Matt Cardillo's parents were nearing retirement, and he didn't have a clue about their plans. He was only in his early 30s, but with a son on the way and a mortgage to pay, he couldn't help being concerned about their future financial stability.

His predicament: how to raise that question with the very people who taught him how to plan and save.

“Talk about the awkwardness of it,” said Cardillo, a software consultant from Gaithersburg , Md. “As soon as you go there with the discussion, they're thinking the extreme: Lock me away in a nursing home.”

Issues associated with the later years in life -- retirement savings, long-term care, inheritance -- can be difficult subjects that neither aging parents nor their middle-aged children want to confront. But financial experts emphasize that it's in the interest of both generations to talk about long-term financial questions before a crisis hits.

That conversation, however, carries heavy emotional weight, foreshadowing a reversal of roles between parent and child and tangling the fabric of family relations.

Strategies for handling the conversation vary as widely as family styles, according to psychologists and financial experts. Some parents and their children can openly discuss many issues, including finances, while other families may need prodding to get the conversation going. Some parents, out of pride -- or even suspicion of their children's motives -- may avoid the topic altogether.

``There's the whole issue of making people talk about death and dying... and money,'' said Olivia Mellan, a psychotherapist and author of Money Harmony, which deals with the intersection of relationships and finances. ``These are two loaded issues. And together, it's a heavy thing.''

Cardillo's first attempt to bring up the subject of money with his mother came as his parents were moving from one Tampa suburb to another three years ago. Cardillo and his brother went to help with some electrical and carpentry repairs at the new house.

As they were working, Cardillo asked his mother, Julia, whether she had thought about long-term-care insurance to pay for nursing care or assisted living later in life.

``I looked at him and said, `Well, a little, but we don't know much about it,' '' recalled Julia Cardillo, who was 61 at the time. ``I said, `Could we talk about this tomorrow?' ''

Matt Cardillo had been thinking about long-term-care insurance after reading an article about the escalating costs of nursing-home care. He knew that long-life genes ran in his family -- one of his grandmothers lived to 98.

Cardillo continued to press his point, bringing it up on the phone, sending relevant newspaper articles, but without any progress. The insurance seemed too expensive, his mother kept saying.

Cardillo then set out on his own to buy a long-term-care policy for his parents. He enlisted the help of his financial planner, Tom Curtis of Gaithersburg, Md., who narrowed the options and prepared the paperwork for a policy. When his mother came to visit after his son was born in fall 2004, Cardillo told her they had an appointment with his financial planner.

Once they got to the meeting, her resistance disappeared. Curtis presented various options on long-term-care policies and gave some additional advice on how Cardillo's parents could improve their finances.

At the end of the meeting, Cardillo signed a check for the down payment on his parents' policy, and Julia Cardillo took the paperwork home to Florida for review. His parents then started paying the premiums on the policy, which covers them for the rest of their lives and provides nearly $37,000 a year for long-term-care expenses.

``I was really proud he brought it up,'' said Julia Cardillo, now 64. ``It was an act of love.''

The question Cardillo raised with his parents about long-term-care insurance points to a fundamental concern for families. Financial experts say that as the baby-boom generation ages and medical costs continue to rise, a greater portion of parents' medical expenses might fall on their children's shoulders.

Spending on long-term care, for example, is expected to almost double by 2020, to $207 billion from $123 billion in 2000, according to a report last year by the White House Conference on Aging. The report also said that more than one-third of Americans older than 65 will spend at least some time in a nursing home, with half of that group spending more than a year there.

But Medicare, the government program for the elderly and disabled, covers nursing-home expenses only in rare cases. And eligibility rules for Medicaid, the government medical program for the poor, have been tightened to make it tougher for middle- and upper-class people to divest their assets to qualify.

Only 6 percent of Americans buy long-term-care insurance -- many, such as Julia Cardillo, are deterred initially by the price.

But rising medical costs, a population shift and regulatory changes may force more people to add long-term-care coverage and other financial protections to their portfolios, financial planners say, making that family conversation more important than ever.

``To ignore it and bury it, which happens more often than not, you're just looking for more problems down the line,'' said Arthur Stein, a financial planner in Bethesda, Md.

Opening a line of communication might be the biggest challenge. Financial experts recommend taking advantage of moments when parents bring up the subject of retirement on their own. Trying to open the conversation with, ``Mom and Dad, you're getting older... '' is usually a dead-end.

Families also need to consider timing. Depending on family dynamics, the holidays can either be a great time to talk or a terrible one. If possible, the subject should be brought up in person rather than over the phone, financial planners say.

Whatever the situation, experts say it's important to keep the dialogue rational and money-focused. Financial experts recommend that the children have their own houses in order before they start poking into their parents' accounts.

All siblings should participate in the conversation and be on the same page about the strategy. And the approach should be inclusive, by talking about how ``we'' can sort out the financial issues.

From there, it depends on the individual situation. Early on, determine whether there is a will, define power of attorney for any financial or legal documents, and set up medical directives that spell out the circumstances in which a parent would want to die.

Those topics can often be harder for the younger generation than their parents.

``What's lurking in the background of these conversations is, `Someday my mom and dad are going to be old and frail, and they're going to die,' '' said Brian Carpenter, an assistant professor of psychology at Washington University in St. Louis who studies what middle-aged children know about their parents.

If family members resist having a conversation about long-term finances, financial experts say, it might help to have a third party such as a lawyer or financial planner participate.

``What I often say is, `Use me as an excuse,' '' said Steven Wertime, a financial planner with Wertime Financial Services in Falls Church, Va. ``I can defuse the emotional issue.''