How to Date Multiple Women at Once

We’ve all thought about it. How wonderful it would be to date more than one woman at the same time. Unfortunately, most of you don’t have the stones to actually do it. We understand the moral hang-ups that go along with it, but sometimes commitment just isn’t something you want to deal with. If you play your cards right, you can date a handful of gorgeous hotties without even breaking a sweat–and if you do it properly, you can avoid hurting somebody’s feelings. So sit back, take notes and let us help you find the balls to keep it casual with multiple women at the same time.

Lock your phone

This might seem like an obvious piece of advice, but you’d be surprised just how many great men have been undone by the reading of a simple text message. Do your duty and set a lock on your phone if you plan on being involved with a number of different women at once. While it’s in their nature to be a bit nosy, let’s face it, who wouldn’t be a little bit curious if a text message came in while their significant other was out taking a shit? That’s right, absolutely fucking everybody. So do yourselves a favour boys and girls, set a password, and lock your fucking phones.

Segregation is key

This one is super important. The main staple of seeing multiple women is that you do not, under any circumstances, ever want them to meet. Or better yet, you don’t even want them to know that the other exists. This means a few things:

1. No friend overlap: this is important. Not only does this mean they can’t know each other directly, they can’t even have any friends in common. Friends talk, especially girlfriends, and if they even catch a whiff that you might be fucking around–or are just being a touch dishonest–they will bring your whole operation crumbling to the ground.

2. Divide and conquer: one of the keys to successfully keeping up your facade is to divide the city. Even if you live in a small town in butt-fuck nowhere, draw an imaginary line right down the fucking middle and make absolutely sure that you keep each lady in their respective zones. This can get really complicated once your roster reaches about three or four, so be careful before you bite off a bit more than you can chew.

3. Avoid introductions: not only is it important to make sure they don’t know each other, but if at all possible, make sure you never meet their friends (or let them meet yours). But why, o wise editors of The Chalkdown? Why can’t I meet her friends? Well, meeting her friends will give her the false impression that you actually want to be her boyfriend. The less she thinks you’re into her, the easier it will be to keep things casual. Besides, her friends will undoubtedly start snooping around your private life and bring you down faster than you can get your pants down for one last fuck in the nearest McDonald’s bathroom.

Never commit to anything, EVER

The key is to create the outward appearance that you haven’t actually committed yourself to any of these women. keep things loosely defined. It’s important that you treat every one of them nicely and with respect while still maintaining a stern front that you don’t want anything to do with them in a serious context. It’s a morally ambiguous line to walk, but technically, if you haven’t committed to a monogamous relationship, you aren’t really doing anything wrong. So when it inevitably comes time to have the dreaded talk, keep it loose and casual. There’s no shame in not wanting to have a serious relationship.

Write shit down

Going for the glory of a full roster means that you might have to compromise your moral code just a teeny little bit. And by teeny little bit, I mean that you might have to forget that you have one entirely. While you might not have actually committed to anyone, you sure as shit are still definitely gonna have to lie to them. There’s no way around it — if you’re going to go down this path, it’s going to get busy, and when things get busy, you’re going to have to lie. There are only so many days in a week, and when it comes down to it, sometimes you’re going to have to lie about where you’ve been, or more often, where you’re going to be. It’s for that very reason it becomes absolutely integral that you WRITE SHIT DOWN. The best way to go about it is to keep one notepad for every woman you’re seeing. On it, you can make up a grid of where you said you’ve been for any given day of the week. While technically you aren’t doing anything wrong, women do not like it when you date other women. So if you get caught in a lie, this magnificent house of card you’ve built will all come crashing down in a blaze of fire and former glory.

If you’ve got the balls, go after what you want. Follow these rules and significantly minimize the chance that one of your lovely dates will figure you out and toss their drink straight in your face. Or worse yet, break a bottle on the back of your fucking head. Get out there and have yourself a good damn time.


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