This Is Awkward

Awkward Episodes

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...

Debt Troubles

41| About Those Student Loans...

In today’s episode we hear from someone who has an awkward encounter with their mom about paying for college. We discuss the conversation that took place and how we have ultimately changed the way we see our parent’s past decisions. Join Us On...

Relationship Problems

40| Is It The Thought That Counts?

In today’s episode we hear from someone who received a gift from her husband, but he clearly overpaid for the gift. Should she tell him that he overpaid and return the gift or should she let him think he got a great deal?   Join Us On Patreon...

Relationship Problems

39| Honey, We Need To Talk

In today’s episode we hear from someone who is nervous to approach her husband about a change in their debt payoff journey. She shares her concerns and asks for the best way to start a conversation about such a big financial situation.   Join...

Relationship Problems

38| I Can’t Keep Up Financially

In today’s episode we hear from someone who doesn’t make as much money as their partner, nor did they grow up with as much family wealth. Now that they are living together, they are faced with how to have an uncomfortable conversation about how...

Awkward Friend Issues

37| If You Flake, I'm Billing You!

In today’s episode we are discussing the proper response when someone is a no show for a wedding after they sent an RSVP that they were attending. One couple went so far as to create an invoice to send their no show guests for the cost of the meal!...

Careers & Money

36| I Make Double Her Salary

In today’s episode we hear from someone who realized that he makes double what a female coworker with similar job title and experience makes. We dive into the gender wage gap and steps he can take to help close the gap at his workplace.   Join...

Awkward Friend Issues

35| You Could At Least Give Me Half

In today’s episode we hear from a caller who has a friend that wants them to use their affiliate link for something and isn’t willing to split the money they make from the link. This brings up a good question: when it comes to affiliate links,...

Careers & Money

34| You Make How Much?!

In today’s episode we discuss how to handle the question “how much money do you make?” Whether you’re an open book or more private when it comes to your finances, we talk about what to consider when answering this question. Also, Chris gives a...