Gold Digger or Using Common Sense – Looking at Partnership & Money

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Hey Wendy,

I’m in good financial shape and I’m a bit worried about the financial situation of the new guy I’m dating.

He might have pensions, and he still sells a little real estate here and there, but he just put his wife in a long-term facility due to advanced Alzheimer’s. This is probably costing $3,000 per month.

He says I “look expensive” but not in a critical way. He says he’s head over heels for me. The problem is I don’t want someone who can’t carry his own weight and who is able to do the kinds of things I want to do. I’m in my late 60’s and he’s in his early 70’s. How do I go about finding out without sounding like a gold digger?

Thanks for your help, Wendy!

Debra J.


Hey Debra,

Gold Digger: A person who forms relationships with others purely to extract money from them, in particular a woman who strives to marry a wealthy man.

Debra, that’s not you.

You, my dear, are looking for a mate who can match where you are in life. Someone who won’t drain your savings to live out a happy retirement with you. And that’s 100% acceptable.

Before we get into the nitty-gritty here, I want to say my advice for you is different than it would be if you were, say, thirty-five. You two don’t have decades of work life in front of you where you could predictably expect ups and downs, pivots, and gains and losses with employment and finance. Retirement is a gamechanger, so this response is tailored to your current life stage.

Your Money is Your Money, and His Money is His Money

Let’s start with the end-of-life care for his wife. $3,000 per month would be a steal, so I think you’re low-balling it. I know three people in permanent/long-term memory care residency right now and they pay upwards of $8,000–$10,000 per month. It’s heartbreaking. The good news is the exact amount he pays for her care is not your business—not now, not ever. At this point in your life, you’re not looking to comingle your money.

You Are His “Ten”

You can translate “Head over heels” as you are his “Ten.” And when a guy is head over heels for a Ten, he will do/be/say anything to get her. A Ten will turn a 70-year-old man into a teenager again. Have you ever had a guy friend who was running after a Ten, Debra? It’s obnoxious. Especially when that woman isn’t giving your friend the time of day. It’s hard to watch. That guy will pretzel himself up into whatever she needs him to be. He’ll spend money he doesn’t have. He’ll brag about accomplishments he hasn’t achieved.

Can you remember a guy you just had to have? You might have done or said things to attract him that you look back on from between your fingers. We humans go a little nuts for the ones we have intense chemistry with.

So, while this might feel good for you, as the Ten in question, you have some added responsibilities if you want this to go well.

Responsibilities of a Ten

Like any woman in a relationship, you must speak your needs, wants, and desires aloud.

And as his ten, you need to watch out that he’s not dismissing his own needs and making it worse for both of you just to give you what you desire.

A question to practice asking that addresses this issue is, “Are you sure that works for you?”

You Look Expensive.”

Up next: What does that even mean?

This is your perfect opener, Debra.

You could say in your most curious tone, “Hey, the other day you said, ‘you look expensive’. It had me wondering, what did you mean by that?” 

After asking the question, do not dialogue—simply zip it and listen to what he has to say. Even if sitting in silence while he thinks is uncomfortable, don’t speak until he’s given you a satisfactory answer. If he gives you a short one like, “oh, I don’t know…” keep sitting in the silence with open body language and a neutral expression. I promise, he’ll come back with more. When he has the space to speak honestly, he’s most likely going to say something like, “I don’t think I have the kind of money that will make you happy.”

Once he’s laid something down, the money conversation is open for discussion.

This is your big opportunity to talk about baseline needs (think of your ‘enoughs” as the foundations). You want to go all the way up to your wildest dreams if you had it all your way (the ceiling). And once you two have had a chance to share your own vision of what “enough” looks like and what your wildest dreams are, that should give you both a pretty clear idea of whether you’re standing in the same room or not.

A Relationship by Design

Debra, there’s nothing wrong with wishing to be with someone who can do all the things you want to do, especially at this stage in your life. If you’d hoped to spend your retirement traveling and you’ve structured your finances to do that, you should do that. I’d like you to consider, though, that if he is an amazing guy for you and you’re a great match, you two are grown-up enough to structure your relationship any damned way you want.

If he has less money for you, but enough for home life, maybe he’s your companion at home. And maybe you travel the world with your favorite gal-pal who has means similar to yours, or you could take off adventurously on your own.

If both of you like that plan and he wouldn’t be pouty about it, there’s no wrong way to structure your life. You’re old enough to know you don’t get all your needs met by one person alone—it takes a village.

There’s way more to partnership than money, so what else do you need from a partner? As you’re dating, whether it’s him or others, make sure he meets all of your have-to’s. I’d take an afternoon to do my Partner Have to Haves workshop exercises to see if this guy is a good match for you, or, if no, what else to look for in the next round.

Good luck!

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