Dear Helaine: My boyfriend of four years wants to get married and I'm hesitant. Part of it is that I'm in my late 40s, been married before and got taken in my divorce.

My ex had wealthy parents, and we were going to inherit one day, so we used my money for extra expenses like the down payment on our home and travel. I also took out the max in student loans because we figured we could pay them off when we inherited. Instead, we got divorced, and I ended up with my original down payment and all the student debt. Of course, this soured me on marriage.

So, my boyfriend. I earn $30,000 a year more than him, and I save diligently. He spends without thinking, doesn't plan for the future, and has no retirement or other savings. Neither of us has any debt, but I worry about combining money when our approach to finances differs so, and, of course, I worry about the financial impact of another divorce. So I've said no to marriage, but I know he still really wants to.

I would love some advice on how to approach our differences. Does it make any sense to be in a relationship with someone whose values around money are so different? -- Once Burned

Dear Once Burned: You learned the hard lesson that funds are not your funds until they are in your bank account. You've now taken that lesson to heart -- maybe too much to heart. So here is my two cents: No two people are ever going to agree in full about how to approach their finances. Your wannabe husband isn't so much irresponsible with money -- as you point out, he doesn't have debt -- as he's not fully an adult about how to approach it. It's a subtle distinction, but an important one. It means there is hope you can work this out.

You are most certainly not out of line to say you would not marry him without evidence he can save money, and do so for a period of time. Perhaps give him some guidelines, such as, "I would like to see you contribute 5 percent of your salary for a year to a 401(k) before I consider marriage."

But that's IF you want to marry again. There's no reason to do so simply because he would prefer it. You need to want it as well. And there I can't help you. Only you can answer that question.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Dear Helaine: My fiance and I are 27, debt-free and combined earn $150,000. We also live in a city with a high cost of living and rents. We both think it would be great to have our monthly payment going toward something we can own when our lease is up this summer. However, we only have $10,000 saved specifically for a down payment.

Up to this point, we've been paying off what debt we had, dealing with an emergency, saving for retirement, building a six-month emergency fund. My parents are paying for the wedding. What is it OK to cut or put aside so we can come up with at least a 10 percent down payment? Can we skip a year of retirement savings? Cut down our six-month emergency fund to a three-month fund? Sell off investments we have outside of our joint housing savings and retirement accounts to fund this?

I intend for the first expense post-house to be replenishing whatever funds went to the down payment and paying down the mortgage, so we can eliminate the mortgage insurance ASAP. Is it ever OK when you are earning a lot to temporarily cut back on your financial safety net? We have the money, just not right now. -- Homeowner in Waiting

Dear Homeowner in Waiting: Here's one easy way to buttress your house savings fund: downsize the wedding and ask your parents if they'll put the saved funds toward your future housing fund, either in the form of a gift now or an assist when you've found your home. A wedding, as meaningful as it is, is one day in your life. A home you will live in for years to come. I suspect it's a rare parent who will say no to such a request. (I'm assuming your parents have the money, and aren't charging the shindig on a credit card.)

That being said, I'm guessing, based on your comments, you'll need at least $50,000 to come up with a 10 percent down payment. Your habits seem good, and I would suggest cutting back to a three-month emergency fund and tapping into your individual investments held outside of retirement accounts before downsizing or eliminating saving for retirement.

One other thing: Make sure you can afford to own a home. In many cities, especially high-cost ones, it is cheaper to rent than own when all the added costs (property taxes, high cost of buying, home maintenance and so on) are added in. I would hate to see you get financially ahead of your skis as you begin your marriage. On that note -- congratulations!

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Dear Helaine: I'm a 55-year-old woman living in New York City. I'm recently divorced and received a $100,000 tax-free settlement. Before the divorce, I lived in a nearby state.

There's no alimony. (We earn similar amounts of money.) I'm a contract worker, and I am responsible for setting aside estimated taxes. I don't receive benefits. I have about $15,000 in an Individual Retirement Account and live paycheck to paycheck on a $50,000 salary. That's half of what I earned prior to the 2008 economic crash. I also don't own a house; I am paying $1,100 a month in rent, and that's with taking in a roommate.

I want to invest as much of that $100,000 as I can, but I am concerned about my tax bill and living in a new state, and I am worried about health insurance costs too. What portion should be SEP IRA, Roth or regular IRA, and what other kinds of investments. Stocks? Bonds? I do not have a clue. -- On My Own

Dear On My Own: I'm not going to sugarcoat this. You are in a very precarious financial situation. You are way behind on your retirement savings, you don't own a home, and you are reaching an age where age discrimination becomes extremely common. The long-term consequences can be severe: According to research, 25 percent of women who divorce after the age of 50 end up living in poverty in retirement.

So what to do to prevent that fate? You don't say if you have any emergency savings -- that is three to six months essential living expenses set aside, something that's even more important given you are a contract worker. You need to put that sum in a money market fund if you have not yet done so and then forget it.

After that, you need to seriously consider looking for employment -- as in the employment that comes with benefits -- if you want to remain in an expensive, high-tax metropolitan area like New York City. If you don't want to do that, or do not believe you can get a full-time job with benefits, you might need to consider relocating to a less-expensive region of the country.

Finally, as for the investment angle, you can't just put all of your divorce settlement in an IRA, Roth IRA or SEP IRA; there are annual limits on that. I suggest picking up a copy of the book I wrote with Harold Pollack: "The Index Card: Why Personal Finance Doesn't Have to Be Complicated." That will help you with retirement savings strategies as well as tell you how to seek out professional advice that will be in your best interests.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)