TitleDate
#38 Engagement Fast TrackJul 10, 2018 Listen
#37 Put a Ring on ItJun 26, 2018 Listen
#36 Fast Food SexJun 19, 2018 Listen
#35 Break Up Like a ProJun 12, 2018 Listen
#34 Exes & FriendsJun 05, 2018 Listen
#33 Dirty DancingMay 30, 2018 Listen
#32 Love ClubMay 23, 2018 Listen
#31 Camp CrushesMay 15, 2018 Listen
#30 Dating EtiquetteMay 09, 2018 Listen
#29 From Matchmaker to MarriageMay 01, 2018 Listen
#28 Sucking at Dating North of the BorderApr 24, 2018 Listen
#27 Group TherapyApr 17, 2018 Listen
#26 What's Inside My Head?Apr 10, 2018 Listen
#25 More or Les with DeanApr 03, 2018 Listen
#24 Kendall & JaredMar 28, 2018 Listen
#23 Big Time DatingMar 21, 2018 Listen
#22 Ask Dean AnythingMar 13, 2018 Listen
#21 Let's Hug it OutMar 06, 2018 Listen
#20 Viall to the RescueFeb 26, 2018 Listen
#19 Dean's Friends from CampFeb 20, 2018 Listen
#18 Dating Sucks at Any AgeFeb 14, 2018 Listen
#17 Pal-entine's DayFeb 07, 2018 Listen
#16 Help! Dating SucksFeb 02, 2018 Listen
#15 Float Like a Butterfly, Bumble Like a BeeJan 24, 2018 Listen
#14 Breaking Up is Hard to DoJan 17, 2018 Listen
#13 Maybe the World Sucks at DatingJan 10, 2018 Listen
#12 Sucking at Dating Year in ReviewDec 18, 2017 Listen
#11 What Would Dean Do?Dec 12, 2017 Listen
#10 Married PeopleDec 04, 2017 Listen
#9 Deeper into DatingNov 28, 2017 Listen
#8 We All Suck At DatingNov 14, 2017 Listen
#7 Long DistanceNov 07, 2017 Listen
#6 Ghosting StoriesOct 30, 2017 Listen
#5 Signs From AboveOct 24, 2017 Listen
#4 Sext and the CityOct 17, 2017 Listen
#3 Back to the FutureOct 10, 2017 Listen
#2 Determined DeanOct 03, 2017 Listen
Episode 1Sep 26, 2017 Listen
Teaser: Dean & KristinaSep 22, 2017 Listen
Teaser: Dean Explains Why He Sucks at DatingSep 21, 2017 Listen