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8 Rules for Dating More Than One Person at a Time

8 Rules for Dating More Than One Person at a Time

Dating more than one person at a time is immoral, nasty, and sleazy.

If you had asked any man or woman 20 years ago their thoughts on dating multiple people simultaneously and chances are they would have responded with the aforementioned line. But that was 20 years ago.

Match’s annual study on singles found that 40% of singles have at one point dated more than just one person. Both men and women do it, with more women than men having reported dating multiple people at the same time.



The act may seem sleazy, but with only 19% of singles surveyed that dated various people simultaneously said they did so in order to have sex with multiple people. The jury is in on the matter of dating more than one person. Americans vociferously say that it’s all kosher… unless you’re a dick about it.

In order to get the most out of MegaDating and avoid being a douchebag, we’ll layout 8 golden rules to guide you through these overwhelming romantic times.

Rules for Dating More Than One Person at a Time

Always Be Transparent

This question shouldn’t come up until you’ve gone on several dates with the woman that posed the question.

If you’re asked this on the first date, a little red flag should be raised. She could be asking the question so soon into this nascent relationship for two reasons. One is that she’s a clinger and is already making plans for the future before the first date has even ended. The second is that she’s been hurt in the past and wants nothing to do with “players.” Either way, she’s deserving of an answer, and you’re going to give her one.

There’s no need to skirt the question if you’ve got nothing to hide – and you don’t.

Should she ask, enlighten her as to your thinking.

Tell her that you’re tired of waiting around for love to happen. You’re not of the mind that love happens by chance. You’d rather make your own luck by dating more than one person. In this way, the time it takes to meet someone special is shorted. Dating around is merely a way to expedite the time it takes to find your girlfriend.

Be mindful of the reasons you date women simultaneously before the date starts. Have a truthful and persuasive answer to supply her with so you don’t wind up looking like a libido-driven Don Juan.

Don’t Over Promise

With so many women on your dating horizon, the type of relationship you want with a woman you’re dating can change rapidly.

At first, you probably thought that Stacy, the Nat Geo photographer you met on Bumble was girlfriend material. But after a few dates, you concluded that she moves around too much and you’re much more interested in having sex with her than a long-term relationship.



That’s cool, feelings change.

What isn’t cool is refusing to vocalize your newfound feelings. With every date that goes by where you don’t define your relationship, she’ll naturally think that you two are headed towards a monogamous long-term relationship.

The moment you’re certain you want nothing more than bone, let her know. Don’t lead her on or waste time with someone that will never fit into the relationship mold that you want them to. Don’t waste your time grooming someone to be your summer fling or late-night booty call. This just wastes both of your time. Once you know how you feel about her, voice your feelings, and see if she reciprocates. If she doesn’t cool, move on to the next one.

If you need some help broaching this potentially awkward conversation, say, “I’m having fun getting to know you and I would love to explore sex with you but I’m not looking for anything serious and want to make sure we’re on the same page before moving forward.”

The quicker you rip off the bandage the quicker you rip open the condom.

Setup Cheap But Epic Dates

According to LendingTree, the average American male spent $861 on dating in 2019. Not much right?

But here’s the thing, that same exact study found that Millenials spent an average of $83 on first dates. If you’re MegaDating by dating multiple women simultaneously, you’ll go on at least 4 first dates a month. That means spending around $332 a month and almost $4/k a year on first dates alone. That’s a ton of money when you consider that you probably won’t see many of these women ever again. Also, keep in mind that this is just what you’ll spend on first dates. The $332 a month doesn’t include the cost of second, third, or fourth dates.

Luckily, there’s a more pocket-friendly way to date prolifically.

Adhering to MegaDating rules means spending no more than $20 on a first date and nothing on a second.

Yup, you heard right.

Think about it. Why would you invest a copious amount of time and money on a stranger? Sure there could be romantic potential, but at emlovz we don’t advocate going broke and betting heavily on potential.

First dates are opportunities to dip your toes in the water, nothing more. That’s why first dates should last no more than an hour and are financially capped at $10. If you enjoy this person’s company, cool, invite them out on a second date.

Second dates should be free, outdoors, physical, and involve quite a bit of touching. Spending a limited amount on the first two dates ensures that you weed out gold diggers and that you’re not going broke while dating more than one person.



Making it to the third date should mean that you’re into her. So much so that there are no financial restrictions on this date, in fact I encourage you to splurge. The date should take place at night, have no financial or time limits, and take place close to your home.

Why close to your home you ask?

We’re all adults here.

There’s only so much drinking, chatting, and dancing two people that are romantically attracted to each other can do before having sex. By the third date, the sexual tension that’s been mounting should culminate in an amorous congress.

epic date

Keep Other People’s Emotions In Mind

The more often you go out with a woman, the more serious she’ll think the relationship to be.

Taking a woman out 7 or 8 times is a sign that you want more than a hookup/friendship. As soon as you feel her emotions change have a heart-to-heart with her about your relationship expectations. 

At some point, both parties will want to label what they’re doing. If you can sense that she wants to define the relationship, broach the subject so that both parties can spell our their feelings and expectations. Use the utmost amount of tact when discussing how you feel.

Stay Protected

Don’t be a dick, wear a condom.

When you’re sleeping with multiple partners you owe it to yourself and the women you’re dating to get regular STD checks and be sure to wear a condom.

You’ll be surprised by the many opportunities you’ll have for having sex when MegaDating. If you’re dating at least two women a week, chances are you’ll quickly form a connection with at least a woman or two a month. Inevitably these strong connections will culminate in sex.



