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How To Choose Between Two Women? (When You’re MegaDating)

By Emyli LovzOctober 21, 2019Strategy
how to choose between two women

Wondering how to choose between two women?

Generally speaking, men usually aren’t lucky enough to be faced with the conundrum of choosing one woman over another. Yet such a delicate situation isn’t reserved for only the Don Juan’s of the world. You too can find yourself staying up late at night creating a pros and cons list of your romantic interests’ best and worst features. The key to such a creating such dilemma is through MegaDating. 

Before you seek more moral counseling, MegaDating isn’t some shallow PUA tactic. Invented by yours truly, (an independent, women empowering female) MegaDating is the process of simultaneously dating multiple people so as to sharpen your dating skills and truncate the time needed to find and create a meaningful long term relationship. Before you start fantasizing about your misadventures as a newfound libertine, let me clarify. MegaDating isn’t about conquering the world with your penis. MegaDating is for those tired of waiting to find someone they genuinely give a damn about. 


Want to snap your fingers and make the woman of your dreams appear? 

That’s not possible (unless you live in Japan). The next best thing to hiring a genie is MegaDating. 

Now that you’re completely sold on the idea and have signed up for five dating apps, have been set up by your friends, attended speed dating events, met lovely ladies with shared interests on Meetup.com, you’re now probably dating various women at the same time. 

Those already acquainted with the romantic quagmires of MegaDating have no doubt already run into this issue. How to choose between two women isn’t an exercise for the easily clingy. Let’s think through the situation by taking into account the following aspects of your dating life. 

How to Choose Between Two Women: Set a # Of Dates Goal

There is no magic number here. The purpose of setting a number is to commit to creating a defined period of time in which you build a relationship before stamping a romantic dynamic with a label. During this trial of sorts, you won’t be asking her to be your girlfriend. Designating this time to learn more about each other safeguards against darting into a relationship you aren’t ready for. 

Settling is easy. Settling guarantees that you’ll have someone to cuddle up with on a consistent basis, but it could backfire. MegaDating and refusing to jump into a relationship will protect you from signing up for a relationship that’s mediocre. 

Personally, I’d set that magic number at 25 dates before making any type of commitment.

Sure it sounds kind of drawn-out, but would you rather that number be set too low or too high? Exactly. Going on one too many dates won’t backfire. Going on one too few means becoming exclusive with someone that you’re still unsure about. 


How To Tell If She’s ‘The One’: Focus On Your Feelings

Let that internal romance compass steer your heart towards making the right decision. Assuming you’ve given yourself enough time to get to know this person (cough cough 25 dates) there are certain signs you should be noticing. Search inward for that cliche Disney feeling that princesses get when they see their prince charming. If you don’t find that exact feeling it only goes to show that you haven’t been utterly brainwashed by Disney -congrats. That being said, those feelings of affection should be fairly obvious. 

If it takes too long to find those feelings -don’t fret- they might just not be there. And as much as you want them to, be careful not to synthesize feelings of affection. There’s no need to convince yourself that she’s your girl next door. When you’re MegaDating, you’ll realize that there are more girls next door than you ever thought imaginable. 

You might try to tell if she’s the one by uncorking your trusty magic marker and checking off some boxes. I’d advise against this. It’s the feelings that matter, not whether she’s into Bollywood movies or not. Love isn’t exactly logical. Trust the visceral emotions instead of trying to cram her into some boxes. 

If she doesn’t check off all your boxes despite the good vibes, it might be because you two have more in common than your superficial checklist suggests. It took my boyfriend and me years before we realized all the similarities we share that stem back to our childhoods. It’s weird but even after years we’re still finding even more ways in which we’re compatible. Had I ran my boyfriend through my checklist we might not have lasted. Time is the great sifter. Combing through the sand, always searching for a new way in which you and your lady are compatible. Don’t get too analytical. The feeling is either there or it’s not. 

How It Feels With ‘The Right One’

Do you ever think of her while you’re with this ‘other woman’? If so, run to her. C’mon man, if you’re thinking about kissing her as you’re off on some other date, then it’s time to ditch this ‘other woman’. 

Would you use any of the following adjectives to describe your time with her: free, easy, effortless, heaven? If so, she might just be the one. You shouldn’t have to search for these feelings. Instead, they should be bubbling at the surface. Identifying these feelings and letting them guide your decisions will save you from going on meaningless dates with women that aren’t ‘the right one.’ 

Being With The Wrong Woman Will Feel Like…

Sure there are the cliche signs that she’s not the one. If you say someone else’s name while having sex with her, then you’re probably in the wrong bed. Yet not every sign need be a faux pas such as voicing Stacey’s name whilst inside Rachel. 

Does your time with her feel forced? Forced in the sense that conversation is strained and that you feel as though you’re pressuring yourself to spend time with her? Instead of stealing glances at the cute blonde by the window are you making eyes at the clock and counting down the minutes until you can make your escape? 

