My "Five Rules", a Guide to Navigating Dating Waters

As a high school youth minister, I find myself working with kids in the throes of the turbulent dating scene.  A scene which I, thankfully, departed back in 2010.

The years spent navigating those waters are stressful.  And much of the stress comes from the inability to know the other's mind.  While it is impossible to know the intricacies of every situation, it is fair to say that patterns emerge.

So one of the talks I love to give are my "5 Rules for Dating" (and 1 suggestion).  These are the culmination of all the hard lessons I learned on the way to the altar.  They are clearly told from a guy's perspective, but both sexes have something to learn.  And I think knowing them can save a lot of heartache. 


Rule #1:  If the answer is not immediately yes, the answer is immediately no.

The first rule is perhaps the most important.  Exceptions to this rule exist, but the odds of being that exception are somewhere between winning the lottery and being struck by a golden meteorite.

Guys are typically tasked with working up the nerve to ask the girl on a date.  But an odd thing can happen when we do… the answer can come back as ambiguous.  Rather than a “yes” or “no”, the guy receives an answer like, “I’m busy that night” with no elaboration or proposed alternative.  The key question – (whether she wanted to go on a date) – went unanswered.

Why is that?

Let’s shift perspective.  From the girl’s point of view, a guy has sprung a choice on her.  She wants to say "no", but that would seem harsh and confrontational.  So instead she resolves to “let him down easy” by giving an impersonal reason why the answer cannot be “yes”.

As a result, the guy will walk away uncertain of where things stand.  And he will likely try again the following week... only to get another vague answer.  Eventually he figures out what’s really going on – a realization which is way more emotionally difficult than just receiving a straightforward “no” from the start.

Lesson for guys: All, non-yes answers should immediately be considered a “no”.  Period.

Lesson for gals:  Give unambiguous answers and make sure the guy walks away knowing where things stand. “Letting him down easy” is actually letting him down slowly and painfully.

Rule #2:  If she cheats for you, she cheats on you.
(Symmetrical rule)

I once knew a guy who thought he was awesome because he "stole" a girl who was dating another guy.  Then he was shocked when she turned around and left him for yet another guy.

Stealing the girl doesn't mean you're awesome.  It just means you're dating a girl who is willing to cheat as soon as the grass seems greener elsewhere.

Lesson for guys:  Don't pursue a girl who isn't single.

Lesson for gals:  Same deal.  Guys do this too.

Rule #3:  The relationship must be between equals.
(Symmetrical rule)

When pursuing a woman, a guy needs to ask himself:

 "Am I her equal?  Am I imagining her stooping down for me?" 

Or conversely:

 "Am I thinking I’m settling for less?  Do I think I'm doing her a favor by asking her out?"

In either case, the resulting relationship would be toxic.  A successful and happy relationship must be a partnership of mutual respect between two equals.  This doesn’t mean the two people need to have all the same strengths.  It means there can’t be an intrinsic sense of inferiority or superiority between them.

Lesson for guys:  If you don’t think you’re on equal footing with the girl you’re pursuing, stop and rethink.

Lesson for gals:  Same deal.

Rule #4:  Don’t try to be the perfect “nice guy”.  Become an interesting and impressive man.

When asked what kind of guy women are interested in, many women will say they are interested in “nice guys”.  That is to say, someone who is unconditionally friendly, polite, patient, kind, thoughtful, and empathetic. 

Taking that advice to heart, many guys will polish those virtues to a mirror shine.  Then, to their utter consternation, those same girls will go off and date total jerks.  What is going on?

The answer is that they don’t really want “nice guys”.  However, they don’t want jerks either.  It’s more complex.

There are two sets of virtues men should aspire to:  The “puppy” virtues and the “manly” virtues.

The “puppy” virtues are those stated above:  Loyalty, politeness, patience, empathy, thoughtfulness.  These can be performed by a small dog.  (And the dog probably does it better). 

The “manly” virtues, which are far less discussed and in far greater demand, are things like: Independence, confidence, capability, social acumen, humorousness, and ambition. 

To use an automotive analogy; think a romantic relationship as a Chevy Volt.  It operates on two power sources.  It uses a battery to start and go for about 50 miles.  After that a combustion engine needs to kick in.

The “manly” virtues are like the battery and electricity – these are necessary to get the car started and moving.  The car can even go for a while solely on that energy source… but only for a while. The “puppy” virtues are like the Volt’s combustion engine and gasoline.  These are needed to keep the thing running for meaningful distances.

A man who possesses the “puppy” virtues but lacks the “manly” virtues becomes a “nice guy” – and remains perpetually single.  He can’t get the Volt started.  He’s good for friendship, and that’s it.

A man who possesses the “manly” virtues but lacks the “puppy” virtues becomes a jerk.  He will have multiple short-lived relationships, but can’t sustain them because he’s intolerable.

