Awkward Episodes

After a far too long break, the final episode of This Is Awkward is here! We decided to go out in style and prepare a double episode for you all. In this final episode we are covering two very awkward …

What happens when the college fund becomes the kitchen fund? Our listener's is in a tough spot: their 20-year-old daughter, after a year-long college hiatus, decides to hit the books again. But there's a twist—the $30,000 set aside for her …

Have you ever had a friend or family member who's a total social media faker? You know the type, portraying a lavish lifestyle online, but you know the real deal—they're broke and those fancy trips and purchases just aren't happening. …

Have you ever felt like your bank account's getting worn out by going to weddings faster than you are? This week we are hearing from Kate who we got to talk to in person. She's in her mid-twenties and swimming …

This is a special episode of This is Awkward recorded in Denver Colorado! Does the audio sound a little weird... yes, but we are weird so it works. This week Chris has devised a special game for Allison called Would …

Ever felt like your kindness was being taken advantage of Dive into today's episode where one listener unveils a family dilemma: their sister-in-law using their nanny for free! Confronting her sister-in-law led to family tension, now she...

How much would you let your kid spend on a prom dress and the pure luxury of a 100 finger massage We dive deep in to the world of luxury once again in another episode of Ain't No Way! This …

Have you ever found yourself competing with your partner's family for financial support? Today's episode explores a sticky situation where our listener, expecting a baby, finds her boyfriend funding his sister's reckless lifestyle, even after she...

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How much would you be willing to spend for a few moments of peace in a dormant volcano? We dive deep in to the world of luxury once again in another episode of Ain't No Way! This week Allison is …

Ever found yourself torn between helping out a loved one and protecting your own financial future? On today's episode, we're diving into a real dilemma. Our listener's mom, despite being the world's best, is drowning in credit card debt and …

This is Awkward is moving to 4 times a month with our new episode called Ain't Now Way! You're probably wondering what this is all about. Let us paint a picture for you. Have you ever been scrolling online and …

In our first episode back, we're diving into a story from a brave Physician Assistant who recently fought for and won some well-deserved workplace perks. But now that they've got them, they're not quite sure what to do. Have you …

Listen to even more with a 7 day free trial at from Uppbeat (free for Creators!)

Listen to even more with a 7 day free trial at from Uppbeat (free for Creators!)

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 …

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 …

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 …

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 …

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 …

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 …

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 …