Ask Wendy

Handsome, Talented, & Broke

Friday, December 18, 2020
Hey Wendy,

I met a wonderful man in July. He’s a classical musician, and he’s just moved back to NYC and found his dream job. Problem is it doesn’t pay well but it comes with some great perks (apt in a great location and health insurance). And he has a ton of student and consumer debt.

So far, I like him a lot! We have similar values. He treats me well. And I feel emotionally secure with him. He seems to be the guy I’ve been looking for for the past 30 years.

I thought being financially secure was one of my requirements. His plan was to take on projects to supplement his income, but now due to pandemic new musical projects are likely delayed for a year.

Do I stay in this relationship and assume he’ll figure it out? Or should I cut the cord now before I get further attached? I am financially secure, but I don’t make enough to support both of us. Thanks for your advice.

Susie E.

Hey Susie,

I’m so glad you’ve found love in COVID times. Good for both of you!

I definitely understand your desire for financial security; it’s a great goal, for sure. And if it’s a top value for you, then decide what your “enough” looks like and find that line. From there, you can chat with him about it and see if you’ll ever align on this, or if you’re fundamentally incompatible because he’s not able to reach the height of your “enough” line.

You may decide to uncheck the “financially secure” box on your requirements. He’s amazing. You’re compatible in all the important ways. And you might just let this one go. But if you do, you’ll still need to have a conversation about money.

Your Deal-Breakers Are Valid

Before we get into the “what to say and not say” part, I want to address your choice. Finances and safety are personal matters, and I won’t judge you either way. We all get to decide what’s right for us when we partner, and your deal-breakers are yours. Don’t ever let someone else tell you what your deal-breakers should or shouldn’t be.

Okay, back to what to say.

How to Start

A good starter would be something like, “Hey, I know your financial situation isn’t really any of my business, but if you’re willing, can we talk about what life looks like from a financial perspective if we stay together?”

What to Say

From there, share what you can do, what you can’t do, what you might do, and what you should definitely not ever be counted on for doing. You can tell him what scares you — in this case, honestly up front is the way to go. For example: “I can’t support you. And if you’re really struggling, it’s gonna freak us both out.” Because even when you both know you can’t help, him being underwater is going to make you feel unsafe and off-balance.

What Not to Say

Don’t share what you wish for when it’s not who he is. This includes comparing him or his profession unfavorably against other people, including you. Example: “I really wish you had a steady 9–5 that was more in line with my salary” or, “I wish you would have gotten that last job.”

The Breakdown of a Hard Conversation

When it comes to the tough stuff, we worry we might hurt a guy’s feelings. And yeah, you might. But conversations like this are needed and real, and they’re not emasculating. Telling a man what you need is not emasculating, even if he can’t provide it. So, sharing needs, boundaries, and potential scenarios (even the uncomfortable ones) are all in-bounds as long as you’re doing it from a place of “hey, we’re in this together and just trying to work it out” instead of a place of blame or critique.

What doesn’t move a conversation forward in a productive direction is (as stated above) talking about things that are out of the scope of what he feels is possible. And if you’re not sure what he thinks is possible, then ask during your chat.

“Love is All You Need” is Bullshit

Love is pretty great, but you definitely need more than love to have a happy life in which you feel safe. You need a partner, and partnerships start when everybody is doing their part. A partner is someone who is competent at adulting and managing their life.

No one expected 2020, and we’ll continue to deal with and unravel this fucker in 2021 and beyond. External circumstances clearly played a part in your dude’s financial conundrums, but how does he manage in a crisis? How does he manage when his options are taken away? And how fast can he pivot?

Financial Security is an Illusion

We can do all we can to plan, save, and invest wisely. But, as you know, sometimes the hand of fate is cruel and can foil even the most careful saver’s life.

Personally, back when I was doing the picking-a-partner dance, I didn’t pick for money. I passed on plenty of guys with money. Instead, I picked on drive. Because nothing is a guarantee, and money comes and goes. I needed someone with a lot of drive, a sharp mind, and an ability and willingness to pivot hard when required. I’m glad I did, too, because for me, these are also qualities I have a lot of respect for. So, when I see them in action, it’s uplifting (and kinda sexy), even if the circumstances are scary (like when he’s hopping to a new job — they do that a lot in tech).

Discover His Process

So back to you. While we can’t guarantee a job, a side-hustle, or a steady income tomorrow, you can look for clues on how he does manage finances and obligations. How did he get that dream job? Did it come fast? Was it luck or grit that landed it? A New York apartment in a good neighborhood is a huge bonus, right? How motivated is he to make something else happen for himself? What limiting stories is he telling himself as “truths” that get in the way of what he wants? Is he good at coming up with a plan B, or does he stick with a failing plan A? And, is his plan realistic in non-pandemic times?

You’ve got a hard decision here, and the only right answer is the one you come up with after having weighed the pros and cons. I hope I’ve given you enough to work with to get on the path of discovery.

Good luck!

Wendy Newman is the author of 121 First Dates. She’s a dating, sex, and relationship expert who’s led hundreds of workshops and revolutionized the lives of over 70,000+ women internationally.

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