My partner of 3.5 years wants to get married, and although I love him, I’m hesitating—for financial reasons. He’s an amazing companion and tries hard to do nice things for me (brings flowers, cooks, grocery shops, etc.), but he earns about $30,000 as a chef, owes $100,000 in student debt, and seems perfectly happy with that. I’m a teacher, work 2 jobs, own a house, and will have my student loans paid off in the next 18 months due to my hard work. Is love and companionship worth the financial stress? I’m 42, and this would be a first marriage for us both.


Dena G. I’d kill for a chef boyfriend but…..a chef boyfriend who is laissez faire about owing money not so much. Maybe it’s not a big deal in the scope of things but how people handle $ says a lot about how they handle other things. I’m not sayin’ to throw in the kitchen towel, but I’d sort this out before marrying Chef Boyardee.

Jenny D. You’re right to proceed with care. How is he with money outside of his student loan debt? Do you hope to have children together? My guy and I have “money dates” once a month—where we talk about both the practical financial aspects of our life together and also, without criticism or judgment, our hopes and fears around our (and each other’s) money habits. They’ve been incredibly helpful! Maybe try one for yourselves and see what happens?

Hannah C. Marry someone who is interested in your financial security. He doesn’t have to be rich but he should be considerate.

I’m married, and have the hots for the husband of our very good couple friends (his wife is my best friend!). Because our young kids are the same ages and also best friends, we pretty much see them every weekend. I dream about him and even feel flushed and self conscious around him. I know I would never act on this attraction. I just want it to go away. How do I live with this feeling?

– Anonymous

Kara H. For what it’s worth, I don’t think that finding yourself attracted to a member of a close couple is unusual at all. I’ve seen it happen frequently—sometimes with the husband and sometimes with the wife. The key here is that you are clear that you are not interested in pursuing being a “friend with benefits” and want these feelings to ebb. You need to go on an elimination diet. Break the habit of seeing them for a month or two—you can see your best friend, your husband can see his pal, your kids can hang together, but put the kibosh on the family gatherings until your passion flashes recede.

Hillary R. Oof. This is a classic. It happens all the time. You need to remember that the grass always appears greener on someone else’s lawn. In reality, this guy is farting in bed, leaving his dirty socks on the couch, and refusing to replace the toilet paper, just like your husband. Or, as my beloved father once said, “Different face, same shit.” Step away and stay away. Not worth the devastation.

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Meet the Mods

Hillary R.

A recovering lawyer who has an opinion about almost everything.  And she’s usually right.


Dena G.

Over-the-top, wise-ass, soon-to-be retired school teacher who aspires to count beyond two breaths in her meditation practice.

Jenny D.

Rumi-loving real estate investor with passions for curiosity, stillness, surprise and good stories.

Kara 1

Kara H.

The brains behind the scenes, she balances edge with empathy. And appreciates a really good jumpsuit.

Hannah C.

Yoga instructor, life coach, and spiritual consiglieri to the rich and powerful. Her clients love her for her preternatural ability to shoot from the hip and from the heart.

The Woolfer
Woolfers, all women over 40, share a certain sensibility — a sense of humor, an appreciation of art and culture and literature, a desire to be candid, kind, self-reflective, and thoughtful — while also coming from a wide range of backgrounds and perspectives.