What To Look For In A Woman

Guys are surprisingly bad at knowing what we want.

"I call bullshit!"

“Nope, feeling pretty sure about this one.”

No, seriously. Ever been hanging out with a buddy who insists that every woman he’s ever dated is “a complete psycho bitch“? Or the friend who seems to attract constant drama llamas who are continually having some sort of crisis in their lives? How about the guys who keep getting dumped over and over again or the ones who fall in love at the drop of a hat with women who will only break their hearts?

Maybe you know (or are) a guy who’s sole criteria is that she has to be a “10” or that she’s got to represent some hard to get “type” that’s always been out of your reach  – the cheerleader who spurned you in high school, the hot party girl you never could get with, a big-name cosplayer with the awesome League of Legends costume at NYCC. Maybe she needs to be the Manic Pixie Dream Girl to bring excitement and adventure to your life.

There comes a point when you have to be willing to admit that the only common denominator in all of these failed relationships or attempts at relationships is, well, you. If you keep going after women you think you want but are fundamentally incompatible with, then you’re just begging for heartbreak.

All too often there’s a serious disconnect between what we think we want and the people we’re actually compatible with. Sure, it’s easy to say “yes, Scarlett Johannsen and I would be perfect for each other” when you’re looking at her on the cover of Esquire, but unless you’re already somehow in the industry, your lifestyle and values are going to be night-and-day different.

...whereas I KNOW Kat Dennings and I could make it work. If that stupid restraining order wasn't in the way, anyway.

…whereas I KNOW Kat Dennings and I could make it work. If that stupid restraining order wasn’t in the way, anyway.

When it comes to finding an awesome woman, you have to know what you should be looking for.

Is Her Lifestyle Compatible With Yours?

One of the first questions people ask when they go on a date with somebody is “what will my life be like if this person were my girlfriend/boyfriend?” Your lifestyle plays a key role in your dating life and if yours don’t sync up, then the odds of the two of you working out go down exponentially.

Let’s say that you work a standard 9 to 5 job; you know exactly how your weeks will go – you clock in, you put in your eight or nine hours, you clock out on Friday and are ready for the weekend to commence. You may be tired at the end of the day, but at least when you’re done with work, you are done. You don’t need to spend time answering emails or putting out metaphorical fires at 11 PM; your time off is your time off.

Meanwhile, you’ve got a crush on the hot bartender you’ve seen at Starbucks, and she’s into you too… but the two of you almost never manage to actually schedule a dateHer day doesn’t start until around the time you get off work and don’t end until 4 in the morning.While your weekends are your time off, they’re crunch-time for her, leaving her exhausted the next day. And that lawyer you’ve been flirting with at your friend’s party? She’s been working 60-80 hour weeks ever since her firm took on that big client; there are days when it seems like she only goes home to shower and change clothes if she’s lucky. It’s hard for her to make plans because her time is so rarely her own – there will be plenty of times when she needs to work late, when she’s going to have to go over files at home and cancel even long-established plans in the name of getting the job done.

"Well, so much for seeing The Book of Mormon this weekend..."

“Well, so much for seeing The Book of Mormon this weekend…”

This, incidentally, is why it’s often difficult for single parents to date; weekends are almost always taken, staying over is difficult and plans are regularly interrupted by child-related emergencies.

But compatible lifestyles are about more than just scheduling issues, it’s about what you do with your life in general. We date who we are, and if you’re trying to date someone who’s radically different from you, then you’re going to run into trouble and heartbreak very quickly. If you’re more of a homebody who likes to get together with a few close friends for some rounds of Carcassonne, you’re going to be very frustrated trying to date somebody who wants to go out clubbing and bar-hopping. If you’re the outdoorsy type who likes to go mountain biking and taking long hikes out in the woods, it’s going to be more difficult to make things work with a devoted city-mouse whose definition of “roughing it” consists of a hotel with slow wi-fi. This is one of the reasons why the cheerleaders tend to date the jocks instead of the nerds – they have more in common and share a more compatible lifestyle.

