Legal Question in Civil Litigation in Massachusetts

It is usually better to proactively take charge of these quasi love/loan transactions as soon as possible. Prolonging a complete settlement only provides an excuse for him to still be in contact with her (I assume that she is through with this relationship and wishes to move on.)

This unwanted contact between this young man and your daughter (which you refer to as "stalking", is very serious. The crime of "stalking" is a serious felony in most jurisdictions and carries potent criminal sactions. Such a charge can severely destroy a person's reputation and career.)

You might propose a written payment plan with realistic terms of repayment. Both he and your daughter should agree to the terms and sign it. Having achieved this written understanding, your daughter should follow through and make payments as agreed.

If you need to, be sure and seek further legal assistance before both of these youg people incur unwanted legal consequences from their prior relationship.

Good Luck!

If she regarded the money he paid as a gift, she should do nothing that is inconsistent with that. IF she wants to pay him back (i.e., return the gift) she should make sure, when she is communicating with him, that she makes clear that she regards it as a gift and that, while she intends to return the money, she does not believe that she has any legal obligation to do so. She may want to state this in writing; acknowleding the money he put up, explaining how she regarded it as a gift, and making clear that, while she feels like she has no legal obligation to return the money, she intends to when she can afford it and that no payment be her should be regarded as any admission of any legal liablity.

I am much more in agreement with Attorney Harrimgton than Attorney Wood on this issue. Unfortunately, these kinds of situations are all too common, and the key issue always comes down to whether the money given was a loan or a gift. As you've already surmised, there is a legal obligation to repay a loan, but no such obligation to "repay" a gift, so the distinction is very important in figuring out this issue. One would think that a smart young man who also works for an attorney would know enough to have your daughter sign a promissory note or some other written document to demonstrate that the money was given as a loan. That he did not would seem to hurt his case considerably, unless there is some other evidence to show that the money was given as a loan. In any event, assuming your daughter is willing to repay this person, I think the approach suggested by Attorney Harrington protects her interests much better. Moreover, it doesn't require that she enter into a settlement agreement with her ex. If something were to go awry with her repayment plans, a signed settlement agreement would give him an entirely independent basis to go after her for the money, and may actually turn a losing case for him into a winning case, because he could simply seek to enforce the new agreement, rather than have the court determine if the original arrangement was a loan or a gift.