Was just wondering what your worst-ever use of miles for a ticket was?

I booked a r/t ticket for me and a 1-way ticket for my 4 y.o. daughter PHL-MCO later this month so that I could take my daughter to my sister's where she will visit for about 12 days. I fly back by myself several days later. Didn't initially book wifey b/c of the cost. Now that we are getting close to the trip, my wife is concerned that 2 weeks will be a long time away from our daughter. So, thought of getting an award ticket on US. Best I could do is 25,000 miles down and 12,500 miles return. US will charge $80 for the ticket...$50 for being less than 14 days (or whatever their cutoff is), then $5 for something, and $25 for something else. I would also need to purchase another 1,000 miles (actually only need 491) at a cost of $25. So basically my cost is $105 plus 37,500 for a $295 ticket (getting wifey on the same flight on which my daughter and I are already booked). Normally, I would just buy the $295 ticket, but money is tight right now so thinking of spending the miles and $105 to get my wife on the flight.

The other factor, which can't exactly be measured in monetary terms, is that we have, through my brother-in-law who works at Disney, free access to Magic Kingdom/Epcot/etc. Our daugther is at a perfect age for a trip to the "Magic Kingdom" which would be a lot of fun; but I wouldn't want to take her there myself without my wife. So, there is "value" of sorts in having us all make the trip to Orlando.

So, basically I'm using 37,500 miles to cover $195 worth of ticket; I know! Terribly inefficient use of miles!

So, what is YOUR terribly inefficient use of miles story?

Cheers,
HalfSwede