Sorry, no online dictionaries contain the exact phrase reassuring smile.
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Reverse dictionary results:
1. comforting
 2. encouraging
3. supportive
4. annuent
5. auspicious
6. bright side
7. countenance
8. esteem
9. favourable
10. good news
 11. heaven-sent
12. list
13. mixed blessing
14. propitious
15. respectful
16. serendipitous
17. silver lining
18. appreciant
19. commendingly
20. godsent
 21. good
22. gratefully
23. interested
24. placit
25. plausive
26. prosperous
27. regardful
28. respect
29. respected
30. respective
 31. thankfully
32. welcome
33. welcomely
34. well-found
35. whitemail
36. advantageous
37. apprecation
38. appreciatingly
39. appreciatory

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