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I will be going to TJ with a mexican friend of mine who has been to TJ several times. Will a gringo hanging out with my mexican buddy be safer than just 2 gringos together? Will prostitutes come up to us trying to make a dollar?
I'm sure I may be hassled a bit with buying goods there from vendors and such. But I just want to know what I should expect. You will be very safe together.
Don't get wild and crazy and you will be fine. Depending on the area you are in, people will come up and try to make a dollar. I just got back from a 3 day trip and was asked for money for food by 3 school girls, money to go to the hospital by one man, and by several others. In the Coahilla red light district , there are usually hundreds of ladies standing on the sidewalk. I didn't see any of them approach anyone, just lots of smiles. Also for every couple girls, there are a couple of cops, standing right there.
In the dance and gentleman's clubs, the women will approach you, so if you find that offensive, don't go. Beggar children, sent on duty by their mother waiting nearby, will plead for money. Shop-owners will invite you to buy stuff. Hawkers in front of strip bars will invite you to come in and have a seat and have a beer and So, just be prepared for stimuli, intensity, as the tourist drag in TJ is not exactly a place where one is going to have a gentle, easy, peaceful meander.
If you venture into the red zone, be careful. I think having your friend with you there could be beneficial in that a lone gringo can be a magnet for unwanted police attention. Be safe, have fun, don't jaywalk, don't spit on the street, don't drink more than one or two, don't drive if at all possible, don't be rude, don't stand out.