Should I Marry a Man Who is a Late Bloomer?

I’m 36 and he’s 38. We both want to get married and have kids. He finished grad school 2 years ago and so he’s only been working in his new profession for 2 years. He was doing odd jobs before that and so he doesn’t have any savings, but he does have student loans. I’ve been working and saving for 15 years and I’m finally in a place professionally where I’m making OK money for the first time in my life. I don’t have a lot, but I’ve been carefully putting money aside, while also helping my mother out. While I’m not crazy about the fact that my boyfriend has no money saved and actually owes thousands of dollars, I love him very much and I accept this fact about him. He’s had life experiences that have made him the man who I love today. I am more interested in how he’s going to move forward with his life from this point on. But here’s where I don’t see him being proactive and I’m not sure how to handle it or how poorly it bodes for our possible future together.

As I said, I’m already 36 and if we are to wait another 1.5 years until we get married (as you recommend) I’ll be almost 38 and kids will be around the corner. We’ve talked about about this timeline for marriage and kids (if we decide that we want to be together) and we’ve started talking about our finances and his career plan for the next 3 years. He says that he could make about 20% more in his next job, which would be life-changing for him. He’d be able to pay off his loans far more quickly, get far more affordable health-insurance, be able to work on exciting new projects. Maybe we’d even be able to go on vacation in Europe instead of just dreaming about it! But so far it’s just been talk.

I’m not a therapist, but based on what he’s told me, I think part of the reason that he’s dragging his feet is because he’s conscious of his age and feels embarrassed by the fact that he’s 38 and looking for a lower-level job in his field. I have told him that people change careers all the time. I feel that I can help bolster his confidence and I am happy to do it–my last boyfriend did that for me and his confidence in me really helped me take the next step I needed to in my own career. But my question is how do I create a supportive environment and make him feel totally accepted, while also making sure that I get what I need–which is seeing that his is doing what he needs to do to help create the conditions for us to start a life together? I know that men don’t like to be pressured (who does??) and I don’t want to give him an ultimatum, but I need see that he’s serious about moving ahead professionally, both for his own sake and for ours. But I also want him to feel motivated on his own.

Sorry that was long and a little convoluted. I don’t want to sabotage this great relationship because I’m scared of investing precious time into a relationship that may not pan out. But I also want to be clear with him about what my expectations are. And yet I know that some things need time to play out. I am struggling with how to balance these things.

Thank you for all your sound advice and ample wisdom!

Ready for Lasting Love?
Ready for Lasting Love?


Flip the genders and you have a pretty similar picture of my relationship a decade ago.

I was 36 and was finally starting to make and save money.

My girlfriend was 38 and $40,000 in debt.

I was taking control of my life as an entrepreneur.

She was working at the same company for 14 years without health insurance, making less than 60K/year.

That’s the simplistic view, anyway. In reality, everything is more nuanced. My wife’s debt was largely the result of a divorce where she received no alimony because her ex lost his job, and the fact that she took $15,000 advance on her credit card to help her best friend who was facing eviction. In other words, my girlfriend wasn’t a profligate spender; she was just in a bad situation.

Her job, while not lucrative, offered a comfortable work environment with women she loved and incredible five-star travel perks.

Once I accepted who she was — my favorite person on the planet — we could start building our future together.


Even so, my default was to be critical. After all, I’d never accrued a dollar of credit card debt. I’d never work at a company without greater financial upside and insurance. But here’s the thing: my girlfriend was a great human being who was content with her life choices. She didn’t need a prestigious job or aspire to greater things. That was MY narrative and I had to consciously not impose it on her. Once I accepted who she was — my favorite person on the planet — we could start building our future together.

For us, it was me, paying for everything for nearly 3 years while she paid down her own debt to get back to even and clear her credit.

For you, it will be determining if you’re content with a husband who may not be a worldbeater, but is a wonderful man in every other way. If, in fact, he aspires to a job where he makes 20% more, it’s within his reach, and you believe in him, I see no reason for you to abandon ship.

It sounds to me like a good heart-to-heart is necessary — the equivalent of reading him the letter you just wrote to me. You don’t want to pressure him. You don’t want to offer ultimatums. You don’t even want him to change. You just want to know that if you’re investing your future in him that you want the same things out of life, which includes a greater level of financial stability. If, after he tells you that he’s on the same page, he continues to drag his feet instead of getting his ass in gear, you’ll know who he really is.

And THAT’s the point where you’ll have a real decision to make.

Good luck.