Medellin. The good, bad, and the ugly
First off the good. Someone said there isn't enough reviews of Medellin. It is an amazing place and most of the advice you will find is spot on. Here are some things I'm going to add I don't see a lot mentioned but likely go along with the same general theme. These are all just my opinions and I could be completely 100% wrong. But probably not 100%.
Spanish. I can't say enough how much better your experience will be if you are comfortable with basic conversational Spanish. If you don't know Spanish very well, wait 6 months to come and spend an hour or two each day working up your Spanish skills. Do a lot of listening because despite me having some Spanish skills, it is hard to understand when people speak it and you must be able to understand them to respond. Learn enough so you can be expecting what questions they may have when you purchase something. There is almost nothing you can ask for to purchase that there is not a follow up question. A simple one you will get a lot is they will ask you if you want a bag. They charge for plastic bags here. And there seems to be an infinite number of ways they can ask you if you want a bag. The last thing they will do is point to the bag or hold it up.
Most people are pretty polite when you can't speak well ordering food or trying to get into your accommodations. But even the nice people become clearly frustrated and it makes their jobs more stressful. The ones that want to please will keep trying to ask questions in spanish about every little thing. Then a few will outright show their displeasure, roll their eyes or their fellow workers will be laughing at their friend trying to accommodate the 'idiot' gringo who came to Colombia knowing no Spanish. It's just bad for our future as gringos showing up here with no knowledge of their language. You can get by. Don't get me wrong. You will still have a good time. But you are leaving so much more up to chance.
Now specifically with street women and freelance bar girls and Spanish. The ones that know English enough where you can actually communicate to them in english are the worst performers and worst value for your money. They speak half broken terrible english because they want more money from you. They use your lack of Spanish to re-arrange the table anytime they choose and prey on your ignorance of their language to shake more money out of you. It tells them in 3 seconds you don't know what you are really doing. They will charge you more than the colombian men for less services. Not all women of course. But on the street especially the one yelling out to you in english and trying to call and chase you down are the ones to ignore. The ones that are aggressive. Just ignore them. They will always be less value in my opinion and will try to charge extra for everything.
In fact I had already had several experiences with women coaxing me and targeting me and then trying to have a fun time with them. In all of the instances it wasn't 'terrible'. But they were all at the bottom of the list. Then after I already knew better and SWORE I would not go with a woman targeting me. Along came one who had the perfect ass, perfect tits, amazing face. That ass just took away my judgement. 50 k she said. Fair enough. This 'hot woman' was easily the worst of my mongering exploits. The combination of not being able to speak Spanish well and her being a straight up hoe bag made it just not so good. The sex actually wasn't that bad and she gave great eye contact giving head. But Every little thing. She wanted to charge me to not use the condom. Then when I told her to use it, she wanted money for the condom. The root of the problem is most easily cured by leveling up Spanish skills so you lead everything and are in control. You can't be in control if you don't know the language.
Aggressiveness goes into a general rule I now have. Ignore the aggressive ones. Many of the women are shy and reserved. Those are the ones you want. Because they are shy they will do what you want without asking for more money, asking for a tip, and endless stupid little things that for me was not about even the money. It just annoys the F out of me. It isn't always about paying more money. It's about not having to deal with the inscent begging and nagging for a dollar here and a dollar there. And trust me if you gave them $100 US dollars the women that chase you down and are aggressive on the streets will not let you go until they ask you if they can get another $10. Paying more or extra up front. The worst idea ever.
My advice is look for eye contact and a smile. If they don't come to you and can let you walk past a few times without losing their mind and trying to drag you into the building they would be a good one to approach.
Cleanliness. Get your teeth whitened. Get your nails manicured. Trim or shave you underarm hair. This applies mostly to women that are not street prostitutes. But even in those instances, since I have gotten my teeth whitened (they were pretty bad) it has made an absolute difference with every woman I've met here. I've avoided the women that just would not care I expect.
On paying more vs less and all that. I've got strong opinions as I've had many stripper girlfriends and lived with women that have pay to play dates. Even though women are charging money does not change the fact they have lust, fall in love, and have a lot of sex where they don't charge anybody anything. Most of the strippers and prostitutes I've dated, I would take them to swingers clubs and they would have sex for free with dozens of couples. That let me have sex with their hot wives and girlfriends. No money exchange at all. How do these strippers and prostitutes I know and lived with treat guys that pay them? Well it never would have anything to do with the amount the guy was paying and any guy paying was always at a huge disadvantage to having the best times with them.
