My mom’s boyfriend, “Don,” is a walking awkward money dilemma.
Don earns a decent living, yet he’s an enormous tightwad. He mentally tallies who paid last and he isn’t shy about pointing it out.
When someone orders a round of nicer drinks for the table, he’ll then order something extravagant for himself — like a double Long Island iced tea made with top-shelf liquor. But when it’s his turn to cover the next round, he gets a pitcher of bargain beer for everyone.
It’s not even the cash that bugs me. It’s that this guy seems to think he’s being clever every time, and I want to call him out. Can you help me come up with something a bit more polite than “Hey, you stingy jerk, we saw that” the next time he buys a pitcher of Miller High Life after someone else splurged on premium cocktails?
I’d let it slide if he were strapped for cash, but he has way more money than anyone in my family.
P.S. Please, PLEASE don’t suggest avoiding drinking with Don. If you met him, you’d understand why that’s not an option.
Sincerely,
Drinking and Disapproving
Dear D and D,
Few things are more uncomfortable than parents dating people you can’t fully get behind.
I can imagine how frustrating it is when your generosity is met with this man’s particular brand of penny-pinching. Still, it’s not realistic to skip every family event forever. Don is going to be part of the picture unless your mom decides differently.
Have you tried bringing this up with your mother? She might be so smitten she doesn’t notice his cheap behavior crosses a line for you.
The worst outcome of that chat is she dismisses your complaints and you feel awkward about bringing it up. But that discomfort will likely be brief — you know what you’ve seen.
In the best scenario, your mom recognizes the pattern and teases Don about it. A lighthearted “Don, don’t be so cheap!” from her would carry a different tone than it would from you. Mom’s smile would soften it; your crossed arms and glare over that pitcher of High Life probably wouldn’t.
Another idea: Turn your dealings with Don into a personal frugality challenge.
Propose meeting at whatever inexpensive drink special a chain is promoting. Browse Groupon before you make plans. Use cash-back apps like Ibotta to find offers at bars and restaurants that offset Don’s penchant for pricey drinks.
Make it your own private mission: Can you out-thrift a thrifty person?
You likely won’t alter how Don spends (or withholds) his money, but you can make these aggravating moments more entertaining by trying to beat him at his own game.
The inbox is open. Send a question or your concerns to dear@example.com, and I’ll do my best to help.
Disclaimer: Selected questions and answers may appear in Savinly’s “Dear Penny” column. I can’t respond to every letter (I can only type so fast!). We reserve the right to edit and publish submissions. Don’t worry — your identity will remain anonymous. I don’t hold a psychology, accounting, finance, or legal degree, so my guidance is for general informational purposes only. I do, however, promise honest advice drawn from personal experience and observation.
Emma Blake is a senior writer at Savinly.
