Does anyone know how I can get a self addressed envelope and letter sent from Rome, Italy to my home in US for a bet?

I will tell you, if you tell how you got a taxi to take you 100 miles for free.
JK
That one is super easy. Send your SASE inside a mailer with a note, requesting that the recipient post it for you. Address the mailer to whatever they call the post office honcho in Rome.
Maybe include ten bucks, yunno.

go to the nearest international airport, and stand near the checkin counter for the next flight to Rome.

Ask the people in line – will you mail this when you get to your destination?

Someone will say yes.

@elbanditoroso, that sounds like a good way to get arrested. Security is pretty adamant about not taking stuff from strangers onto a flight, and there is lots of security near check-in points.

Do you Geocache? Geocachers will do almost anything for another cacher. Look up some caches in Italy and find a few in Rome. Look at who placed them. Then email that person. If you ask 2 people odds are really good at least one will do it for you.

I worked on a cache called something like “First to Find” It had clues hidden in boxes placed in different states around the country. The trick was to find and convince other cachers to find the boxes in their area and send you the clues. It was really fun and a neat way to make friends.

I got the taxi to drive me 100 miles for free by finding someone at the airport that had missed their connecting flight and my husband said ” if I give you the money may my wife ride with you to the airport where you can catch your flight?” We had already found out how much it would cost and knowing it was faster to get there by driving rather than waiting it worked.

Getting arrested in not in my immediate plans and asking a total stranger to carry even an envelope is a dangerous proposition these days, so I will skip that option.

I think that unless you travel to Rome on your own and mail the letter, you aren’t going to get a letter from yourself.
Mailing a letter and hiding the origins of it or faking things via mail might be considered mail fraud. And that would get you arrested. I can’t think of a legal way to mail yourself a letter from a different country.
If you paid the person in advance, that’s not really getting a free taxi ride

I got the taxi to drive me 100 miles for free by finding someone at the airport that had missed their connecting flight and my husband said ”if I give you the money”…

Free?

When I was in elementary school we did a project where we sent self-addressed stamped envelops to the postmasters of towns with the names of planets. We collected the cancellation marks and made a poster.

(I did Jupiter Florida.)

Send the letter in an envelope to a stranger in Rome and ask that they send to back to you. They will have to put Italian postage on it, so perhaps just put in a small pin or piece of American kitch as a thank you. Do this to a sample of 10 or 20 people and then wait. You might get more than one back, even. The addresses of hotels and other travel places would be the easiest to find addresses and contacts for and send to. You could also try home-stay places or those couch surfing places or Bed and Breakfast places.

Are you on FB? Why not put it out there and see if one of your friends has a contact in Italy.

Also, there is a Jelly who lives in Rome who is not very active. I’ll send this question to them and they can respond if they want to.

I am not on facebook so thank-you and the rules of the bet are that I have until March 25 and as long as I do not purposely alter a situation or do harm obviously, I can try any good method. It is to prove that there are still people who will help you whether you know them or have anything to gain from them or not. The free taxi was to S.F. to prove that 30 random people in 30 separate places in the city from all walks of life would say “I love you.” My uncle suffers from extreme depression and takes meds but has really bad times and goes off of them. If I win the bet he has to stay on them for 1000 days to prove they will help.

You are kind of altering your story so I am confused. At first, you said you had to have a free taxi, then you say you paid money. In your description you talked about getting paid 1000$ now you say your uncle has to stay on meds for 1000 days.
Out of curiosity, how does getting a letter mailed from Rome addressed from you proving that there are good people?
Are you able to travel to Rome yourself and mail the letter?

My husband and I do not combine our finances he asked to pay for the taxi. My Uncle will pay me $1000 to see if I fulfill the bet, if I do he will take his meds for 1000 days. Anti depressants take 6–8 weeks to get into your system before they really start working. The contents of the letter are private and he thinks that someone will open it rather then just send back the unopened sase inside, that is all.

No, I am not able to travel to Rome and that would go against my altering the rules of the bet. Thank you for your help, everyone has been great.

Huh? You just need to have a letter sent to you from Rome? Just get an accomplice in Rome to agree to mail you the letter if you send it to them. (If there’s a time limit and you’re really going to get paid $1000, use fast reliable mail such as FedEx.)

You can find accomplices in Rome at Internet cafes, Italian chat channels #Roma on IRC, for example, or just using Rome’s Craigslist page.