My first trip out of the US as an "adult" was to Tijuana Mexico. Not sure if we gained anything culture wise but I learned to not buy anything from the lady with 60 kids all selling Chicle.
Did my being in the military have any influence? Sure the heck did. The Navy & Marines had a curfew way back then and the Army didn't, we would stay and party till the wee hours at the Bambi club, Tilly's on 5th Ave, and on one occassion the El Zorro club until someone CS'd it after getting ripped off. Many a days down there we came stubling through the turnstyles at 0400. Hell once we even snuck a dog through!
I went back a few years after I got out and it was stil the same. A border town full of drunk sailors and soldiers all trying to pick up the underage college girls from SDSU.
Last summer we hit Nuevo Progresso Mexico. While it is a small border town it is a lot more rundown then TJ. The town on the US side is mostly winter Texans and they all head into Mexico to buy their prescriptions. You could not throw a rock without hitting a damned pharmacy or a dentist office.
Only thing I learned that time was not to eat any unpasteurized cheese. We had breakfast at a restaurant that my father in law liked. I ordered some eggs with queso blanco which I normally love except in the US it is pasteurized and does not run through you like the wind.