Dear Penny: My Friend Constantly Brags About How Much He Could Make. Why?

Two male friends have a conversation over beer.
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Dear Penny,

For the past 1½ years, my friend always asks me the same questions when I see him. I see him six to eight times a month.

He asks how my job is and if I will be looking for a new job soon. I provide various responses depending on my mood — mostly positive. He then tells me that he is considering a new job. He either says “I can pretty much name my price anywhere” or “I want to make $500K”.

I don’t mind these questions, as I am happy he’s doing well. But I don’t understand why he needs to bring up the same conversation every time we see each other (literally every time). Is this in my head? I feel like he doesn’t care about asking about my job — he just wants to talk about himself.

— Bugged by Bragging

Dear Bugged,

Have you asked this same question to your friend? He’s the best person to tell you why he feels compelled to steer the conversation in this direction, so bringing it up in a gentle way could help you get the answers you’re looking for.

You don’t have to be accusatory or even suggest that he doesn’t care about your job. Next time he leads you through this thread of conversation and tells you he’s considering a new job, maybe say, “Yeah, you’ve mentioned that quite a bit. Why has it been coming up for you so much lately?”

The Penny Hoarder with

It’s possible he *does* just want to talk about himself. It sounds like he’s itching to talk about money or work for some reason. Maybe that’s because he wants to show you how well he’s doing, or maybe it’s because something in his relationship with money isn’t feeling right for him, and he’s looking for a space to work it out. Consider the details of your conversations, and try to nudge those feelings out by asking for more: What’s holding him back from going after a new job? Why is the salary so important for him? Who else could he have this conversation with?

Our culture makes money a taboo subject, so there aren’t many established ways to bring it up in a conversation, and he might not feel comfortable talking about it with many other people. By following up with some open-ended questions, you can invite him to tell you more about what’s happening in his relationship with money. (And by noting that he’s mentioned this to you before, you can also help him realize he’s being repetitive.)

Dana Miranda is a Certified Educator in Personal Finance®, author, speaker and personal finance journalist. She writes Healthy Rich, a newsletter about how capitalism impacts the ways we think, teach and talk about money.