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My boyfriend can’t pay his rent, but still won’t stop buying rounds of drinks for our friends

  • Author: Wayne and Wanda
  • Updated: November 16, 2019
  • Published November 16, 2019

Dear Wayne and Wanda,

I guess my problem is a good problem to have, but I still need advice. In simplest terms, my boyfriend is just too generous.

Anytime we are out with a group of people, he insists on buying a round of drinks, even if no one else does. Often times on a night out with friends, he will buy a round of shots, on him, which can easily come up to $50 or more. When we have lunch or dinner with people, as soon as the bill comes, he throws his card down — he doesn’t even give anyone a chance to consider paying. And if anyone does offer, he always insists.

If he had tons of money, this wouldn’t be such an issue. But he doesn’t. I know for a fact he’s in debt and has several credit cards near their limit. There have been months when he couldn’t quite cover his share of the rent so I covered for him. We have lived together for a few years and generally speaking, he often comes up short on his end of expenses — yet he never hesitates to pay for huge groups when we’re out with our friends. He doesn’t see how the two are connected. But I think it’s crazy he continues to pay for our friends — who can afford their own drinks and who have perfectly fine jobs!! — when he sometimes struggles to pay for basic expenses.

We are going on a trip soon with three other couples and I can just imagine it now, my boyfriend paying for drinks and dinners night after night. It will bankrupt us! How can I explain that this is a huge deal to me? We talk about getting married when we’ve saved enough to start our lives together, but he isn’t presently saving any money, at all. Help?

Wanda says:

In the business world, there’s something called principled negotiation and practicing it can do great things for relationships. In layman’s terms, the idea is when two people negotiate, they typically dig in on their stated position, and things fall apart. In this case, your boyfriend’s position is, “I will keep buying things for my friends!” Yours, contrarily, is, “Stop buying everything for everyone!” Where’s the deal to be made?

Principled negotiation encourages us to look past our stated positions to what our interests are to find mutual ground. Imagine two people fighting over a lemon; each wants the lemon for himself. That’s their position: “I want this lemon for me!” But discussing this further, and getting past the “what” to the “why,” it turns out one wants the lemon zest for a pie, and the other wants the juice for a cocktail. See? They can share the lemon! They just had to get past positions to figure out what their interests were and find a mutual win.

So what are your boyfriend’s interests? I’m guessing being broke isn’t one of them, nor is having to ask you to cover his bills every month. That’s just embarrassing. We could guess his interests are around making people happy, being generous, and doing nice things for his friends. Yours are around not blowing the budget, and having long-term sustainability to meet your #couplegoals.

Discussing these interests at the heart of your positions (and behaviors), you can hopefully find a middle ground. Maybe instead of so many nights out, you can co-host an awesome dinner party once a month? Or agree that a round of shots is a great way to make people happy, and just as effective as footing an entire dinner tab. The bottom line: nagging will not stop your man from playing Santa at tab-paying time, but getting into his generous head to understand the motivation behind his generosity just might.

Wayne says:

When Wanda gives you lemons, I give you relationship advice lemonade. And your boyfriend, apparently, is buying every cup at my stand! Sweet!

Whether your boyfriend is a people pleaser, a party person or a lush who loves living lavishly really doesn’t really matter anymore. Ultimately, if you two are going to be partners in money, mortgage and marriage, his spending issue is your spending issue, too. Binge spending and drinking. Drowning in debt and denial. Not exactly the foundation of a fruitful future. He needs to truly appreciate that every time he makes it rain for the homies, your already porous partnership springs a larger leak.

How serious is this? So serious that the next time party night rolls around, he’s going to have to sit at boring home with you, open an Excel spreadsheet, tap the calculator app on his phone, and make a couple’s budget with you. Whoop whoop! Scour the past few months of bills and purchases. Look at the income and expected spending over the months ahead. Factor in all the debt. Heck, make a special tab for a savings goal: your wedding.

I’m hope the number-crunching is a sobering moment of clarity for your lit little dude. But don’t let him get depressed or discouraged. Spend time online researching savings tips. See if your bank or credit union offers financial adviser time for even more personalized insight. Hopefully, less impulse spending, fewer nights out, and smarter saving will put you both in a better space fairly quickly. And then, when you can see some progress, tell him it’s cool to buy one round for the crew.