Broadcast date
05-06-2017 • 24 episodes
Episodes of this season
1. That Time When I Got Circumcised
Kelly drives with her boyfriend, Jordan, and gets an unexpected call from Mom that she takes on speaker phone.
2. That Time When I Started Adulting
Kelly sits down with her boss to discuss her new job, but things get awkward when she realizes her boss has no idea that she's been hired.
3. That Time When Once A Week Wasn't Enough
Kelly is caught off guard when she runs into her friend, Elle, and she jumps into a sex talk.
4. That Time When I Leaned In
5. That Time When My Vagina Fell Off
Kelly has a bizarre, quirky dream. Her boyfriend tries to help her from the other side of the door. Things get awkward when he finds out what the strange problem is their dealing with.
6. That Time When Kyle Gave Me The Creeps
Kelly walks in on her co-worker, Creepy Kyle, while he's Facebook stalking her. We hear Kelly's thoughts as she tries to leave this awkward situation.
7. That Time When Sugar Wasn't So Sweet
Kelly gets a Brazilian wax, but instead of a traditional wax, she opts for 'sugaring'. She's surprised when she finds out her regular esthetician is out, and Marsha will be waxing her instead. We hear Kelly's thoughts as she tries to get through this awkward situation.
8. That Time When Mom Gave Me A Sex Talk
There's nothing like having an awkward sex talk with your parents - In this episode, Kelly is at work when she receives an unexpected call from Mom. The conversation becomes awkward when Mom asks Kelly about her sex life.
9. That Time When I Was On Display Part 1
What if millennials were on an episode of a Nat Geo documentary — like an animal in the wild — and there was a tour guide narrating their experiences. In this episode, Kelly is in yoga when a tour guide and group walk in as if they’re on a safari or Disneyland tour. They re-appear and follow her throughout her daily life.
10. That Time When I Discovered the True Meaning of Anal
Kelly meets Anal Annie, and she trains her on how to work at the front desk in their office.
11. That Time When I Had A UTI
Kelly has a UTI, and her friend, Kate, gives her advice as they get drinks. Kate gives her unconventional advice when she tells her how to cure UTIs naturally by sticking a clove of garlic up her vagina.
12. That Time When I Was On Display Part 2
What if millennials were on an episode of a Nat Geo documentary — like an animal in the wild — and there was a tour guide narrating their experiences. In this episode, the Tour Guide and tour group return while Kelly is hooking up with her boyfriend, Jordan.
13. That Time When I Was In Shipping
Kelly's co-worker, Jeremy, tells her that he has a great work opportunity for her that he thinks will be a good experience. Kelly is surprised when she finds out that opportunity is cleaning the storage room in the basement.
14. That Time When It Was Game Time
We hear Kelly's thoughts as she tries to watch an Arsenal soccer game with her boyfriend, Jordan .
15. That Time When My Chakras Aligned
Kelly goes to a party with her friend in Los Angeles, and she ends up getting stuck in a conversation with a guru, George.
16. That Time When I Didn't See Kyle Coming
Kelly runs into Creepy Kyle, and the conversation becomes awkward when he checks out Kelly's chest/band shirt.
17. That Time When I Called During Days
Kelly calls Dad and Mom on her lunch break to get advice, and the conversation doesn't go as planned.
18. That Time When He Didn't Like It
Kelly and Jordan get into a stupid boyfriend/girlfriend fight and argue over - well, nothing.
19. That Time When Life Was Falling Apart
Kelly is caught off guard when she runs into her friend, Elle, and she jumps into a rant about her first world problems.
20. That Time When I Had a Scare
Kelly gets a call from the Scream Voice, while she's watching Girls. Instead of asking her if she likes scary movies, he asks her if she likes babies. Kelly then finds herself in horror movie scenes from Scream, The Ring, and I Know What You Did Last Summer, but with a MONDAYS twist.
21. That Time When I Got Penetrated
22. That Time When I Got Life Coached
Kelly doesn't know what to do with her life and seeks advice from a life coach.
23. That Time When I Met My Future Self
Kelly suddenly appears in a white space and thinks she's dead, but she's actually meeting with her future self.
24. That Time When I Met Mini Me
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This season's cast
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