet
5. brutally
6. carefully
7. dementedly
8. dolefully
9. drearily
10. gravamen
11. grievous
12. heavy-hearted
13. heavy heart
14. maudlinly
15. melancholious
16. melancholy
17. mesto
18. passion
19. poignant
20. site
21. acherontic
22. baleful
23. balefully
24. broken-hearted
25. broken heart
26. broken hearted
27. calamitously
28. catastrophically
29. caustically
30. devastatingly
31. direfully
32. direly
33. doleful
34. dolefull
35. dolent
36. dolour
37. dystopian
38. elegiacal

You can look up the words in the phrase individually using these links:   smiling ?   sadly ?
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Not helpful? You might try using the wildcards * and ? to find the word you're looking for. For example, use
smil*to search for words beginning with smil, or
*adlyto search for words ending with adly
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