Craigslist Chicago Personals: Tips for Hooking Up

Few websites have made it into general lingo like Craigslist has and the phrase has become synonymous with hooking up, one night stands and casual encounters.

But for all the hype, how easy is it to actually hook up in Chicago using the Craigslist personals section?

If you follow the advice we’re going to give you in our guide to making the most of Craigslist Chicago then you will find casual encounters an easier option when it comes to getting that perfect hook up.

Casual encounters for the uninitiated: How to use Craigslist like a pro

From its original heyday of being the ultimate place to meet people for anonymous and casual sex, Craigslist has had to weather a lot of controversy over the last decade. Where several years ago, getting a hook up on Craigslist was as easy as selecting from a list of possible candidates, the site has now evolved into more of a minefield.

A free classified personal directory, Craigslist made it possible for consenting adults to get in touch for whatever floated their boat; however, the site was quickly popular with paid services like escorts and adult massage which of course attracted the attention of the various prostitution laws that exist. The result? A big clampdown on these kind of advertising making it harder for Joe Public to sort the real deal from those services that are going to cost big bucks.

The truth is that Craigslist is populated with adverts from genuine advertisers looking for a no strings attached encounter as well as professional sex workers plying their trade. Whilst there is always a time and a place for escorts and women who want you to pay to watch them on live sex cams, if you are simply after a straight hook up then you need to be on you’re A-game when using Craigslist.

The trick is sorting out the difference and learning the best way to maximise your chance of success when it comes to getting a casual encounter in Chicago using Craigslist.

1)      Learn the lingo

As with any classified personals the site uses a lot of abbreviations for speed of use. However, not all of us are down with the patter so you need to know your BBW from your BBC.

You can use the site to browse by sections such as Women seeking Men(W4M), M4W Men seeking Women(M4W), Tranny seeing Men (T4M) and Men seeking Men (M4M)) or you can use these abbreviations in a general search of the personals. Casual encounters are generally shortened to CAS or you could use NSA for ‘No Strings Attached’.

Using the right search terms can help sort out those ads that just don’t apply to you but the general rule is, if there is an acronym or abbreviation then look it up; you don’t want any surprises.

craigslist for hooking up

Learn the lingo to avoid any nasty surprises. Image via

ISO means ‘In search of’ whilst HWP stands for ‘Height/Weight Proportionate’ and usually means someone is on the larger side of average and not that tall.

PNP is another abbreviation used on Craigslist. Meaning ‘Party n Play’ which could sound like fun to the curious but, be warned, this generally refers to sex on drugs. The drug in question is usually crystal meth; also referred to as ‘Tina’ or just by the capital letter, ‘T’. Even ads that use capital T’s in place of standard text could also be referring to the drug. Something along the lines of ‘wanT some fun TonighT?’ is a dead giveaway.

2)      Read between the lines

Many adverts are explicit about the nature of their services so escorts are easy to spot but with the new rules cracking down on such ads, many women are using more covert language to hide the nature of their activities.

As a rule, women looking for a ‘generous man’ or ‘gen’ will be looking for payment. Similarly, using the $ symbol as a substitute for the letter S can also be a code for a prostitute. Something like ‘Guy$ wanted for night$ out’.

Roses is also another word for dollars on Craigslist so if someone asks for fifty roses, they aren’t being romantic.

3)      Be realistic

Photos of women who look like they’ve just stepped out of a porn film complete with airbrushing and flawless lighting are a) very unlikely to be genuine or b) unlikely to be a free hook up. The consequences of answering ads like this are either going to be a bait and switch or end up costing you a lot of money.

4)      Develop skin like a rhino

Women looking for casual sex aren’t as common as men who respond to such ads so the numbers aren’t in our favour. If there is a post under CAS by a genuine lady looking for a hook up then she has all the power. It is likely that she will be inundated with messages so your chances of rejection are high. Don’t fret about it. Remember it’s not personal but this is a numbers game so you’ve got to keep trying.

5)      Respond well

Having said that rejection is high, the chances of success are greatly improved if you know how to respond well.

Remember, you are likely to be in direct and fierce competition with plenty of other guys so your first response to any nibble on Craigslist is important.

She may want casual sex but, as a woman, they will also want security that they aren’t meeting an axe murderer so be prepared to do some courtship to prove you aren’t an animal.

6)      Have pictures ready

Whilst most personals on Craigslist are wholly anonymous and do not include pictures, once you’ve made contact with someone they will want photos.

It’s simple, no photo, no sale. Have some ready prepared that show your ‘good side’ yet remain anonymous. You don’t want to have compromising shots circulating the internet.

7)      Lower your expectations

Just as you will probably over exaggerate your height or manhood the person you meet has also probably stretched the truth as well. That picture she sent you was probably taken several years ago and maybe she’s gained a few pounds since then. Just remember this and you won’t be disappointed.

8)      Go with your gut

Nobody who uses Craigslist for the first time doesn’t do so with a certain air of trepidation. There are plenty of urban horror stories of people meeting someone they hooked up with on the internet which turned out to be a scam or, worse, a dangerous encounter.

If your spidey senses start tingling then blow it off, some things are just too good to be true.

9)      Stick with the program

Lastly, just like you might do on occasion, some people get cold feet when it comes to the actual hook up so be prepared for last minute changes of mind. This isn’t uncommon and says nothing about you but is usually just nerves.

Don’t be deterred and remember that playing on Craigslist is a numbers game.