6 Awkward Conversations About Money You Need to Have

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Money can be as taboo to talk about as religion or politics — but why? Yes, we are all financially flawed in some way. Yes, there is a stigma that money defines you. Yes, it feels really personal to have conversations about money.

But why does that stop us? There are plenty of things that are equally as revealing and uncomfortable that we openly discuss. Like our weight, our sex life, and our mental health, to name a few. We let our guard down in hopes of finding solitude in others’ responses, or gaining advice that can improve our current situation. Having conversations about money is awkward, but doing so leads to the same result as any other confession. A burden is lifted, and we find solutions.

Here are six awkward conversations about money you should have that you may not want to, but should. Like, soon.

awkward conversations about money with family

1. Your parents

I recently read a post Erin from Broke Millennial wrote that posed the question, “Are you your parents’ retirement plan?” It definitely struck a cord with me. I’ve seen firsthand children being left with the emotional and financial responsibility of caring for their parents. And it’s not easy, or cheap.

As millennials, most of our parents are nearing retirement. What plan do they have in place to support themselves for the next few decades? It might feel like you’re overstepping by asking, but if it comes from a place of love and responsibility, I think your parents will understand.

Ask them how they envision retirement, and how they plan to pay for it. You’ll also want to find out if they have a living will, medical power of attorney, life insurance and long term care insurance.

If talking about the possibility of your parents getting sick or needing an aid seems pessimistic or very gloom doom, I totally get it and sort of agree. But at the same time, I know for certain that not being prepared when hard decision making is needed is worse. It’s much easier to muscle through a difficult conversation than deal with these questions in the middle of an emergency.

awkward conversations about money with family

2. Your siblings

If your parents divulge that you are in fact their retirement plan (or if their lack of plan insinuates they are going to need you more than they think), you need to take action. If you have siblings, that action should include them. As a team, you need to discuss your savings plan. How much can each of you set aside to help your parents in retirement? How will the burden be distributed among you? Who can handle what? Will you each hold onto your own contribution, or will you pool the money into one account?

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Remember, this isn’t a blame game. You may be disappointed in your parents because they didn’t plan as they should. You may think the oldest sibling or the sibling with the biggest salary should just handle it themselves. Try not to create rifts and think of this as a team effort. Also be grateful you know what you know now, so you can plan for the future rather than react to it later.

awkward conversations about money

3. A professional

A few years ago I was diagnosed with a rare skin disorder that left me with some pretty nasty scars. I fought myself for years about it, never totally accepting the change in my appearance or how it affected my confidence and emotions.

Finally, after some nudging, I went and spoke with a counselor. Getting an outsider’s perspective allowed me to see my situation much differently and gave me a safe place to completely communicate my concerns. Suddenly my fears didn’t seem so scary, and I learned easy, actionable ways to build back my confidence.

A financial professional, whether it be an advisor or a Wealth Coach, is similar in that they can address your concerns and provide you with a game plan to achieve your goals. We often think we can handle things ourselves. (Even with my scars, I always felt like eventually things would get better or I would figure things out.) But sometimes we just need help, and a professional in that field can be the key to seeing real progress.

I’m not saying you can’t learn about personal finance on your own. But having conversations about money with someone that has the education and certifications to advise you on interest, investments, home and student loans, taxes and more can be a huge game changer. Don’t let stubbornness or the awkward idea of sharing with a stranger stand in your way of getting the help and guidance you need to stop stressing about money and take action.

awkward conversations about money with husband

4. Your sig other/bf/gf/fiancé/husband/wife

Is there a right time in a relationship to have a real talk about money? No, but the sooner the better. If you see yourself sharing a life with this person, it’s important to know if you are financially compatible.

There are a few layers to money in a relationship. One big one is spending habits. If you are a savvy saver and your sig other is a big spender, conflicts can arise. That doesn’t mean you can’t find a middle ground, such as a reverse budget™ (where you save first and then spend as you please) or setting up a fun fund (putting a percentage of your earnings in an account for dates, vacations, etc.). But you do need to have conversations about money that address each other’s spending habits. If they are different, you need to determine how (and if you’re willing) to comprise.

Another big topic is debt. Do either of you have any? You need to be honest with each other about student loans or credit card debt. If you end up living together or getting married, these payments will effect what you can afford. Having debt isn’t a crime, so don’t be afraid to ask if your partner does or admit that you do.

Goals are also an important layer to cover. What are you saving for? You may agree on saving but not for the same things. The old, “Where do you see yourself in five years?” is an indirect way of finding out if your financial goals are aligned.

awkward conversations about money with friends

5. Your friends

Having conversations about money with your friends can feel like torture — especially if the convo is about you not having any. There is often guilt associated with admitting you need to spend less, and then following through with it.

A good tip is to lead with a goal. No one wants to say, “I’m broke.” Instead, tell them why you are cutting back. Are you trying to pay your student loans off faster? Buy a car? Afford an upcoming vacation? Let your friends know why they won’t see you throwing back drinks at the bar or out to sushi for awhile. It’s easier for people to understand that you are trying to achieve something, than understand why they aren’t a “priority” in your new budget.

Once you’ve explained your current situation, offer more affordable alternatives for spending time together. This will solidify that your changes are about your financial goals, not your friendship. You may even motivate them to get more serious about money as well.

awkward conversations about money

6. Yourself

Talking to yourself about money isn’t weird, I promise. You may have even heard of a money blueprint already. Basically it requires you to take an honest look at how you want your life to be. Everyone has different goals and those goals determine your money blueprint.

Yours may be to get married, buy a house and have kids. Your best friend’s may be to travel as much as possible, as soon as possible. You and your best friend have very different money blueprints because in order to meet each of your goals, you will need to save, budget, and invest much differently.

Once you’re set on what your financial goals are, you need to figure out how you’re going to stay accountable. I’m a big advocate of writing goals down, and revisiting them weekly or daily. However often you need a reminder or renewed motivation.

Our money mindset is sometimes a predisposition, whether our parents, community or media influenced it. If we want to change our behavior, do something different, or strive for a lofty goal, it is going to require dedication. Having a talk with yourself about what you want and how you’re going to get it is one of the awkward conversations about money we all need to have.


Invibed is an online destination that makes personal finance relevant, accessible and entertaining to millennials. Follow Invibed on Instagram.


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