Awkward Episodes

What do you do when you go out to eat with your parents and they are the world's worst tippers?  That's the dilemma facing our anonymous writer this week. Their parents have a tipping rule that hasn't changed in 20 years, and while it might have...

Have you ever been in a situation where you let someone move in to save money, only to regret it later?  That's exactly what happened to our listener. They let their fiance's friend move in to their house to save money on rent, but after losing...

That's the predicament our self-employed listener is facing, and it's driving them crazy! Despite several reminders, the client keeps delaying payment, and our listener is unsure how to handle this weird behavior. Join Us On Patreon Get access to even...

Can you put conditions in place before you agree to marry someone? This week Chris and Allison dive into a listener's cringe-worthy story about a coworker who demanded his future wife pay off her credit card debt before they tied the knot. Listen in...

Join Us On Patreon Get access to even more bonus content with our This Is Awkward Patreon starting at just $3!     Allison's brand new book Money Made Easy just released today! So in honor of her new book Chris has prepared a dramatic...

It feels like we get a million tax forms in the mail every year. In this special bonus H&R Block Tax Tip episode lets breakdown 3 of the most common 1099 forms that you should be on the look out for each year.   Today's awkwardness is...

Have you ever found yourself in an awkward situation with a family member that also happens to be your financial advisor and broker?  In this episode of our podcast, we discuss a listener's question about their complicated relationship with their...

Have you ever struggled with feelings of fear and stress around money?  Growing up in a household where discretionary spending was not an option, our listener felt like a financial burden and was hesitant to spend even the few dollars they were...

How do you figure out what is a fair amount to pay your mom in rent? This episode's question comes from a listener who moved in with their aging mother after struggling to find a job after graduating college. They've been paying $700 in rent ever...

Struggling to manage a co-owned property with a partner who's facing financial difficulties? You're not alone! This episode is for anyone who's experienced the frustration of carrying the financial burden of co-ownership. Join us as we hear from one...

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....

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...

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...

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...

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...

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...

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...

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...

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...

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?...

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...

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...

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...

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...