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One suggestion that may make financial sense, but that’ll probably make for a seriously uncomfortable conversation around the dinner table, will begin with you asking: “Hey dad, I was thinking of taking a life insurance policy on you. When do you think you’ll die?”

5 crazy money ideas that just might work. To the right individual in the right circumstances, buying a vacation home, opening an extra credit card account, or overpaying the IRS can make sense. Well, some sense anyway. So can taking a life insurance policy on your parents:

After maxing out his Roth IRA, [Howard Bailey Financial VP Casey] Weade decided to take out a life insurance policy on his father. Then, when his father dies, he will collect the payout. Weade acknowledges this strategy will sound morbid to some, but he insists that it makes sense. “He’s in really good health at 61, and I’m 25. In 30 years, I’ll be 55 and he’ll be over 90, and there’s a low chance of living that long, so I’ll get that tax-free benefit by age 55,” he explains.

6 ways to shave the cost of having a pet. Consumer Reports recommends shopping around for flea and tick protection:

CR found two that were new to the market, SentryFiproGuard Plus at Petco and PetArmor Plus at Walmart. The savings can be sizable. PetArmor Plus was the best deal CR saw: A three-month supply cost $28, compared with $50 for FiproGuard Plus and $62 for Frontline Plus at Petco.

6 lessons learned from the recession. Seems odd that we needed a global economic collapse to learn basics like that the importance of setting budget priorities, building an emergency fund, and monitoring one’s investments. In any event, let’s hope that over the past few years you came to new appreciation for wisdom such as:

Being a penny-pincher makes you smart, not cheap

Deals abound as retailers and venues continue to compete for precious consumer dollars. Be aggressive about searching for discounts, and don’t pay full price if you can help it.

7 spending sins that will put you in debt. Ignoring any of the lessons above will do the trick. So can something referred to as “Disney Parent Syndrome” by divorce planner Gabrielle Clemens:

“My number one worry when I see newly divorced parents is emotional spending,” she says. “If they have children, there’s a lot of guilt. The dad who’s left the house becomes Vacation Dad or Disney Dad, or moms try to overindulge their kids. It’s emotional impulse spending that can lead people to problems with debt—improper debt.”

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7 ways to make your commute fun and productive. Your definitions of “fun” and “productive” may be a lot different than the commuters weighing in with tips, like:

“I like to pass the time [on the train] by writing haikus. The 5-7-5 syllabic structure is simple enough to allow for the quick generation of ideas. It also improves my observational skills as I turn the world outside my window into ‘art.’ A recent example: What is that creature? Woodchuck? Beaver? Groundhog? Mole? The world is his cube.”–Michael Y. Brenner, Ed.D., Jeffersonville, PA

9 insider tricks to outlet store shopping. Likewise, your definition of “outlet” and “outlet prices” may be different than the stores that call themselves outlets:

Check The Quality

Not all merchants sell the same products at their outlets as their retail stores. The prices may be lower, but you’ll sometimes find the quality is equally low. Watch for irregulars, different manufacturers, and bait-and-switch tactics.

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10 things shopping malls won’t tell you. Many malls are putting an emphasis on restaurants and food—not because they’re highly profitable, but because if there’s decent food (or any food) at the mall, that’s one less excuse a shopper has to leave. After fueling up, shoppers can shop some more. Also, interestingly enough:

There’s another reason malls are devoting more space and money to their food courts. Shoppers spend almost 20% more at a mall with a “good food court,” according to a 2007 survey cited by Sharma. And good, medium or otherwise, shoppers overall are spending more money on food at the mall, according to the International Council of Shopping Center.

10 cheap date ideas she’ll actually love. There’s a difference between a straight-up cheap date—Slim Jims, six pack, Cubs game on TV—and a wonderfully romantic one that happens to not involve spending a ton of money. Here’s a great suggestion:

Farmer’s Market in the Morning, Making Dinner Together That Evening

Staying in and making dinner together is as romantic as it gets, but use your dinner date as an excuse to hit your local farmer’s market that morning. Stroll past the different vendors, and eventually you’ll start assembling a pile of fresh local ingredients that you can use that evening.

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Brad Tuttle is a reporter at TIME. Find him on Twitter at @bradrtuttle. You can also continue the discussion on TIME’s Facebook page and on Twitter at @TIME.