How to gift your child wedding money when you don't trust their choice of spouse

From a recent Ethicist:

My wife and I have two adult daughters. They are very close in age and deeply connected to each other (thankfully). They attended private school and graduated from private colleges, without college debt, as we paid for everything. They are both really good people, and we are very proud of them.

Years ago, my wife and I agreed we would provide a fixed sum for our daughters’ weddings when the time came. (They could each decide how to spend it — on the ceremony, the honeymoon, a down payment on a house or whatever.) We decided to do this for a few reasons. We don’t see the value of a large and elaborate wedding. We gifted our children a superior education. And we wanted to avoid having either daughter complain that we spent more money on one wedding than the other or any last-minute requests for more money to upgrade the ceremony.

One of our daughters recently got married. We provided the gift money as promised (a not-shabby five figures), and it went toward a fairly fancy and large wedding.

Our other daughter isn’t in a serious relationship at this time. However, she has demonstrated some poor judgment in trusting people who have not earned her trust, and this makes me concerned about whom she might choose to marry.

Which brings me to my question: Are we obligated to gift the money as promised if we have a serious issue with the character of a future fiancé — his personal history, lack of a career path or ability to maintain steady employment? Our concerns would be based on her welfare, not on whether we “liked” the guy.

Another option: Would it be acceptable to place conditions on the gift? Or gift it in another fashion, such as a college savings account for future children? Something that would not go to waste or be divided in a messy divorce.

If we did any of that, we would be indicating that we are not in favor of this wedding and do not want to contribute toward it. But we would and will provide equal financial support in the future under certain circumstances. I hope this scenario won’t happen, but I do wonder what the proper and fair approach might be or if it is necessary to worry about “fairness.” Name Withheld

There's a simple way to reduce the risk of the the money being wasted on a partner of poor character while also avoiding treating your daughter unfairly or in a way she'd find alienating: give her the money now.

If she has the money now, while she's not in a relationship, she's far more likely to use it to benefit herself, towards a downpayment on a home or further education or to start her own business - or, yes, to put in a wedding fund, which would also double as emergency savings until such time as a wedding is imminent.

Divorce law varies by jurisdiction, but a general trend is that assets brought into a marriage are less likely to get divided during a divorce than assets acquired during the marriage. Prenuptial agreements can also reduce the likelihood of these assets getting divided. (As ever, people should consult with a family lawyer about their actual situation.)

Messaging is important here. It can be difficult to be the only unmarried person in your family, and you want to avoid presenting this to your daughter in a way that might hint at either "You are a person who chooses bad relationships!" or "You are a person who will never get married!"

This is where the pandemic comes in handy!

The pandemic has shed light on the many ways previously-unquestioned practices don't serve everyone well, and has led many people to rethink a lot of things they previously took for granted. 

You can use this to construct a narrative where the pandemic has made you rethink tying this financial gift to getting married.

Example: "We were recently [thinking/talking/reading an article] about how the pandemic has hindered dating and developing new relationships, and what kind of impacts this might have in the medium and long term. And we were also [thinking/talking/reading] about how the pandemic has driven up housing costs and generally made life more difficult for people just starting out, and what kinds of impacts this might have in the medium and long term. And we realized that it's hideously old-fashioned and completely unfair to tie the gift money to getting married. Therefore, we are going to give it to you now, so that you are empowered to use it to get started out in life according to your own best judgment, without having to wait for some arbitrary milestone, with our apologies for making you wait this long."

Basically, approach it from a position of humbly correcting a flaw in your own previous policies, without any mention whatosever of your evaluation of your daughter or her future spouse.

This is proper and fair, deprives your daughter of nothing, maximizes her opportunities to benefit from the money herself without being influenced by a questionable spouse, and keeps your relationship with her as positive and judgement-free as it has ever been.