My Mom’s Stingy Boyfriend Has a Sneaky Way of Avoiding Pricy Drink Tabs

Hands holding drinks click them together in a toast at a bar.
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Dear Penny,

My mom’s boyfriend, “Don,” is a walking awkward money dilemma.

Don makes good money, but he is a huge cheapskate. He keeps a running list in his head of who picked up the last tab, and he doesn’t hesitate to call people out.

But whenever we go out for drinks and someone orders a round for the group, he orders something pricy like a double Long Island iced tea with fancy-schmancy top-shelf liquor. Then, when it’s his turn to buy a round, he orders a pitcher of cheap beer for the group.

It’s not even the money that bothers me. It’s the fact that this jerk thinks he’s outsmarting us every time, and I really want to call him out on it. Maybe you can help me come up with something a little more polite than “Hey, you chintzy jerk, we know what you did there” the next time he springs for a pitcher of Miller High Life after someone else has paid for quality libations?

I’d give him a break if he were hurting for money, but he’s got way more of it than anyone in my family.

P.S. Please, PLEASE don’t suggest activities that don’t involve drinking with Don. If you met him, you’d get why that’s not an option.


Drinking and Disapproving

Dear D and D,

The only thing more awkward than parents dating is when they’re dating someone you’re not totally rooting for.

I’m sure it’s disappointing when your generosity is met by this guy’s intense sense of frugality. But, as you know, it’s not like you can just bow out of every family gathering for the rest of your life. Don’s going to be around, in whatever capacity, unless your mom decides otherwise.

Speaking of your mother: Have you tried discussing your concerns with her? She may be so enamored with this guy that she doesn’t realize he’s being cheap to the point of upsetting you.

The worst-case scenario of that conversation would be that she doesn’t see her boyfriend as being stingy at all, and then you’ll feel bad. But only for a little while. Because you know deep down that he’s stingy.

In the best-case scenario, she’ll pick up on Don’s habits and start to rib him about it. A playful “Don, don’t be so cheap!” coming from your mom would sound a lot nicer than if you did it. Probably because your mom would smile as she said it, while you would be arms-crossed scowling at him over the top of that pitcher of High Life.

Another alternative: Use your interactions with Don as an exercise in your own frugality.

Suggest the group go out for whatever cheap drink Applebee’s is serving up this month. Take a spin through Groupon before making plans. Check Ibotta for cash-back deals at bars and restaurants that can make up for Don’s Long Island habit.

It’ll be your own private quest: Can you outfrugal a frugaler?

You may not be able to change how Don spends his money (or chooses not to spend his money). But you can keep these maddening interactions entertaining by attempting to best him at his own game.

The inbox is open. Submit a question or send your worries to [email protected], and I’ll see what I can do to help.

Disclaimer: Chosen questions and featured answers will appear in The Penny Hoarder’s “Dear Penny” column. I won’t be able to answer every single letter (I can only type so fast!). We reserve the right to edit and publish your questions. Don’t worry — your identity will remain anonymous. I don’t have a psychology, accounting, finance or legal degree, so my advice is for general informational purposes only. I do, however, promise to give you honest advice based on my own insights and real-life experiences.

Lisa Rowan is a senior writer at The Penny Hoarder.