This Is Awkward

Awkward Episodes

62| My Girlfriend's Adult Kids Won't Pay for Anything!

What do you do when your partner's adult children constantly expect you to pay the bill? Join us as we dive into the struggles of dating as our anonymous writer tells us about the added stress of dealing with his partner's entitled adult children....

61| My Cousin is Trying to Make Me Buy a House

What do you do when a family member won't stop pressuring you to buy a house? This episode we're tackling a situation that many of us have probably faced at some point - unsolicited financial advice from family. A listener is trying to decide whether...

Patreon Preview: That Thong Th-Thong Thong Thong

Here's another preview of our Patreon Only content as a special New Year gift! Hear how big of an impact the Thong Song had on Allison's life and that time she assaulted Joey Fatone.   Join Us On Patreon Get access to even more bonus content with...

Patreon Bonus: Caroling Gone Wrong

Here's a preview of our Patreon Only content as a special Christmas gift! Join Us On Patreon Get access to even more bonus content with our This Is Awkward Patreon starting at just $3!   Have an awkward money situation? If so, we want to hear...

60| Middle School Bullies

Did you ever wear a knock off clothing brand to school? Today’s call comes in from one of our Patrons who got viciously made fun of after another student caught a typo on their shirt. We'll discuss how to help your kids navigate these types of...

59| Are My In-Laws Stealing From Me?

What would you do if you found out that you've been paying hundreds of dollars more for your phone bill that you should? Our anonymous writer discovered that he and his wife have been over paying their share of their in-laws phone plan for years. Our...

58| My Sister in Law Somehow Always Forgets Her Wallet

What do you do when your sister in law thinks that you should pay for every meal? This week we discuss a woman who is fed up with her sister in law who somehow always "forgets" her wallet every time they go out to eat. She's reached her breaking point...

57| My Mom Gives Gifts Like the Grinch

What do you do when your mom hates giving gifts but does it anyway, but with strings attached? That's what today's episode is all about. A listener wrote in wanting to know how do they handle a mom who makes a big deal about how much they pay for...

56| My Neighbor is Flooding My Basement

My neighbor flooded my basement. It was an accident, but it still happened. A listener wrote in needing to face this situation head on, but they don’t know how to approach their neighbor. How should she bring up the conversation without ruining a...

55| My Friend's Wedding is Going to Bankrupt Me!

A listener is starting to get overwhelmed by the growing cost of their friend’s wedding. Between gifts, clothes, flights, and hotels, it’s all adding up. Should they approach their friend about this or just keep quiet and spend the extra money?...

54| How Do I Help My Parents Without Feeling Resentful?

How do I talk with my parents about their financial struggles and find a way to help them without feeling resentful? That's the question we received this week from a listener.   Join Us On Patreon Get access to even more bonus content with our...

53| Is My Mother In Law Trying to Rip Us Off?

Grandma wants to babysit, but at a pretty price. A listener writes in feeling like she’s being taken advantage of by her mother in law and her high rates. How should she approach this conversation and figure out what is a fair price?   Join Us...

52| How Do I Say No to My In-Laws?

Navigating money conversations with your parents or in laws can be very awkward!   In this episode we hear from one of our listeners who is confronted with the reality that she and her partner will likely be supporting her in laws financially...

Careers & Money

51| I Haven't Gotten a Raise in 3 Years! What Do I Do?

A listener wrote in because they haven’t had a raise in the past 3 years. They feel undervalued and with inflation on the rise, they are seeing the effects on their budget. Should they approach their boss, and  if so, what’s the best way to...

Relationship Problems

50| Should I Reimburse My Ex?

What happens when you and your partner separate but you both put money in to your home? We hear from a listener who received an invoice from her ex for a few home upgrades that he made to her home. Should she pay them or should she refuse? This Is...

Awkward Friend Issues

49| My Friend Thinks I’m A Bank

In today’s episode, hear from someone who has given money to a friend in the past. Lately, this friend has started expecting this type of gift money more and more. The caller says they are starting to feel like a bank. What should they do?  ...

Relationship Problems

48| Should We Open A Joint Bank Account?

We hear from someone who had a negative experience with a previous partner. This experience has forced them to wonder when she should combine finances with a partner and how money should be split.   Join Us On Patreon Get access to even more...

Relationship Problems

47| I Can't Keep Supporting My Partner

In today’s episode, discuss an awkward situation between two partners who are living together. One is constantly asking the other for money and the other partner has had it. How should they approach this situation in a respectful way?   Join Us...

Relationship Problems

Awkward Revisit: My Husband is Sharing Way Too Much!

Today's anonymous writer is dealing with a husband who is a little too open with his parents about their finances. Join Our Patreon Get access to even more bonus content with our This Is Awkward Patreon!      Have an awkward money...

Awkward Friend Issues

46| Do You Plan to Pay Me Back?

In today’s episode, we hear from someone who wants to know whether or not she should confront her friend who never pays people on time. The caller sees it as disrespectful and wants to know if she would be out of line to bring this money habit up to...

Awkward Friend Issues

45| How Are You Paying For This?!

In today’s episode, we discuss a situation where someone finds out that their partner has a hidden credit card…and has for the past 12 years of their marriage. He’s angry and questions whether or not his feelings are justified.   Sponsors...

Family Money Drama

44| What About My Inheritance?

In today’s episode, we hear from someone who is wondering how (or even if she should) approach her parents about the inheritance her grandparents passed down. We discuss a completely different way to think about the situation to help her make the...

Careers & Money

43| You Aren’t Working Hard Enough

In today’s episode, we discuss a spicy and hot take on both sleeping and income. The question of the hour: are you even working hard if you’re not making a 6-figure income? Hear our thoughts and share yours with us after the episode!   Join...

Awkward Friend Issues

42| I Don't Want My Friends to Settle

How do you approach your friend when they are excited about a new opportunity but you know that they are capable of so much more? In this episode Allison and Chris help a caller navigate this delicate conversation and avoid any unnecessary...