Constant fighting and arguing are also telltale signs that she’s the wrong woman for you. This should also be glaringly clear when you juxtapose how you feel with her versus when you’re with your other romantic interest. 


Identifying who the wrong woman is should be easy when you’ve got something fresh and tangible to compare her to. Choosing between two women is easier when you have the ability to go on dates with different women in quick succession. 

Take A Trip Together With Each Of Them

campingThe aforementioned signs of distress are all dead giveaways that the relationship isn’t working out. But what do you do if both women seem awesome? You can’t keep dating both of them… right

Up until this point, it’s likely that you’ve only spent a few hours at a time with each of your lovely ladies. How will that dynamic change as the time you spend together increases? Long stretches of time together is what all long-term relationships demand. Answer this question by taking both of your ladies on vacation. 

Camping for a weekend or hitting up the vineyards and getting a hotel are fun and revealing ways to learn about the women you’re dating. Spending more than 24 straight hours together will test your ability to enjoy her company for such a period of time. It’ll also place you two in novel situations. How do you react when the car breaks down, when she gets hit on by another dude, or when your hotel reservation gets mixed up? 3-4 hour dates are safe. They don’t offer a rich host of situations where various aspects of her personality are tested. 

While sweeping your ladies off their feet, keep in mind that you’ll be paying. You haven’t reached the boyfriend-girlfriend phase so if you’re to propose a mini-vacation the funds must originate from your pocket, not hers. 

How to Choose Between Two Women: Definitely Meet Their Friends

how to choose between two womenIt’s not all about how you interact with her. Her friends may just be accessories to you but to her they’re integral members of her life, more so than even you might be. They’re permanent fixtures, you’re that dude from Tinder. If you want to have a starring role in her life you’d better get to know her supporting cast. These are the people you’ll be going on trips with, hanging with on lazy Sundays, and will be inviting over your place for game nights. 

If both women you’re dating are equally awesome, yet only one can be yours, why not let their friends be the deciding factor? 

When meeting friends for the first time remember to smile, remember their names and what they say, and ask thoughtful questions. I’ve also found that before meeting new people it’s a good idea to read up on the news. It’s likely that time-sensitive news will be broached. You don’t want to be left with a dumb stare on your face when everyone starts talking about an event you’re ignorant of. Hey, and if you don’t have cable, just download the Google Search app and customize your discover feature. 


Also come equipped with an interesting anecdote or news blurb/fact that you’ve heard recently. Your goal here is to attempt to bond with her friends. Some friends may look for the romantic interest of their friend to prove themselves. Reading up on current events and having a weird anecdote in your back pocket will make you appear intelligent and interesting. 

The Same Deciding Factor Can be Left Up to the Parents

Perhaps friends can be lost, exchanged, or ignored. Families however are much more ever-present monoliths than her buddies from college. The same rules that apply to meeting the friends also apply to meeting the folks. The main difference being that you’ll really want to be on your game when you sit down to meet the family. 

After meeting both sets of friends and family it’s time to decide which one you’d enjoy spending time with more. The winner decides who you’ll continue to date and who you’ll be dumping. 

See What Happens During A Conflict

Conflicts are inevitable. What should determine who you continue to court shouldn’t necessarily be the person who you clash with less, but rather the one who knows how to deal with conflict the best.

Which one constantly avoids arguments and opts to bottle her anger instead? Does one woman go from 0 to 100 in a matter of seconds? Which one has the better conflict management style? How someone deals with tense situations reveals quite a bit about his or her attachment style.  

What Happens When One Of You Gets Sick?

sick manYou’ve got a fever, strep throat, chickenpox, whatever the ailment might be you’re not getting out of bed. Is she coming over, watching a movie with you and cooking something for you or is she off gallivanting around with girlfriends?

You tell me which woman would you prefer to date. The one that’s at your crib filling your home with fragrant notes of cumin and turmeric from that Indian dish she’s cooking up in the kitchen or the one that’s, well, not there? 

Get Friends And Family’s Opinions On Each Woman

We don’t always want Ma and Pa’s advice. Quite often it’s unsolicited, dated, and just odd. But when it comes to who they think we’d be better with, our folks know a thing or two. They’re the ones that have been analyzing us throughout the entirety of our lives. 

If your folks haven’t spent much time around your ladies, ask your friends. Soliciting external advice from someone that knows you well can provide you with a unique perspective on the situation. Tap those close to you for their wisdom. You might just be repaid in a happy lifelong relationship. 


Talk Out Your Options With A Coach

If you’re still wondering how to choose between two women, a dating and relationship expert such as myself is seasoned in the practice of making difficult romantic decisions. Together we’ll weigh the pros and cons, examine the dynamic, and ultimately choose which woman is best for you. To learn how to choose between two women book a 1-on-1 Skype session. We’ll also determine if my 3 month coaching program could be the ultimate solution for you getting into that long term commitment you’re just might be seeking.