How To Date Toward A (Good) Relationship (If That’s What You Want) Unflinching advice about getting real with a woman

So you’ve been on a lot of dates, and you keep meeting girls. You might even kiss said girls, and possibly go on to having a relationship—despite the fact that you don’t really like the person. Girls do this, but guys seem to exist in some weird world where they will bumble into these situations even more frequently, dating girls that simply don’t fit them, let alone the ones that are actually bad to them. Then there’re the guys who constantly get that first or second date but don’t so much as smooch at the end of it, then get a great email or text saying “Well, I just don’t have those feelings for you.”

My last columns are clearly a hit, as proven by the guys saying that I’ve been castrated and I should be fired, and thus I believe I am uniquely equipped to help steer them. Here are my six rules of the road to getting into a dating scenario that will be worth sticking around for.

This is specifically focused on the world of dating before making something into a permanent relationship, but it can be applied later in the game as well.

1. Be Upfront With What You Want (And Be Prepared To Not Get It)
If you want a long-term relationship, be up front with that. Don’t say “I’m looking for my future wife,” as you either sound like a time-traveling bounty hunter or a serial killer. Don’t just blurt it out mid-sentence, but put it on your dating profile online or say it at some point if it makes sense.

If at any time she says she just got out of a relationship and isn’t looking for anything serious, just walk away. Or, if you really think you have a shot and you’re several dates in, bring it up and ask her if that’s really the case. Just be blunt.

Why are guys not blunt? Because reality can hurt. And generally bringing up annoying things like “hey, are we actually going to work out?” can lead to her saying “no” and then she stops doing sex on top of you, removing your sex-having privileges—potentially permanently!

Sadly, you have to.

The mode to go into dating with, if you want a long-term relationship with the right person, is to go into it looking to have a great night. This means you are potentially going to, if you’re smart about it (versus looking to waste hours of your life), end up having a lot of first dates and then saying “Well, that didn’t work.”

2. For The Shy Dudes Everywhere: Say It’s A Date
Not every guy reading this (but more than will admit it) is just plain shitty at getting a date. I’m not talking about online dating, I’m talking about that girl they really like and they ask out. The most common guy problem I see, by far, is that these nice, normal guys seem incapable of facing the fear of rejection, so they say “oh, uh, let’s get lunch.” While it’s trite to summon up a Ryan Reynolds quote, let alone one from a forgettable comedy Just Friends, I always respond with “like a day date?”

That’s because that’s not romantic. I get lunch with workmates. Make it a night thing. Ask the girl out for dinner or drinks, and say “it’s a date.”

It took me many years to absorb the directness of just establishing that, in fact, you want to go on a damn date. I’ve watched male friends spin their wheels for months with a girl who clearly has no interest. They won’t say the word “date” because in doing so they complete a dark ritual that dooms them to a potential “no.”

Just remember folks: The girl can agree to a romantic date and still not like you anyway!

Which leads to my next point.

3. Death Is Certain, And You Won’t Get Along With Most Girls
If you truly want a relationship, you must marry yourself to the Death Is Certain principle.

That’s the simple rule you should live your life by—found on

That’s the simple rule you should live your life by—found on a weird t-shirt I stumbled across online—that death is in fact certain. This doesn’t mean that you leave a trail of bodies on the way to the bar, but that you and your potential date are, in fact, equals. In fact you’re equal with everyone on some level—we’re all born and we’re all going to die. We’re humans.

So, beyond the morbid statement here, the point is you have to be able to go into a date both wanting a relationship but marrying yourself to the concept that it’s perfectly fine for you to not like her and her to not like you. It doesn’t necessarily make you either of you bad people. Yes, I’m sure you will run into girls that are just terrible—they quote Atlas Shrugged, they complain about every single thing in the meal, they walk outside and buy a vial of cocaine mid-date (this happened to me)—but hey, maybe someone out there in this big crazy world wants a bump and some Ayn Rand. She’s just not for you.

The problem many people, regardless of gender, run into is that they will simply say that they want a relationship, take the first one that comes along where the sex is good and the person is attractive and they’re not awful to talk to. They’ll push aside their gut instincts. This is bad.

4. Pushing Aside Your Gut Instincts Is Bad
One of the smartest pieces of dating advice I’ve ever given was to take a girl to one of your favorite bars or restaurants—somewhere you love to go (though not your regular watering hole, that is a special place for later). Why? Because if she turns out to be not for you, you’ve had a good meal or a good drink in a place you like. It doesn’t even have to be an expensive place. Just somewhere you like, that you feel comfortable in.