Because when they are fucking for money it is a job. It completely changes their enthusiasm and more money I believe quickly moves them ALL into thinking "how much money can I get out of this guy? Every stripper and prostitute I've been friends with and lived with and had lots of sex with I never got them because of money. I was the guy that was cool with them doing their thing and judging them. There were with me because I was more fun, more interesting, and more exciting. All women want to be with the fun exciting guy when it comes to great sex. The guy that gives them money is a paycheck.
I pay to play in Medellin but very little. Most women I meet now are off of Colombian Cupid and then sometimes seeking. I've got women here buying me dinner, letting me stay with them, and several are literally in love with me and would have me move in. Not because I'm great looking or have money at all. They just want sincere attention. They have all been extremely sexual. More down with oral for extended periods than the street prostitutes. And super easy to talk to. Because they are not on the clock and actually like you they also are for more tolerant of your Spanish skills and will help you learn. I still monger for the variety but I know I'm not going to get the best of them by paying anything. Certainly not by paying more or extra.
Finally I would make sure to get a few dozen phrases down that tell people to leave you alone that are trying to beg or sell you stuff. Particularly in Pablado I've had a few physical encounters over overzealous street men (all have been men that get aggressive) trying to get me to buy weed, cocaine, or some stupid candy of some kind. Saying "No gracias" the first time is fine. But there are small minority that literally get their money from gringos through harassment. So saying no just once isn't enough. Their game is to keep hounding you until you give them money or get agitated enough to scream at them.
So I'll say along with this incident that knowing basic self defence and grappling is not a bad thing in an environment like what you will most come across in Medellin from my experience. Most of the problems are with single individual men that are poor and and rather desperate. They are more annoying than anything but they will put their hands on you sometimes and for me that crosses a line. Now I would be first to say always de-escalate and you need to judge the situation. I've had over 20 years of marital arts training so I don't scare easy particularly in a rather crowded area. In one incident I had a rather smallish street guy about 25 had asked me to buy weed or cocaine. I said 'no gracias' and kept walking. He then came up behind me and grabbed my arm and tried to stop me from walking forward. With that I grabbed the top of his hand and quickly just flipped it over and put him on his knees with a wrist lock. Very simple. I leaned down and yelled "tu comprendo No Gracias. I don't want your fucking cocaine" or something like that. Not my best moment. But when I have someone actually physically grab me in the street after they have already been told to leave me alone I typically am not going to let that go.
There were police not even 20 yards away that looked over as I still had him in the wrist lock and he was on his knees. I let him up and he apologised and went on his way. Cops didn't even move. But my next move was to leave the area. I think anytime you get into even a verbal confrontation with a local despite how it resolves best to not hang around and wait for them to get courage or find friends. I've actually not been back to El Pabaldo since that night. Not because I'm afraid it is just that you are constantly harassed for buying things or giving people money to the point I just don't enjoy being there anymore. Again knowing Spanish and not just saying "no gracias", but having something more meaningful to say to him in Spanish would have avoided the situation entirely. I would not handle it the same way again and should have stayed with a non-physical reaction to him putting his hands on me. But I think having some basic self defence skills in a place like Medellin goes a long way as it is very expensive to get quality training in martial arts in Colombia. I've read you can't carry a knife in Colombia as it is designated as a lethal weapon. Plus knives you have to pull out anyway. I'm sure there are better ideas, but I personally buy a bottle of coke in a glass bottle. Typically costs less than a US $1. I can drink the coke and I have that glass bottle which in a pinch would certainly make for a rather shocking melee weapon should the need arise.
That brings me to my final point. There are many fair skinned Colombians. One of the women I'm dating her son is as light skinned as I am. Many colombians are. So we get targeted as gringos mostly by how we act, how we dress, how we speak and where we are at. If you can speak Spanish well then with one sentence you will quickly be seen as someone to be respected and that has been in Medellin a while vs a gringo that just took the uber from the airport.
With all that said, you will have a great time in Medellin even if you just know Hola, con gusto, and Cuanta questa? But if you are coming to Medellin I implore you for our reputations as fellow gringos to learn as much spanish as you can before you come.