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The Craigslist Conqueror is here to help you land a date tonight

Seriously, do not scour Craigslist for some sexy time tonight without reading this first. 


Molly McHugh


Posted on Feb 14, 2014   Updated on May 31, 2021, 6:16 pm CDT

For most of us, not having plans for tonight means we’re resigned (delighted, maybe) to spending the most romantic day of the year with a heart-shaped pizza and House of Cards. For some of you, though, maybe the action is just beginning. Maybe you’re going to get yourself a date tonight—someway, somehow.

If that’s the case, then you need to meet the Craigslist Conqueror.

The Craigslist Conqueror, real name Aaron Smith, is just your average guy… if your average guy has completely mastered the art of the Craigslist hookup. The operation began when post-divorce and 10 years out of the dating scene, Smith gave dating sites a shot. He wasn’t impressed; he was wasting money and didn’t make many connections. 

It was then that he turned to Craigslist Casual Encounters, though he admits it’s not an easy avenue. “If I wasn’t a decent writer with the willingness to explore and experiment on a completely anonymous forum, I’d still be living a very sad, solitary life.”

According to his bio, in the first 18 months of his Craigslisting, Smith met 150 women… and slept with more 120 of them. He shares his advice and stories in his books and blog now to help others in the same position find whatever it is they’re looking for.

But in the spirit of Valentine’s Day, he was willing to give us a crash course. I asked the Craigslist Conqueror for some advice on how someone might navigate the Craigslist scene today in hopes of finding a date, an adult sleepover, or maybe even that fickle mistress herself: true love.

What should you be looking for? Are there any keywords to keep an eye out for?

This is an easy one. If you’re in Casual Encounters, almost everyone is there for “RIGHT NOW.” Men and women both. Some are looking to meet within the next hour, some are looking for later in the evening. But for both men and women, Casual Encounters is all about the impulse purchase. And there is a half-life for conversations that start in Casual Encounters. As a general guideline, once your conversation goes more than five hours, it’s unlikely you will meet. If you talk for one day without meeting, then try to pick up the conversation the next day, there is little chance of meeting. And if you go three days without meeting, the odds of ever meeting are infinitesimally small.

Things are a little different in Men Seeking Women and Women Seeking Men. It’s a little more like a traditional dating site there. And some of the women in there are actually looking for rather quick meetings; they’re just trying to avoid all the guys sending pictures of their junk. But if you’re really looking for a quick hookup, your main focus needs to be Casual Encounters.

What should you avoid?

There are three types of posts on Craigslist of women looking for men, [and they are either] spammers, hookers, or real women.

I have 20 rules to avoiding spam in the book. Chapter 13, I believe. It’s a MAJOR time waster and it has chased many, many people off of Craigslist, although Craigslist does work hard to limit the spammers.

[As for hookers] …there are a lot of women out there who are in desperate need of money, that is just a fact of life. I feel bad for them. But no man should ever pay a woman for sex, it’s just not right, and it’s not something any man ever has to do.

If you know how to avoid the first two types, you should be able to spend 95 percent of your time on CL talking to real women. Now, from this point forward, just like meeting woman at a party, you have to go with your gut to decide where you want to take things. We’ve all been in the situation where we’re at a bar or party meeting someone new, and after about 10 minutes it dawns on us, this person is certifiably crazy. The same thing can happen in any online forum. Just like when it happens face to face, the best strategy is to back away slowly, no sudden movements.

What if you’re the one writing a post? Any advice there?

Oh my God, do I have advice. I have two whole books of advice! But I can give you the overview in just two sentences:

If you’re a woman, think like a man when you write your post.

If you’re a man, think like a woman when you write your post.

Should it differ if you’re looking for just sex or for a date?

Writing a post follows the same guidelines whether you’re looking for a date or for a hookup. Of course, what you write changes depending on what you want. But this one truth always remains: write it from the reader’s perspective, not from yours.

That sounds like common sense, but go to Craigslist in your city right now, and you’ll find the majority of posts from men looking for women include pictures of their sexual organs and demands that they need sex because they’re horny.

If things get awkward… what do you do?

Yes, of course things can get awkward. It’s not a regular circumstance to be having sex with someone within five minutes of meeting them face-to-face for the first time. We’re hardwired to feel a little awkward in those situations. The question for both people feeling awkward is this: how badly do you want the fantasy? If you want it badly enough you’ll push through the fear and awkwardness. What you’ll discover once you push through those feelings is amazing. If you don’t want it badly enough you won’t.

I give everyone this advice: be intentional in your breathing and in your speech patterns. Breathe deeply, deeper than you feel you have to. Continue breathing deeply intentionally until you feel completely comfortable. And intentionally slow down your speech patterns. People who are nervous tend to speak quickly. And that makes other people in the room nervous, so they speed up their speech patterns. So now you have a never-ending loop of nervousness. If you slow your speech patterns, you will feel more relaxed and so will the person you’re meeting.

OK, obviously we have to ask about doing all of this safely.

Safety is always vital, whether you meet someone at a bar or a club or you meet them online. There is a ton to discuss here, but the most important things I can say are:

1. Always trust your gut. Everything may seem normal, but if that inner voice tells you something is wrong, walk away. Fast. And never look back.

2. Use social media and Google to find as much as you can on the person you’re about to meet. The beautiful thing about social media is that everyone leaves an online footprint.

3. Use all of the same safety strategies you would use if you met someone at a bar, club or party.

Can a one-night Craigslist encounter become the real deal?

Absolutely. MANY of the guys who have used my book have sent me notes telling me they found their long-term girlfriends that way, But I don’t even have to go that far for proof that a CL hookup can lead to a lot more. My girlfriend and I started with a CL hookup. I went to her place, and we’ve been inseparable ever since, for more than two years.

And of course, how do you feel about Valentine’s Day?

I feel like it’s a mixed bag. The only holidays I really love are the ones established to remember something important, or to offer a chance to reflect. You could say that Valentine’s Day is an opportunity to stop and really appreciate your partner in a relationship. So for that, I think it’s not a terrible idea, however… I do have BIG problems with a holiday that is exclusionary to people who don’t happen to be in a relationship. It’s like we’ve created one day where everyone who isn’t in a relationship becomes a second-class citizen. I think that is cruel and unfair.

And I’m not even going to get too deeply into the idea that a holiday has been created to benefit greeting card companies and flower shops. I love commerce, but I don’t love being forced into it because someone says it’s a holiday.

So like I said, mixed bag.

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*First Published: Feb 14, 2014, 2:11 pm CST