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When she arrives, have a date. Talk about things. Is the conversation flowing naturally? Is she laughing? Or does she seem kind of bored and none of your jokes are hitting home? Do you try and move closer and she moves away? These are probably bad signs. Generally, if you feel like it’s going badly, it probably is and you should probably not continue any further.

The problem is, a lot of the things you (and god, I) push aside in the gut feelings department are incompatibilities you’re sure you can just get past if you believe in yourself, or her, or something. For example, you’re dating a girl you’re super attracted to, but you’re doing most of the legwork. She’s hot and cold. She’s unresponsive, or you text way more than she does. You know why that’s happening? She’s just not that into you, like the book and movie of the same title. Once or twice it might be because she’s busy, but guess what? If she suddenly shifts from talkative to not talkative, she’s almost certainly not into you.

There’s also the reverse scenario—where you’re dating someone and they’re super into you, but you feel a weird sort of tugging at your soul whenever they text to hang out. But you go. You have sex. It’s… fine. You’re fine. They like you, you like them, you have sex, you do things together, you’re together… that’s what you’re meant to do, right?

Nah.

If you really want a relationship, which I assume means you want to meet that one special person, you have to be somewhat ruthless without being a jackass. It also means you have to be prepared to say, though not abruptly, when things aren’t working out. This can be on date one where you realize that you fundamentally see the world differently—religion, music, finances, and so on—or can just be the fact that you plain don’t fit. If your conversations are boring as shit to you, and you want a relationship, but gosh darnit she’s just so damn cute, why I oughta, you shouldn’t stick around. No, I get it, you want to have sex, and if she wants to have sex with you too then by all means do it, but don’t fake some approximation of relationship-ness to get it. If you do, you have to live with yourself, buddy.

Finally, that spark that people talk about isn’t that heart-thumping, “holy shit, I’m gonna have sex!” feeling, or the excitement you have when you’re together the first few months (which is even quite rare). It’s a few months in when you’re truly comfortable around her—and how she reacts to you when you’re not quite perfect. When you break down about something and she’s there, or she isn’t. She may not react the way you need, and it’s okay to make the decision to say “nah, this isn’t the person for me.”

5. Don’t Settle, But Also Get It When She Won’t
It’s actually very good advice to not settle based on your gut instincts. If you’re dating someone and you are truly comfortable with them, that’s a powerful feeling. It’s a warmth that you’ll feel. If you feel like you’re forcing yourselves to do activities to just keep that good feeling going of “We’re dating! It’s dating time!” then you are probably in a bad situation, one you should tap out of.

Guys and girls really love to just stick around, because it’s easier to sit with something kind of good than go out and look for something great. It’s got sex in it. She totally sleeps next to you and that’s a nice, warm feeling of being wanted. But it isn’t enough if you want a relationship that will be long-term, if not one of those permanent ones with a ring and stuff.

It’s also because leaving someone that you’re in a happy but not great dating scenario/relationship with is so difficult. Of course both of you want to stay together. It’s good. But it’s not the one.

Also, and sort of related, guys have a tendency to get mighty huffy when they get turned down by a girl. I’ve been there, man. You’re really into this girl, you think damn, she’s funny, she’s talkative, she’s chatty. Then whammy, she’s saying she doesn’t really think you’re for her. You get mad, you want to convince her to stick around.

If you have to convince someone to stay with you then you probably aren’t meant to be.

6. In Conclusion, Be Real With Yourself
To end up in a great long-term relationship, you’ve got to be prepared to walk away from shorter ones. If you find yourself only excited to see the person for the sex, that’s fun but also bad for long-term prospects, as however long you last in the sack has all this other time around it.

Also, and this isn’t sexist or mean to say, you may simply not be that attracted to them but really enjoy spending time with them. There’s a balance there—looks aren’t everything, and they do fade, but you need to match up on a sexual/physical level.

What sucks about all of this stuff is that sometimes, finding the right person is really, really hard. If you want to fall in love and all that good stuff, you’re going to go on shitty date after shitty date after shitty date. You can take breaks, but don’t make the mistake of sticking to someone because it’s been too long since you had a relationship. There’s no shame in insisting on finding someone right for you.