Mondays Season 1, Episode 21: That Time When I Got Penetrated

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 min

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 min

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.

2 min

4

That Time When I Leaned In

We hear Kelly's inner dialogue as she sits in a work meeting.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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.

2 min

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 .

3 min

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.

3 min

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.

2 min

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.

2 min

18

That Time When He Didn't Like It

Kelly and Jordan get into a stupid boyfriend/girlfriend fight and argue over - well, nothing.

3 min

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.

3 min

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.

4 min

21

That Time When I Got Penetrated

Kelly visits the gynecologist, and things get awkward.

5 min

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.

3 min

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.

4 min

24

That Time When I Met Mini Me

Kelly has to explain herself to her younger self, and she's pissed.

3 min