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| Episode | Episode Name | Air Date | | 1 | Holy Ship! We're Sailing | Mon Feb 03, 2020 | | 2 | My Big Fat Bleak Wedding | Mon Feb 10, 2020 | | 3 | Rosé-Fueled Regrets | Mon Feb 17, 2020 | | 4 | Baby on Board | Mon Feb 24, 2020 | | 5 | Shmexual Shmension | Mon Mar 02, 2020 | | 6 | Oof! I Did It Again | Mon Mar 09, 2020 | | 7 | Oooof There It Is | Mon Mar 16, 2020 | | 8 | No Bra, No Shoes, Bad Service | Mon Mar 23, 2020 | | 9 | Parker's Big Adventure | Mon Mar 30, 2020 | | 10 | Big Deck Energy | Mon Apr 06, 2020 | | 11 | May the Breast Man Win | Mon Apr 13, 2020 | | 12 | New Chris on the Block | Mon Apr 20, 2020 | | 13 | #Awkward | Mon Apr 27, 2020 | | 14 | The Birds | Mon May 04, 2020 | | 15 | You Snooze, You Lose | Mon May 11, 2020 | | 16 | DOPE! | Mon May 18, 2020 | | 17 | Regatta Go! | Mon May 25, 2020 | | 18 | Reunion | Mon Jun 01, 2020 | | Special | Watch with Kate Chastain 110 | Mon Apr 13, 2020 | | Special | Watch with Kate Chastain 111 | Mon Apr 20, 2020 |
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