This isn’t to say that differing lifestyles can’t work – much like introverts and extroverts there will always be people who can find ways to accommodate their different needs without alienating or trying each other’s patience… but it’s going to be much harder.

And while we’re on the subject:

Do Her Values Align With Yours?

This is another area that’s tricky to navigate. It’s easy to find somebody who’s your perfect match except for one area… and that one area could be the thing that brings it all crashing to the ground. More often than not, this is a matter of values – what you believe in, what you hold sacred and what you believe to be important.

The ur-example is, of course, religion. Many people have a hard time reconciling how they feel about somebody with the fact that they come from a different religious faith, whether it’s Catholics dating Protestants, Christians dating atheists or Jews dating Muslims. In fact, many branches of the Abrahamic religions specifically ban dating outside of your faith. Even if the two of you are able to navigate your own personal feelings about religion, it could come up again if and when you have children – how will they be raised? Even if you plan to give them the choice, it can become a contentious issue, when even the extended family gets involved.

But values go beyond your sense of morality or belief (or lack thereof) in God – it also includes what you prioritize in your life. Are you highly ambitious, chasing after a specific goal at work, or is your personal time more important? Do you believe more in the individual or in the community? Do you prefer to have structure and order in your life? Then the last thing you’re going to want to do is date a self-described “free spirit”. Are you the sort of person who treats his body like a temple? Then you’re going to have a hard time relating – or even tolerating – somebody who tends to treat theirs like an amusement park.

So, crammed full of dubious chemicals, covered in puke and graffiti and operated by carnies?

So, crammed full of dubious chemicals, covered in puke and graffiti and operated by carnies?


The thing to keep in mind is that you may think you want someone whose values are different than yours – someone whom you think counterbalances your own inhibitions or a lack in your life. The problem with this, though, is that you’re hoping for somebody else to make you a better – or more complete – person and those sorts of relationships only exist in the movies. Not only is it unfair to put the responsibility of “fixing you” on the shoulders of somebody else, but it tells other people that you’re simply not willing to put in the work on your own life. People are looking for a partner, not a project, and the only people who look for somebody to save are the people you shouldn’t be dating in the first place.

How Does She Handle Conflict?

You’re going to fight. It’s an inevitability. It may not be a screaming match or a heated argument, but you and your future partner will come into conflict. How often and over what will vary and you will wonder if you’re fighting too much or over stupid things and what does this mean for your relationship. But that’s not the metric you want to judge things by.

What you want to know is: how does she fight? Is she the sort of person who just explodes at the drop of a hat, or is she able to process what’s important? When the two of you are butting heads, whether it’s over the household finances or just whether you’re watching Vampire Diaries or Sons of Anarchy that night, are you able to actually have a discussion, or is it going to turn into a mutual snipe-fest as you aim to score points off of each other instead of resolving the matter at hand? Does she store old grievances like a passive-aggressive squirrel hoarding nuts for the winter or does she let go of the matter when it’s been resolved?

"...and this one is for when he forgot my birthday. And this one is when I caught him checking out my sister's boobs..."

“This one is for when he forgot my birthday. And this one is when I caught him checking out my sister’s boobs…”

You want somebody whose approach to conflict is to be sensible. You can’t expect Vulcan-like clarity or logic from anyone in the heat of an argument, but you want somebody who’s willing to hear you out, who’s willing to consider that she might be wrong and doesn’t immediately deflect or dismiss any legitimate grievance instead of throwing a huge fit, blaming you or trying to make everything your fault. Even if there’s an emotional burst at the beginning, if she’s willing to calm down and discuss things rationally, then everything has a much better chance of working out. A person who is willing to work with you instead of just pitching a fit is someone who’s looking to be a partner in a relationship instead of a superior.

