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A recent study of online dating websites found that women find men most attractive at 50, and men find women most attractive when they are 18.

This doesn’t seem shocking to me. Prior to focusing my practice on asset protection, I practiced probate litigation. I can rattle off a string of cases involving romances between younger women and older men. However, I can’t recall a single case involving the reverse (of an older woman and a younger man).

In my experience, the romance typically begins when a female caretaker or a next-door-neighbor starts to help out an older male bachelor. Older men are often lonely and crave the extra attention (especially from an attractive younger lady friend). So, it seems like a perfect fit. Except that they aren’t the only people interested in the outcome of this scenario. The man often has children from an earlier marriage. And they expect to inherit their father’s money.

This makes for strange dynamics. The romance is sometimes concealed from the other family members, to avoid any conflict. Otherwise, the romantic relationship with the younger lady strains the man’s relationship with his kids. The kids can become estranged to their father. Even though he loves his children, he also wants romance.

Amid all of this, the man often changes his estate planning documents to give some or all his wealth to his caretaker-lover. If the kids find out about this during their dad’s lifetime, one of them can go to court and seek to be appointed to make personal and financial decisions for him. The father may fight this, because he wants to have a girlfriend.

Alternatively, the fight might not happen until after the father has died. Suddenly the kids sue the girlfriend, claiming that she pressured their dad to change his estate documents, so she could inherit from him.

Either way, all sides can end up spending fortunes in legal fees fighting each other. The saddest scenario is when this happens during the father’s lifetime, and the lawyers end up eating through the bulk of his wealth in the course of litigation.

The solution is not to simply have updated estate planning documents. This may help ensure success during a court battle. But it does not actually prevent the court battle.

So, what’s the solution? How can an older man protect himself from such squabbles?

The answer is to take the cards off the table. Make it impossible to get embroiled in a legal mess. Here’s a short checklist of things for a man to do before getting into a relationship with a younger woman.

  1. Create an offshore asset protection trust. I prefer to use a Nevis trust company, because Nevis has a strong statute and their trust companies charge less than their counterparts in (for example) the Cook Islands.
  2. To provide further protection, form an offshore LLC in (for example) Belize that will actually hold the cash or investments. This LLC is 100% owned by the asset protection trust. The manager can be the man. Result: The man’s assets are outside the jurisdiction of the U.S. courts, but still in his control. The LLC’s operating agreement needs to include protective language so that if someone tries to pressure the man to change the estate plan, a neutral person (such as the man’s lawyer) needs to consent.
  3. The man needs to have a really good relationship with a lawyer or CPA who can serve as the neutral person to consent to any changes. In the context of the trust, this person is called a Trust Protector. This neutral person serves a crucial role in ensuring that the man’s ultimate estate plan doesn’t get changed later.
  4. The offshore asset protection trust then has the option of “pouring” into the man’s U.S.-based revocable trust upon his death. But the trust protector’s consent is needed. Remember that the trust protector is either the man’s close lawyer or CPA and is familiar with the man’s ultimate wishes. So, if a family member or girlfriend pressures the man to change his trust and give everything to one child or to the girlfriend, the Trust Protector can correct course and instruct the asset protection trust to distribute the funds as the man historically would have wanted.

This solution makes the most sense financially for a man with at least a couple million in net worth. However, I’ve seen people with less than that lose their life savings from court battles. So, there is no magic number at which this solution makes sense. It really depends on each person’s situation.

Compared to the alternative of having a family torn apart by years of court litigation, this is a much more elegant solution.