| 281 | Dr. Swati Mohan 2021-02-27 |
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| 282 | Best of WWDTM February 2020 2021-02-20 |
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| 283 | Abby Phillip 2021-02-13 |
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| 284 | Owen Wilson 2021-02-06 |
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| 285 | Jen Psaki 2021-01-30 |
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| 286 | Mandy Patinkin and Kathryn Grody 2021-01-23 |
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| 287 | Phoebe Bridgers 2021-01-16 |
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| 288 | Jane Krakowski 2021-01-09 |
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| 289 | WWDTM New Year 2021 2021-01-02 |
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| 290 | WWDTM Christmas 2020 2020-12-26 |
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