What’s Your Most Awkward Money Moment?

We've all had an awkward money moment or two in our life. Here is a cool inforgraphic outlining some of the more embarrassing ones to experience in life.

Happy Monday friends! With today being the first workday after FinCon15 I thought I’d keep it a little light while we are all still recovering :-).

We all have different views on money. When you throw in office politics, family members and random occurrences, it’s easy to have an awkward money moment from time to time. Awkward can be somewhat relative, though it generally has the same underlying result – you just want to cringe a little bit inside.

I found it interesting that several of the awkward money moments listed were related to working in an office. Now that I work from home I’m thankful not to be put in a situation again of feeling the peer pressure of giving to or buying something from every drive a co-worker’s child was doing. Not that I’m not charitable, I just don’t like spending money when I feel like I have to and it’s something I don’t need.

My Most Awkward Money Moment


I ashamedly would classify my most awkward money moment as what the majority did – getting a credit card declined. During my crazy spending days I had the opportunity to experience that feeling first hand a number of times.

I should have taken it as a wakeup call to stop spending like the world was on fire, but I didn’t. Instead, I found ways to get a little breathing room so I could spend more.

That being said, I found it interesting that there was nothing specific mentioned in the infographic related to family and money. I guess it depends on the family, but I’d guess in most families money can be an awkward topic to discuss.

We got to see that first hand several months ago when my Dad visited and we were discussing one of my brothers buying a condo. Mrs. Frugal Rules and I asked what they paid for the condo only to be rejected. Interestingly, my usually open and direct father would not tell us. To a fault, he’ll tell you anything you want to hear but when it comes to money it’s a different subject. It just goes to show you that what’s normal for one person is awkward for another.






Have you experienced any of these awkward money moments? What are some things that mortify you when it comes to money? Does your family openly discuss finances? 

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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more. If you're wanting to learn how to monetize your blog, check out my blog coaching services to see how I can help you take your site to the next level.


  • HATE awkward money moments! We had a bit of a one this weekend when we went to our local small town grocery store and some kids from our son’s baseball team were selling popcorn for their scout troop. I said we’d buy (and we did) but Rick about passed out on the spot when they said it was 20 bucks a bag. 🙂

  • Kim says:

    Our most awkward money moments ever are with my in-laws. I’m not sure if it’s more awkward to not help or to help them. Either way sucks and I suspect we will have more of those moments as time goes on.

  • We speak openly about it, but not everybody does! My in-laws side rarely mentions money at all. It’s definitely a taboo topic with them.

  • Kathy says:

    My most awkward money moment didn’t really have anything to do with my money. I worked at a doctor’s office who offered weight loss and nutrition classes. They were quite expensive and many people would pay with credit card. I had people’s cards declined which was bad enough, but then they would pull out more cards and say “put $50 on this card and $100 on this one” etc. I felt like telling them they really couldn’t afford this class.

  • Hannah says:

    Since I’m horrible with paying people back, I always try to pay the bill at restaurants. However, one time a friend covered my portion (I didn’t have cash), and I forgot to pay her back for months. It was embarrassing because she insisted that I would just cover her sometime, but it was all I could think about when I saw her, and I saw her all the time because she worked on the same floor as me.

    The burden of $12 debt could not be erased from my mind, and I cannot tell you how good it felt to finally remember to bring cash to the office one day.

  • The DeLeon says:

    A few months ago I was visiting some family in Canada. While trying to buy a family member a gift from Lululemon I had 3 different credit cards declined. It was bad enough getting 1 declined and I insisted the guy try twice more. I eventually had to ask him to set it aside and get cash. Talk about embarassing and looking like a mid-twenty guy in debt.
    About 3 hours later two of the banks customer serivce reps called and asked I was trying to make a purchase. I had to explain I was out of the country. They told me they would mark my file for the rest of the weekend and I was good to replace my purchase. Sorry, i told them, it was two hours ago and they had already embarrassed someone who had a clean record and never carried a balance.

  • I awkwardly have to decline girls trips with my friends regularly. I just can’t swing it with my current income and my commitment to paying off debt. That said, they’re becoming less awkward now because they are getting used to my declining!

  • I have one friend in particular who makes splitting checks when you are out as a group an awkward money moment every single time. It’s almost to the point where you just don’t want to go out with this person because you grow weary of all of the nitpicking over who ordered what and the exact breakdown per person. If I go out with a group, I know that I may win or lose when it comes to how much I pay, but I am open to splitting the bill equally because it’s the price of going out with a group.

  • I’ve definitely had my fair share of awkward money moments. I’ve had some awkward conversations with my Mom about money. It’s always strange when roles are reversed and you’re schooling your Mom about boys taking advantage of your money. 🙂 And there have been several instances at parties or whatnot where people have said derogatory things about financial advisors to then ask me what I do. Awkward!

  • Easily, the most awkward money moment I ever had was 15 years ago when I was preparing to propose to my soon-to-be fiancee (now wife). She was super smart with her money and had no credit card or student loan debt. I, on the other hand, had nearly run up the limit on 2 credit cards, was 1 year into a 3 year graduate program (funded by student loans), and didn’t really have squat to show for it except for some amazing stories from my travels when I was stationed in Germany.

    So, I had to confess my fiscal sins, because she was going to find out anyway.

    Fortunately, she was very accepting (as long as I didn’t make ANY MORE dumb decisions with my money) and together we tackled it and paid everything off by the end of my summer internship. Even better, she never held it over me.

    I got lucky.

    Did I mention lucky?

    (Hey, honey…are you reading this?)

    Even now, 15 years later, I get a little embarrassed thinking about it.

    But, embarrassment is a whole lot better than going into a relationship and tying the knot with someone only to have them find out AFTER the wedding that you have some financial sins to atone for.

  • A couple years ago when we were planning a bachelor party for one of my buddies everyone was throwing up different options for cabins we could rent. Everyone voted to get the one that had a small view of the golf course, even though it was going to be $40 more per person and we still couldn’t actually walk to the course. And of course there was the whole thing about being too hung over during the day to actually enjoy the view.

    I was the only one that brought up the fact that we should go for the cheaper. A little awkward but things could be worse!

  • I was having dinner with my friend whom I invited and my credit card got declined. The sad part is that I had no cash with me. It made me feel like what-the! In the end, I asked my friend to pay for our dinner and I paid her the next day. My awkward money moment.

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