Protect yourself and those you care about by wearing a condom and getting checked for STDs.

If you’re not into wearing a condom, let this little scenario convince you otherwise. If you were to contract an easily transmittable STI you’d be out for the count for at the very least a couple of weeks. In this time you won’t be having any sex.

Furthermore, the women you were having sex or were about will be disappointed and question why you aren’t inviting them over. Do you really want to explain that you’d like to have sex with them but can’t because you’re taking antibiotics for your syphilis?

safe sex while dating around

Realize When You’re In Too Deep

My boyfriend was once single in SF for 6 years.

He was deep into the singles scene.

He stayed out late at bars, spent tons of cash on strippers, dated multiple women for somewhat selfish reasons, drank an unhealthy amount of Redbull vodkas, and ghosted women, among other things.

Once he told me that his actions compounded one another and quickly lead to an unsustainable lifestyle.

First, it’s going out once a week, then it’s a couple of times a week, then it’s finishing off a night at a rave.

Notice when your morals and values change.

Date multiple people for the right reasons – to find yourself a suitable long-term partner. And if that’s not your reason, cool, but be real with the women you’re dating. Don’t try and drag them along if you’re not interested in a relationship.

Be real with them early on. Often you’ll find that women decide to be friends with benefits and won’t become clingers when you’re real with them and manage expectations early on.



Keep Your Goals in Mind

Why are you dating multiple people?

How long do you want to date multiple people? What type of person do you want to meet? Where might you find that person?

As you date more than one woman, check back on your goals to ensure you find what you’re looking for. Update those goals over time, as you learn what it is that you like/dislike about all these dating partners.

It’s easy to get caught up in the Don Juan lifestyle – just ask my boyfriend of a few years ago.

Stacking dates, meeting new people all the time, kissing a new woman every week, and thinking you’re falling in love with a host of new women every month is intoxicating.

But is that what you’re really after?

Constantly reassess your goals and make sure that you’re adhering to them.

If you don’t know what your goals are, I know someone that can help you.

marriage

Should You Tell Her You’re Dating Other People?

We have to circle back to this question.

Naturally, this question will arise or maybe you’ll feel a need to tell her, or it’ll just come out.

Let’s start by addressing what to do if she asks if you’re dating other people.

First off, tell her the truth.



Keep your explanation short and sweet and tell her the following…

I’ve gone on a few dates with other women, yes. My goal with dating more than one person at a time is to compare and contrast enough women in order to find the best match for me in order to have a happy and loving relationship. 

To be honest we haven’t seen much success when students lie about dating around.

So tell her the truth. You’re being proactive because you want to find a girlfriend. The best way to do that is to meet new people.

Now of course there’s no reason to expand and tell her you took Tanya to Denny’s last Friday at 8 pm. Furthermore, don’t tell her that Tanya ordered the chicken salad with mandarin slices and almond slivers and then proceeded to lick her fingers will making direct eye contact.

Give her the line we’ve supplied above and move on.

This date is about you and her not you and the other woman you’re dating.

And definitely do not get too deep into the specifics of your dates with other women. They don’t need to know, and they probably wouldn’t want to know if you told them. 

Female Curveball: She may ask you if you’re dating anyone else. She may even appear to want to know a lot about the other women you might be seeing. She may look like she doesn’t care that you’re dating many other people. She may even tell you that she is dating around herself. THIS IS A TEST, DO NOT TAKE THE BAIT.

If you get into hot water, use the old adage “a gentleman doesn’t kiss and tell.” 

Most women won’t ask you whether you’re seeing someone else until intimacy arises. You should not offer up this information unless it is specifically requested. 

And if it comes out organically that you’re dating around, that’s fine. You don’t need to hide that fact. Just be sure to tell her why you’re dating around. If she catches a glimpse of your cards, lay them out on the table.

Reach Out For Help

In an ideal world, we’d have a coach for every aspect of our lives.



We’d have a nutrition coach to help us eat better, a chef that teaches us how to cook, and a career coach that helps us climb that ladder and get that raise you know you deserve. Teaming up with professionals that know what the hell they’re doing without a doubt has its benefits. The question you need to ask is what area of your life do you want to improve right now?

If you’ve read thus far, it’s transparently obvious that you want a romantic reboot.

As your professional dating coach I can show you how to meet and woo your next girlfriend.

When you enroll in our program, Dating Decoded you’ll learn the skills you need to get your flirt on with anyone, anywhere.

Via our online curriculum, live dating sessions, online community, and mock dates we teach men everything they need to know about scoring a new girlfriend.

We touch on every aspect of dating but pay special attention to helping you dominate the online dating scene. Almost a majority of new relationships start online. If you’re not meeting women online you’re missing out on a grand opportunity to meet amazing women. Dating apps can make you feel as though the game is rigged, but we’ll teach you how to defy the odds when we help you build a profile and teach messaging strategy. 

Throughout the course of you’re journey you’ll be supported by men that know exactly what you’re going through. We only accept men in our program. As such we’ve created a support community full of men that understand each other’s journey. As we have students enrolled across the country not only do our students chat online but also IRL.

Our program is designed to help you go from no dates in years to scoring dozens of dates in just a few weeks.

If you don’t believe we can walk the walk, book a book a 1-on-1 new client Zoom session to begin your romantic makeover or just listen to how our students’ lives have changed as a result of enrolling in our program.

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