Besides masseurs and escorts, what’s the highest amount of money that you don't regret spending?

[+ 7829V]

Giving my parents 25K cash for a mortgage down payment in my home country.

[+ bashful]

I actually don't know the exact amount, but it was a bit north of seven or eight grand at the Four Seasons in Maui (not counting airfare). Twice.

[+ harey]

Giving my parents 25K cash for a mortgage down payment in my home country.

Wonderful to give back that way. (And I’ll be your daddy for that kind of money)

[+ keroscenefire]

I definitely do not regret spending money on travel. I am not really a "luxe" traveler so for me the money is spent on the plane tickets themselves. The only thing I regret is not having travelled more.

[BSR]

I definitely do not regret spending money on travel. I am not really a "luxe" traveler so for me the money is spent on the plane tickets themselves. The only thing I regret is not having travelled more.

Despite not making that much in my 20s, I managed to take 8 trips to Europe, a trip to Australia & AZ, and live in Spain for a year. I traveled on a shoestring, even slept rough a few nights, but at least I had the experiences. I wouldn't trade those experiences for the world.

[+ keroscenefire]

Despite not making that much in my 20s, I managed to take 8 trips to Europe, a trip to Australia & AZ, and live in Spain for a year. I traveled on a shoestring, even slept rough a few nights, but at least I had the experiences. I wouldn't trade those experiences for the world.

 

Yeah I travelled a bit in college but once I got out it was the last recession and I was hit pretty hard by it so ended up pretty broke for a good half-decade at least. I did manage to travel some in the US though so that was wonderful.

 

Now that I am back in a more stable career though, I have the wonderlust real bad and can't wait to get out and travel some more.

[+ MysticMenace]

Giving my parents 25K cash for a mortgage down payment in my home country.

 

Certainly not loaded like @7829V, but it definitely made me happy paying the entire trip for my parents when they went back to the Philippines after not having been back in 18 years. First-class flights, combo of luxury hotels and resorts and AirBnB for their 2-month stay, and $10K pocket money to treat my relatives on my mom's side of the family during their trip. Everyone seemed to have a fantastic time, so it made my heart melt. Certainly no luxury international travel for me that year, but definitely no regrets on giving my parents the time of their life.

[+ WilliamM]

Despite not making that much in my 20s, I managed to take 8 trips to Europe, a trip to Australia & AZ, and live in Spain for a year. I traveled on a shoestring, even slept rough a few nights, but at least I had the experiences. I wouldn't trade those experiences for the world.

 

Interesting and fun. In my 20s, a friend paid back a moderate size debt. I used the money to fly to Rio and Brasilia in 1974. Had always traveled with other people before, so major learning experience.

 

To write Brasilia was in the middle of nowhere would be an understatement.

[Luv2play]

Giving to charity. I give around 8 percent of my annual income (after tax) to local charities and organizations that have meant a lot to me in the past. Have been doing this for the last 10 years. The rewarding part is being involved with these charities and helping to guide them as a member of their boards of directors.

[dbar123]

Spent $10K on a custom build titanium bike. Seemed ridiculous at the time but when I ride it- no regrets at all

[Lchnsf]

Bikes: $9000 for a custom Ti road bike

$25,000 for a Carbon Race Bike

$8,000 for a gravel bike

they all continue to bring me joy.

[+ Coolwave35]

$150,000 to a charity so they could purchase a commercial building.