Sometimes you run into a problem so tough, so awkward, so infuriating, you have to assemble all of your best and brightest friends to vent, commiserate and figure it out.

That’s the idea behind “The Group Chat.” We bring in friends of the pod to address your biggest money and job problems. For this installment, we were joined once again by NPR’s Julia Furlan, along with “Nancy” host Tobin Low. 

You can hear our first Group Chat here, and find a few highlights from our conversation below, edited for clarity and length.

OK, so I have a question about eating out. If I get a salad and everyone else gets steak, should I have to pay extra for someone else’s meal? What’s the etiquette for telling people you don’t want to pay for the extra drinks and appetizers they ordered? It’s annoying that the people who try to split the check are the ones who come off as cheap and not the other way around.

Julia Furlan: I feel like I have some spicy advice for this one … I think that you just have to do it. If you want to make a big thing of it, the cost is that everybody might think that you’re cheap. And that is sort of the way that the the world works right now, I don’t think it’s necessarily right. Just say it when you are ordering, not when the check is coming. You have to look out for yourself.

Tobin Low: I feel like Julia’s advice was the healthy, up-front, be-a-good-person model. I have a more stealthy piece of advice. Recently, when I’ve been out to eat, what tends to happen more often than a bunch of credit cards is one person putting down a card, and then saying “Everybody, Venmo me.” Then you have a little bit of control to say, “Cool, I owe you this much.” It just becomes like a tone-setter of like, everyone’s just paying what they owe.

I grew up in a lower-income family of eight where all my clothes were hand-me-downs and money was tight. Now, as an adult, I make more than both of my parents were making combined and I’m currently the most well-off among my siblings. That’s naturally led to some differences in spending — my wife and I bought a house a few years ago, and we just got a newer car and a brand new furnace. Everyone in my family only buys cars from Craigslist, and my brother-in-law couldn’t believe that I didn’t try to fix our old furnace first before buying a new one. I love my family, but it seems like our financial lives are growing apart, and I’m not really sure how to bring up things with them without seeming snobby. Any advice for someone in my situation? Thanks.

Furlan: There are a lot of things that happen when you move from one class to another. Just because you’re earning more money does not mean that everything feels simpler. I think that that’s something to acknowledge. I also think that your work here is boundaries. Like, a new car, a new house. These are things that your family will see, but they don’t need to know about your furnace. I think that your family doesn’t necessarily need to know every financial detail about your life, and that’s OK.

Low: Your siblings, your parents, those are complicated relationships. Sometimes, if you can see the trajectory of how things get interpreted, if you know that your sibling is coming at it from a place of jealousy or from a place of, “You have something I don’t.” If you can sort of remind yourself in those moments, maybe their reaction is still what it is, but the way you receive it can change.

I’m pretty well off and have a relatively well-paying job. But my husband has stage four cancer, so for the last year… to cover his medical costs … I’ve been dipping into our savings and following a tight budget. That said, recently at work, one of my colleagues asked me to pitch in $20 to get our boss a gift. But the thing is … I hadn’t budgeted for that … so I’m in this awkward position — either I can pitch in or stick to my budget, and pass. Since one of the issues I’ve been having at work is related to not feeling like part of the team, I put in the $20. But I still feel conflicted — should I talk with my co-workers about my situation, especially since I know it’ll come up again?

Furlan: My heart goes out to you. It’s just a heartbreaking thing. I don’t know your co-workers but it feels like a real basic human decency thing, if somebody says, “My husband has stage four cancer, our medical bills are crippling. My life is is difficult in this moment, I don’t think I can necessarily always participate in these in these team things …” Also, don’t buy a gift for your boss! Sorry, I don’t like that at all.

Low: And I think that she should give herself permission to also not shoulder 100% of the emotional burden of sharing here. I think a strategy could be, like, you find your one good Judy at work, who really gets it. And you sort of deputize them to be your representative when shit like this comes up. Because if there’s somebody who just knows what’s going on they can cut this off at the pass and say, “Hey, this is her situation. Can we just leave her alone?”