When I first started this blog over a year ago, I brainstormed an initial list of topics to write about.  One such topic is the “rules” of dating – The O-HI-30 Dating Rulebook, if you will.  The topic has been on my mind a lot lately, as I begin to re-enter the world of dating for the first time in eight months (an eternity for me).

What makes me an enough of an authority on dating to write a rulebook, you ask?  Well, for one, I’ve dated – a lot.  In fact, I’d be willing to bet that I’ve dated more than most of my friends combined.  When you’re single and actively trying not to be for as long as I have, you rack up quite a large number of first, second, and third dates.  Sometimes even a fourth.  And as frustrating and exhausting as all this dating can be, it has taught me a thing or two about how to date.

Now before you go lecture me about how there are no rules, or how these rules are keeping me from finding my one true love, hear me out.  When I first started dating, mostly after college, I obsessed about everything – whether I should go on a second date with someone I wasn’t into, whether he was into me, whether I should text him, whether I said the “wrong” thing.  It was exhausting.  But almost ten years and many many many dates later, I’ve finally become comfortable enough to (mostly) stop obsessing.  I’ve connected the dots, noticed patterns, and yes – have developed some “rules” to date by.  Of course these rules aren’t scientific, and they aren’t absolute. But they have helped my Type A personality feel more in control.  And when I feel in control, I can actually relax and enjoy the process – and isn’t that what dating, and life, is all about?

The O-HI-30 Dating Rulebook

1.  A Date is Just One Date
I still remember my first date clearly.  It was a late summer Thursday night, pouring rain, and I was supposed to be meeting this guy for the first time at a nearby bar.  Despite the fact that I had certainly been on dates before, I was sick to my stomach with nervousness.  This was my first true “blind” date – with a guy I had yet to meet in person.  I even remember calling my parents, near tears, saying how much I didn’t want to go.  But I’m not a flake, and I was not about to leave the poor guy hanging, so I sucked it up and went on the date (and although the date was just OK, I also went on a second date – see Rule #3).

Since then, I’ve been on a thousand first dates (an exaggeration, yes, but not that far off), and I’ve learned the invaluable lesson that a date is no big deal.  It’s just one date!  The worst date of my life lasted 45 torturous minutes, but I survived, and so can you.  The lesson here:  never turn down the opportunity to meet someone.  At worst, you’ll lose 45 minutes of your life and have a good story from it.  And at best, you’ll meet him.  One date never killed anyone!

2. And Two Dates is Not Marriage
To go on a second date or not to go on a second date – that is the question.  I have wasted hours of emotional energy obsessing over whether or not to go on a second date with someone I was just lukewarm about.  When I was younger, if a guy asked me out on date #2 (and to be honest – they almost always do – I’m good at the first few dates, just haven’t figured out how to make it last!), I said yes 99% of the time.  I listened to the voices in my head (and of those around me) that said, “give it a chance, he might have just been nervous, you can’t really know if you are interested in someone after one date” etc. etc.  Every once and a while, those voices ended up being right – I did warm up to the guy on the second date.  But most of the time, the second date validated that I was Just Not That Into Him.

The key here is that if you are unsure about someone after the first date, then go on a second.  Two dates doesn’t mean you have to marry the person.  But that second date probably will be enough to indicate if you want to move forward with him, or move on to the next one (as Jay Z would say).

3. If You’d Rather Be Home Watching TV, it’s Probably Time to Move On
So let’s say you went on that second date, and now you’re questioning whether to go on a third.  I’ve been in that place plenty of times.  One of those times, I was telling my Mom that on my second date with a particular fellow, I kept sneaking looks at my watch; despite my best efforts to be engaged in the conversation, time was dragging.  Her response?  “Dating is supposed to be fun!  If you’d rather be home alone watching TV or reading a book, then you’re probably not into him.”  What simple and priceless advice!  If I’m looking at my watch or wondering when I can get home to curl up on the couch with my cat and latest episode of Orange is the New Black (season 3 starts Friday!), it’s probably time to move on.

