Dear Mrs. Riches:
I have a dear friend, Mrs. S, who is a charming widower in her late 60s. In the time since her husband's death a year ago, another man has entered her life. He is slightly younger, very active, and attractive. Mrs. S., who had a very hard time during her husband's decline due to cancer, has blossomed since beginning to see this man. She seems happy and re-energized about life. Terrific, right?

But Mrs. Riches, I smell a rat. He seems to be trying to limit her contact with old friends. He doesn't seem to have his own job but talks about "deals" and "plans" and things that are "sure to pan out." In a moment of confidence, she told me that he is already talking about marriage. I just get a bad feeling about this and think he is after her money.

I don't want to tarnish my friend's happiness, especially after all she has been through, but I also don't think I should just let him take advantage of her. Is there any way I can help her protect her assets? Please share an outsider's point of view.
-- Rat-Detector

Dear Rat-Detector:
This is, indeed, one of life's dilemmas: How do you save loved ones from themselves, let alone from someone with ill intent?

In the case of Mrs. S., she is particularly vulnerable following the death of her husband. That someone finds her interesting and attractive probably feels very good at this point. As you say, it is hard to imagine dashing all those hopes, just as she is rekindling some joy in living.

But at the same time, you mistrust this man who has made Mrs. S. blush, smile, and begin to have fun again. And things could go wrong, terribly wrong, should he prove to be the rat you think he is. Mrs. S. would surely be devastated emotionally and may end up losing a pretty penny in the process -- neither of which is an acceptable risk for a caring friend.

At this point, it sounds like you are simply going on intuition, aided by this fellow's discourse on all of his ships that are going to come in. While I'm a firm believer in following your gut (except to the ice cream aisle), I also think that these are large doubts that have a better chance of being believed if there's some evidence to back them up. People in the throes of a new affair of the heart tend to let down their defenses but dislike it intensely when others point that out. They don't call it "crazy in love" by accident! Should you choose to confront the issue head-on with your friend by sharing your concerns, you'd best have some more proof. Otherwise, you may simply alienate her and lose your chance to make a positive difference.

In the absence of that, I'd try to approach the issue with Mrs. S. through less potentially volatile channels. How?

  • Continue to offer Mrs. S your friendship and support by calling, emailing, and making time to spend with her.

  • Give her books about the grieving process, the loss of a spouse, and moving on. Many of these types of books discuss the need to fully grieve before making major life decisions like relocating or remarrying.

  • Encourage Mrs. S. to see a financial advisor to help her take care of her estate. Having a professional advising her about her assets may help to put safeguards in place.

  • If Mrs. S has any children, you can talk with her about the need to protect their interests. Their father, now deceased, would surely have wanted to make sure they would be taken care of, whether that's accomplished through a prenuptial agreement, trusts with the children as beneficiaries, or, at the very least, by documenting what possessions and monies belong to Mrs. S. before she enters into a new marriage.

If you're interested in hearing more from Mrs. Riches, try:

Fool contributor Elizabeth Brokamp is a licensed professional counselor who regularly talks money with her honey, Robert Brokamp, editor of the Motley Fool Rule Your Retirement newsletter. To get your money and relationship questions answered, send her an email .