Should I Marry a Kind Loser?

Scott,

I have my own company that’s worth a bit of money, and I own my own home and car. I earn $250,000 a year. However, I’ve been dating a guy for about two years who doesn’t have anything. He earns the minimum wage, can’t save, and is consistently struggling. Everyone I know keeps telling me to leave him. Yet he is the kindest soul and my best friend – he’s had a really rough upbringing and just keeps hitting bad luck. Still, I’m scared he is going to live off my back the rest of my life. I’m 30 now, and I want to get married. But should money be the deciding factor in this relationship?

Mary

Hi Mary

Let me be clear: I’m a finance guy, not a relationship coach.

To me, dating is like shopping at IKEA: everything looks cute and stylish under those soft Scandinavian lights. You stroll through the aisles, picturing how perfect it’ll be in your home.

Marriage is like dragging the flatpack home, realising the instructions make no sense, and discovering – halfway through assembly – that you’re missing three screws and the whole thing is lopsided.

Right now, your guy is that wobbly, half-built Billy bookcase – no savings, no financial stability, and no clear plan. Maybe he can pull himself together. Yet you’re not his Allen key, Mary. 

If he truly loves you, he’ll prove it. Hand him The Barefoot Investor and give him three months to get a better job, start saving, and show he’s serious about building a future with you. What if he can’t?

Well, you know what to do with wonky furniture that won’t stand up on its own – dump it on the nature strip and move on.

Scott