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AUTHOR: Mark Crothers on 3/10/2026

When I’m turning a tricky problem over in my mind, my normal port of call is my wife Suzie…she’s much more sensible than me. But I have an issue I can’t ask her thoughts on. The reason is simple — it’s a secret that she knows nothing about. So I thought I’d canvass opinions from the Humble Dollar community.

Right now I’m thinking of offering four separate loans to extended family members, and the backstory is straightforward. My wife Suzie turns 60 in late November. A WhatsApp group was set up to coordinate a secret overseas trip to celebrate together — flights, fancy accommodation, the works. Then, just before Christmas, our daughter announced her wedding. Suddenly the same group of people had two major overseas expenses landing within months of each other. For some of them, that’s one trip too many.

The majority of our secret WhatsApp group have suggested a solution is to push the birthday trip back six months. But here’s my thoughts — once the day passes, it’s a memory. You can’t go back and celebrate a 60th that came and went six months ago. So rather than reschedule it into irrelevance, I’m thinking of suggesting I cover everyone’s costs upfront and let them settle up when they can. They’ve all indicated that they would be in a better position for the trip in six months, so I feel repayment would be within that timeframe…give or take.

I’m not even going to call it a loan. The way I’m pitching it is simple — I’ll float the trip until everyone is in a better position. No pressure, no timeline. It sounds like a small distinction but I think it matters. A loan has weight to it. This is just family looking after family.

I trust them completely. That probably sounds like the thing every cautious friend warns you never to say. Maybe they’re right. But keeping everyone at the table and facilitating a family event feels worth more to me than protecting my wallet.

To me, I’d be ensuring a memorable 60th birthday for my wife Suzie with people we care about. What do you think? Am I making the cardinal sin by lending to family? Have you had bad or good experiences leading to loved ones to push a special event over the line?

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achnk53
18 days ago

There is no price tag(s) when it comes to family experiences and enjoyment with each other. I have also floated the idea with our family of 9 for an overseas trip maybe during Christmas. The memories you will have and shared are simply priceless. GO FOR IT as a gift of love and not a loan. If they want to repay that will be fine.

Jeff Bond
19 days ago

Mark – I’d say go ahead and do it. Call it a loan, call it an offer, call it a gift, whatever. Walk away from the celebration with the joy and happiness of having all of these important people in one place at the critical time. Then, be mentally prepared to never see some of that money ever again, because someone likely won’t pay you back. Keep a stiff upper lip whenever you see those folks again and remember what a great celebration you planned and executed.

Dan Smith
20 days ago

Okay, yes, I think covering the cost for your daughters, their partners, and the grands is plenty generous.

Grant Clifford
20 days ago

I am in agreement with most of the comments below. Here is my 2 cents.

My father (a proud Irishman) had a falling out with his siblings (also proud Irishmen and Irishwomen) over their parents’ estate. It wasn’t a large estate by any stretch of the imagination, but because their pride this disagreement kept them apart until they day they died. I am certain my late father shoulders more than his fair share of the blame for this. I have not seen my cousins in 40 years, which I hope to change this coming summer. The reason I mention this, money can cause rifts, even ones we don’t see coming. What if one child repays and another doesn’t, does this become a rift?

Assuming everyone has available vacation time, and you have the means, I suggest covering the cost of the trip equally for everyone, or as equitably as you can. Make it clear what you are and are not covering with your generosity and most importantly have a wonderful time creating memories with your family.

Grant Clifford
20 days ago
Reply to  Mark Crothers

I see the dilemma, 21 people really adds up!

R Quinn
20 days ago
Reply to  Mark Crothers

I think you understate that Mark. Cut the group size. 60 isn’t that big a deal anyway. 😎Tell them all to save up for 65.

Luvgov
20 days ago

Looking at the other comments I would be concerned that you are scheduling 2 big trips too close together. Especially for anyone attending that is still working. It’s not just about $$. It’s also about time off. If it were me and my husband had planned a special trip, 6 months before or after would not be a concern. I would just be super happy!

David Rhoades
20 days ago

My advice would be NOT to ever LOAN money to friends or family members because it is very likely that it will end up ruining your relationship with them. Since YOU want your friends and family to all celebrate your wife’s 60th birthday together, and apparently you can afford it, then I think it would be very magnanimous of you to offer to cover all of the trip costs.

Marilyn Lavin
20 days ago

If you’re SURE your wife would want the birthday celebration, then I’d say you should just cover the costs. No loans, just pay for it. But I’m wondering whether you may be shoehorning a lot of celebration in a very short time frame. Not to mention the Christmas and New Year’s holidays that fall between the birthday and wedding,

Marilyn Lavin
20 days ago
Reply to  Mark Crothers

Spoken like a true retiree!! A week is a lot of time for a working adult. I suggest that you skip the surprise and ask your wife what she thinks. The money seems like a minor issue.

Marilyn Lavin
19 days ago
Reply to  Mark Crothers

If your wife’s birthday is at the end of November, be careful about the expectation that she’ll want to stay on a few extra weeks. The months before a wedding tend to be filled with surprise “emergencies.” Also— the wedding should be the big deal; birthdays happen every year.

Howard Schwartz
20 days ago

When my wife loaned her cousin a lot of money so he could replace his home’s septic system, she drew up a note and also a letter with her expectations for repayment terms. He fulfilled the terms and they still have a relationship. If you do not formalize the loan with all the necessary paperwork, it is not really a loan, just an intension written on ice.

Dan Smith
20 days ago

Mark, it’s not possible for me to know about your family member’s financial situations. Thinking back to my younger self, I’m certain I would have signed on for the event, and I’m certain I would have had to borrow money to make such a trip necessary. 
Putting myself in your shoes, if possible, I would gift the whole kit and caboodle.

Last edited 20 days ago by Dan Smith
R Quinn
20 days ago

Forget the word and concept of lending. Suzie is your love, just pay for the trip. Let them push their funding back six months.

Postpone the whole trip and there will be other excuses later. Sounds like some folks had grand ideas but not the funds to back them up.

Humdude
20 days ago

I trusted my wife’s sister when we gave her a loan for 5K USD…until I didn’t. That money would have doubled twice since then. I am bitter. I could use the 20K today. My wife lost a sister because the sister can no longer face us after stealing the money. If you are going into this not ever expecting the money back thats fine. Also, have you considered some of these family members may be using the money factor as an excuse not to go? I admittedly do not know your family dynamics….good luck!

Last edited 20 days ago by Humdude
Chris G
20 days ago

Beyond the expenses of the trip, could there be a limited-time-away-from-their-jobs factor leading them to suggest postponing the birthday event for 6 months?
Or is the birthday just a weekend away? I ask because our younger family members do have time constraints and can’t schedule week-long, fun events the same way retirees can.

Randy Susan Treer
20 days ago

Agree w/Greg …”always consider a loan to a family member as a gift”

Michael1
20 days ago

I think your plan is great. I would absolutely do it. Never mind any advice about lending to family. I agree with Greg below, and you’re already not calling it a loan. Sounds to me like you’ve accepted that if it takes forever (or longer) to get it back, it’s all good. Also, it’s not for them, it’s for Suzie and you. Make it happen and enjoy.

greg_j_tomamichel
20 days ago

Mark, I commend your plan – go for it! But I also remember the advice I was given once – always consider a loan to a family member as a gift. If it does get repaid, that’s a bonus.

baldscreen
20 days ago

I agree with this. You have a generous heart, Mark. Chris

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