4.  It’s OK to Say No Thanks
One of the joys of having dated a lot is that I finally can tell whether someone is going to be a possibility after one date (note that I say AFTER one date; see #1).  This might sound contradictory to Rule #2 – go out with him again if you are unsure.  The key phrase there is if you are unsure.  When I was 25, I often wasn’t sure how I felt about a guy after one date.  I needed to go on a second (or third, or fourth) to find out.  But now that I’m 31, I don’t have to go on multiple dates to figure that out. Experience has given me the ability to know much faster whether I’m into a guy or not.

Now before you go and say I’m “being too picky” or “too quick to judge”, hear me out.  It’s not about whether he wears bad shoes, or picks a bad place to meet for a drink, or doesn’t hold the door open for me.  But if I don’t laugh easily during the date, or he shows very little interest in me while I’m speaking (something that happens more often than it should), or has a raging hatred of Hillary Clinton, or only dines at chain restaurants, he’s probably not the guy for me.  It’s OK to Say No Thanks.

5.  But Always Say No Thanks
So you’ve navigated Rules #1-4, and you’ve decided you don’t want to go on another date with this person.  What do you do now?  If you’re a guy, the answer is pretty simple – don’t ask the girl out again, and she’ll get the idea.  But if you’re a girl, you unfortunately are more likely on the receiving end of that situation (see Rule #6).  Do you owe him a response?  Most people I know would say that if you’ve been on less than two or three dates with someone, you don’t.  You can simply “disappear” – aka, never reply to their last text.  But I’m not most people.

It might seem outdated, but I subscribe to the childhood lesson of, “treat others like you want to be treated”.   Putting myself in the guy’s shoes, if I asked a girl out, I’d expect a response – even if it was a “no”.  Simply put, disappearing just isn’t very polite.  If a guy does ask you out again, and you aren’t interested, a simple, “thank you, but I just don’t think it’s going to work for me” is straightforward and effective.  There is no confusion, the guy isn’t left wondering why he never heard from you, and you can move on.  The same goes for guys; if you’ve been dating a girl for a little while (read: more than three or four dates), it’s nice to let her know that you’ll be moving on.  After a handful of dates, disappearing is kind of rude, not to mention lame.  It’s OK to Say No Thanks, But Always Say No Thanks.

6.  Men Like to Think They are In Charge
This one is near and dear to my heart.  I would argue that I have more “balls” than most men I know.  Just ask my friends – I’ve asked many a man out!  Naturally, this assertiveness carries past the first date – I’m impatient, I want the guy to ask me out again, and on my terms.  I want to kiss the guy.  If I don’t hear from him after the first or second date, I want to ask him out – why does it always get to be his decision?

But here’s the reality:  men like to think they are in charge.  Don’t listen to what others tell you – gender stereotypes are still holding strong.  In my experience, if a guy hasn’t asked me out on a second or third date, it’s because he doesn’t want to go on a second or a third date.  Or if he hasn’t kissed me, it’s because he doesn’t want to kiss me (at least not yet).  Me making the move rarely helps – trust me, I’ve tried.  Men enjoy a chase.  Playing hard to get – just a little – is highly effective.  Note that I’m not saying men like to “be” in charge – in fact, much of the time the woman actually has the upper hand.  The man just likes to think he’s in charge.  So let the guy think he has the upper hand (even if you do), play it cool, and see what happens.  You’ll reap the benefits.

7.  Less is More
One of the observations that makes me most frustrated about dating is that women have the reputation for being “crazy”.  In my experience, men are often the “crazy” ones.  They ask you a million questions before they’ve even met you (all via text), they text you immediately after your first date saying how much fun they had and that they’d like to see you again, they want to see pictures of you in a dress that you just bought at the mall.  They tell you “good night” and “good morning” every day as if they’re your boyfriend, when in actuality you’ve only been on one date.  Can you say intense?  In short, they come on too strong.