Oh, and don’t think that this gets you off the hook; you have to be just as willing to calm down, listen to her side and be willing to accept responsibility and admit your own fault. It takes two to tango, and demanding only one person make concessions isn’t a relationship.

Fighting isn’t necessarily a bad thing – people can have disagreements, even passionate ones, over just about anything as long as there’s an underlying level of respect at the core of the relationship. But if she’s the sort of person who treats a fight as an opportunity to remind you of all of your short-comings, who can’t admit to her own faults or take responsibility for her own actions… well, then you want to find somebody else.


Is She Addicted To Drama?

There are some people who seem to always be in the middle of a crisis of epic proportions. Things are always going wrong for them. Friends betray them, bosses insult and belittle them, the universe has it out for them personally. Somehow things just always seem to explode around them and it’s never their own fault. Ever.

And they wouldn’t have it any other way. They’ll be the first to tell you “Oh, I’m a drama-free zone. I can’t stand drama,” and yet they’re always standing at ground-zero for the latest explosion or tantrum because it makes them feel important. It feeds into their need to be the center of attention without actually having to accept responsibility for their actions. When you’re in a perpetual state of crisis, then you’re the central figure of everybody’s lives.

Somehow the cause of more explosions than a chain-smoker in a fireworks factory...

Somehow the cause of more explosions than a chain-smoker in a fireworks factory…

As annoying as the drama queen might be, she presents a unique temptation to many men because she’s somebody to rescue. When you have low self-esteem, being able to ride in like the hero to calm the storm and save the day is incredibly appealing. It makes you feel needed. It makes you feel important. And when you feel as though you’re insignificant and worthless, this can be an intoxicating sensation. But there is literally no end to the crisises she will need you to intervene in because she will always go out of her way to make things worse… after all, she gets off on the drama and attention just as much as you get off on feeling like the savior.

Drama magnets are prime breeding ground for toxic relationships. They’ll undermine everything you’ve built  up in order to fuel another dilemma. They’ll continually drag you into their problems because they need an audience. And when you’ve become pliant to her whims and her games then she’ll leave you, because the ultimate drama fuel is to throw another man into the mix.

How Does She Make You Feel?

The most important question though, is simply, “how does she make you feel?”

"Well gee, how do you think, Doc?"

“Well gee, how do you think, Doc?”

It’s easy to get caught up in her looks – the thrill of a beautiful woman being into you is amazing, but those feelings tend to be deceiving. That initial rush of attraction goes away faster than you’d expect and then you’re left dealing with the real person, not just the collection of appealing features. I’ve dated literal models where I  realized that once you get past the looks… there’s really nothing else there. Sure, it’s nice going out with somebody who makes people stop and stare and wonder where to find the crossroads where you made your deal with Satan, but when she leaves you feeling cold or – worse – frustrated and bored, then you’re going to be miserable.

And how you feel when you’re with her is ultimately going to mean far more than what’s on the surface. A 101 who makes you miserable is ultimately less desirable than a  7 who makes you feel like the world is an amazing place and you can’t wait to see her again because she makes you laugh and you always have an incredible time with her.

So you want to ask yourself: Does she make you happy? Not in the sense of accomplishment – “look what I managed to land” – or in terms of external validation – “I’m nailing a hot chick, aren’t I awesome?” but in the sense of “I enjoy my life more when she’s around”. Does she make you feel like you can conquer the world? Does she make you feel like you could achieve your dreams? Does she make you feel at ease and content?

If she does, then congratulations: you’ve found somebody incredible.

It Takes Time

The thing to keep in mind is that you’re not going to know all of this right off the bat. It takes time to get to know a person – and that’s part of the fun. But as you’re looking for a future partner, keep these standards in mind. The more you’re aware of what you should be looking for in a woman, the more likely you are to find the relationship of your dreams. Because these are the traits of an amazing woman, and help lead to long-term dating success.


  1. Disclaimer: I really hate rating women, but it’s a useful shorthand with which to make my point []