How To Date Multiple Women At The Same Time

by Adam Shadows
Kayla Snell

I rarely date three women at the same time. It stretches you thin, and after a while, you feel as if you've been swallowed up and spit out by the sea.

Dating three women at the same time is asking for trouble, like a squirrel spending too much time in the street. You could even do everything right and still find yourself all squished and shit.

So, I like to stick with two. Sometimes I'll push, but usually it's two. Two is a healthy number. It's easier to process things in twos, probably because that's the quantity so much of us comes in. Eyes. Ears. Arms. Balls.

Maybe dating two brings me some sort of whacked-out balance or something. I haven't dated just one girl at a time for over a year.

I don't know why I do these things. I just know that I do.

New York is a great place for this. It's a little more expensive than, say, Boise, Idaho, but there are way more places to hide. I don't know a thing about dating multiple women in Boise, Idaho or Birmingham or Phoenix or anywhere else. But if you want to do it in New York, I can offer some guidelines and pointers.

Let me clear some air before we continue with this, which is undoubtedly the douchiest post I've written yet.

One, I know this is the douchiest thing I've written yet, and it probably will be for some time. Two, I'm in no way saying you should date multiple women or should even want to. And three, by putting this in print, I'm not advocating in any way that I'm right or righteous in the least, nor am I trying to tell you this is what all the other guys are doing.

In truth, I've never met another guy like me in my life (for better or for worse).

That new guy you're talking to is probably looking for the same things you are. So, don't mistake this as something representative of what all males feel or want.

But, if you met a guy like this or want to be one on your own, or if you're bored or tired or in a rut, I sincerely suggest pushing your limits and seeing the world in twos. It may drive you wild. It may drive you insane. It may just work.

Life starts slowing down as you get older, and this is just how I like to keep it going fast. I can't really dance around the topic any longer. I date multiple women at the same time.

This is how I do it:

1. Choose your date wisely.

Lately, I've been trying to date only girls who are new to New York. This is a very large and specific group.

Girls who are brand new to New York have convinced themselves they are ready for adventure, for wonder, for whatever. They go see comedy shows in Times Square. They give homeless people their change. They won't eat the street food. They aren't New Yorkers yet, and many of them won't last long enough to ever be.

They've all seen too much "Sex and the City," and then they get here and spend every night binge-watching it because they don't know anyone and won't go out alone. They live in Gramercy for now, until they move to Alphabet City, then Bushwick, then BedSty. They can't believe the rent.

Since I always view dating as a short-term endeavor, I try to make my dating as symbiotic an experience as it can be. Girls who are new to New York are looking for friends.

I'm there to be a friend, a tour guide, a dash of the local to make them feel like they've arrived and already belong. I'm their first New York story because I'm the only one in this enormous city giving them the time of day.

Soon, I'll be their first New York screwup, and that's a milestone they'd secretly been hoping to hit as well. After a while, they start to make some real friends. They start to get acclimated. They start to find ways to fill the days. I can fade away.

Girls who are new to New York don't know what it's like dating in New York. They're spending so much time just trying to acclimate to the city, to the streets, to their new jobs and to all this newness hitting them like a bag of bricks in the face every second of the day that they won't make serious demands on your time. And it gives you time to meet others.

They also don't have those New York friends who already know you're a dick.

2. Completely disconnect yourself from the outside world.

This one is probably the most important. Get off Snapchat. Get off Instagram. Get off Twitter, for your own sanity if nothing else. You can keep your Facebook for posterity's sake.

Those other social networks will only get you in trouble if you're dating multiple women (especially Snapchat).

Think about it: Snapchat is basically a built-in security camera to your life that we prance around like a projector. No, it isn't good for everyone to know what you're doing at this exact moment in time. No, you do not want to showcase who you are with right now and what kind of poorly made cheesecake you're eating.

Only harm can come from Snapchat. It can only broadcast your own stupidity. It can only get you caught. Good God, it hurts just thinking about.

I invited some friends out for my birthday this year to a three-floor bar. I didn't invite either of the girls I was seeing. But one was there, just a floor below me, the entire night. She doesn't know I know this. But I know she thinks I went somewhere else because I told her so, and there isn't a stupid Snap story circling to prove me wrong.

Think about if every text you received warranted a 360-degree view of you and your surroundings as a response. That's Snapchat. You wouldn't be able to get away with a thing, even if you weren't doing anything wrong.

3. Take them to the same places.

This might seem counterproductive. Wouldn't bringing all your girls to the same places result in them running into each other? Not if you choose your spots carefully.

Take the new to the city girls to bars you know they'd never go back to without you. Take them to Tuesday night bars with Tuesday night crowds, so on Friday, they bring their gaggle of girlfriends to the high-end Meatpacking places instead.

Also, you'll have an intimate time with her at your bar because there will be no one else there, and if you're lucky, she may even deem it “your place” in her head and not go back without you.

4. Make sure it isn't your place, and then make sure you leave.

How many hordes of marriages have begun as one-night whatevers, turned into two-night affairs, turned to oh-shit-it's-Monday-morning-and-I-haven't-been-home-yet endeavors and snowballed on and on from there?

Make sure you are the one with the power to leave. Then, make sure you do. Don't risk falling into a love trap by spending too much time with one person.

Have a good night. Don't risk next week for a long weekend.

5. Write under a pen name.

That way, when they don't know where you live, they can't find out.