In my opinion, in the beginning of a relationship, less is more.  I don’t need to hear from you much (if at all) between our first and second date.  I don’t need to know how your day was, or tell you how mine was.  A little bit of mystery is intriguing.  We both have busy, exciting lives, and we’re just making a little room for the possibility of a relationship.  Of course, as that relationship builds, breaking down those walls and showing some vulnerability is a good thing.  But until that happens – less is more.

8.  People Move at Different Paces
In Rule #3, I shared some advice my Mom gave me years ago.  But it’s not just my Mom who gives good dating advice.  In fact, my Dad would argue that as a man, he is in a better position to give me dating advice than my mother or any other woman.  And you know what?  His advice is usually spot on.  One piece of advice that has stuck with me is something he told me my sophomore year of college, when I was dating a guy from my Mechanical Engineering class (he wooed me with his knowledge of dynamics).  I was obsessing to my Dad about something, and he told me, “people move at difference paces.”  That just because I was really into the guy at that moment, didn’t mean the guy was really into me at that moment.  But it also didn’t mean that he never would be – it just might be at a different moment.

Relationships are up and down, and people move at different paces, which is why it’s even more important to keep Rule #7 in mind.  Since you don’t know at what pace the other person is moving in the early stages of a relationship, less is more.  Don’t overwhelm someone or push them to move faster just because you are moving faster.  That being said, you have to trust your gut.  I’ve often confused “he’s just not that into you” with “moving at different paces”.  If your gut is telling you a guy just isn’t that into you – and probably isn’t going to be – you’re likely right.

9. It’s Never the Same Twice
This is a tough one, particularly coming off of a great relationship.  It’s so easy to compare every date to the one before it.  “With guy X, I felt something right away”.  “Guy Y picked the perfect first date place”.  But this line of thinking sets us up for disappoint.  Every relationship with every guy is going to be different.  They aren’t going to do things the same way.  And thank goodness for that!  How boring dating would be if they all did.

I almost titled this Rule “He Can’t Read Your Mind”.  Because not only is dating going to be different with each guy, each guy also cannot read your mind.  Just because you think a great second date place is dinner at XYZ place doesn’t mean that’s what he has in mind.  I’ve often found myself thinking, “he picked THAT place for our second date?!”, only to have a fantastic time – and vice versa.  And again, because Rule #6 tells us that guys like to be charge, you can’t squash his date suggestion just because it’s not exactly what you had in mind.  Every guy is different, but none of them can read your mind, and most of them are clueless anyway.  So go easy on ’em.

10.  When It’s Right, There are No Rules
I’ve saved the best for last.  It might sound cliche, but when it’s right, there really are no rules.  In my last relationship, Rules #6, 7, and 8 were all broken (at least to an extent).  I did follow his lead, but I didn’t hold back or play hard-to-get.  He was interested, I was too, and there were zero games. Not once did I obsess about whether or not I should text him, or what I should say in that text.  I knew that none of it mattered – he was into me, and one stupid text wasn’t going to change that.  We were all-in, right away.  It was so refreshing.

I’m confident that I’ll find him again – a guy that makes all the Rules obsolete.  But until then, this Rulebook provides my Type-A personality with a sense of control and a plan for navigating the scary world of dating.  So next time you find yourself or a friend in a dating conundrum – consult the O-HI-30 Dating Rulebook!

Have a rule I forgot to include?  Disagree with one of mine?  Tell me!





  1. Okay… there are so many things I’d like to say: you are my daughter (say, I recognize 50% of the gene pool belonging to me), you far exceeded my dating experience level (can’t believe I say this – but it’s true), you even provide more factual user guide than your 4th (or 5th?) cousin who wrote a whole book on dating and made millions of it (really, true!), and finally – you are one completely amazing person, and someone will one day will be lucky enough! (and I hope I will like him like you will…).

  2. This is simply an amazing read. Wow.

    A couple of suggestion for you Dad:
    1. can’t you come up with a math algorithm that simplified the 10 rules above into a couple of lines?
    2. even better, why not one of your patented blood tests?

  3. I agree with Yossi, amazing read. But, rather than an algorithm, throw out rules 1-9 and go with #10. Enough with uncles and fathers.

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