Sorry, no online dictionaries contain the exact phrase pickup while playing the field.

Reverse dictionary results:
1. flirtation
2. dalliance
3. casual encounter
4. hook-up
5. romance
6. coquet
7. coquetry
8. dallying
9. mug
10. stunting
11. flirt
12. prank
13. caper
14. clown
15. clown car
16. crushable
17. dandling
18. fondler
19. frolic
20. joke
21. josh
22. marlock
23. pranker
24. reveller
25. wheedle
26. wriggler
27. buller
28. circus
29. cogger
30. coquetting
31. cosher
32. crush
33. fangle
34. farce
35. fent
36. fillip
37. frolicking
38. gadder

You can look up the words in the phrase individually using these links:   pickup ?   while ?   playing ?   the ?   field ?
(A question mark next to a word above means that we couldn't find it, but clicking the word might provide spelling suggestions.)

Not helpful? You might try using the wildcards * and ? to find the word you're looking for. For example, use
pick*to search for words beginning with pick, or
*ieldto search for words ending with ield
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