Lesson for Guys: Don’t try to be the perfect nice guy.  Develop both sets of virtues and become and impressive man.  As I like to say; “Think Han Solo and not Luke Skywalker.”

Lesson for Gals: Think about the virtues of the guys you’re dating.  No one is saying you have to settle for a “nice guy”.  But being more discerning can help you avoid the jerks.



Rule #5:  Beware the “Inverted Triangle of Despair”.

A question:  If a girl has a choice between a “nice guy” and a jerk, who does she go with?

(It is a trick question)

The answer is both.

Officially she dates the jerk, because he’s the more interesting of the two.  But what does she do whenever the jerk does some manner of jackassery?  Well, she calls up the “nice guy” (who is always there for her) and commiserates about her jerk boyfriend.

This actually forms a stable triad.  The jerk is fulfilled because he has the girlfriend.  The girl is fulfilled because she has the interesting boyfriend and the emotional support required for putting up with him.

The “nice guy” is unfulfilled, but he’s willing to stick around because he’s perpetually reassuring himself that eventually the girl will wise up, drop the jerk, and come around to himself.  But in truth, no such thing will occur.  His continued emotional support is actually enabling the girl to stay in this bad relationship.

Lesson for Guys:   If you find yourself being used as an emotional support – (and you are being used) – get out of it.  The only person you’re helping is the jerk boyfriend.  Say something like:

“I don’t get why you’re dating this jerk, but its not my business.  I don’t want to talk about your relationship issues.  You have girlfriends for this.  Not me.” 

Lesson for Gals:  If you’re dating a fella who requires you to use another guy for emotional support … you’re dating a jerk and taking advantage of a nice guy.  Stop that.



Suggestion 6:  Strike while the iron is hot.

One question a lot of guys wrestle with is: “When do I ask the girl out?”

A common answer goes like this:

“First you become friends.  Then you become better friends.  Then maybe you’ll notice some mutual attraction.  Now you can ask her out.”

That CAN happen, but many times it instead goes like this:

“First you become friends.  Then you become better friends.  Then you ask her out and she says, ‘I don’t want to ruin our friendship’.”

In the first sequence of events the friendship a staircase to something more.  In the second sequence – (which I think is more often the case) - its an insurmountable obstacle.

What happened in the second case?  Well, the guy became part of her mental furniture.  He was a comfy sofa, and then he approached her asking to be a love seat.  But she liked the sofa, and she's not sure about this brand of love seat.  She doesn’t want the sofa to change.

So her response is basically, “I want things to stay the same.”  Which, to be fair, is what she genuinely wants.  She can’t simply –decide- to have affections for the guy after becoming accustomed to him as a friend.

But at the same time the guy can’t simply –decide- to stop having feelings for her.   A “yes” or “no” would have satisfied him, but instead he’s sent away being told that his GREAT JORB as sofa is the very reason why he can’t be something more... which is maddening.

Lesson for Guys:  You might notice that the girl you’re interested has started going out with some guy she just recently met.  Why?  Because she had no opportunity cost in doing so.  It didn’t require her to change or lose any of her existing relationships.  This is no accident.  And in my estimation, it’s why the appropriate time to ask out the girl is immediately after the first impression.

You likely knew from the beginning you were interested, so make a good impression and immediately follow up.  Let the chips fall where they may.

[On a side note, the father of one of my students had an interesting response when told “I just want to be friends.”  He told her flat-out, “That’s not an option.  It’s ‘yes’ or ‘no’.  I don’t want to just be your friend.”  Today they’re married.  Food for thought.]

Lesson for Gals:  When the guy-friend suddenly asks you out, don’t work your appreciation of the current friendship into your decision.  And certainly don’t cite it as an excuse for saying "no". 

Look, the friendship ended as soon as he realized he wanted something more.  There is no “undo” or “cancel” button he can hit.  So it makes no sense to reply:

 “I liked the sofa and don’t want to risk losing it” 

… because you’re losing the sofa either way.  Staying the same isn't on the table.  Because even if he ostensibly goes back to his role as "just a friend", his unrequited interest in you will always be gnawing at the back of his mind. 

The choice at hand is whether to have the guy as a boyfriend.  It's your right to make that choice, but as we saw in Rule 1, don't make excuses.  Be clear.

Let No Root of Bitterness...: 

The letter to the Hebrews states:

"Pursue peace with all people, and holiness, without which no one will see the Lord: looking carefully lest anyone fall short of the grace of God; lest any root of bitterness springing up cause trouble, and by this many become defiled." - Hebrews 12:15

One might say the rules (and suggestion) above reflect the mind of a bitter and cynical man.  But in truth, I didn't articulate these rules until after I was happily married.  It was only after a great deal of reflection that I saw the patterns which so often lead to bitterness. 

So I like to these rules are ways to prevent oneself from becoming bitter and cynical.  The goal of dating is to find one's spouse and hand over your whole heart.  And by avoiding the pitfalls mentioned above, one can better ensure it is delivered intact.