Chris’s 3 Rules of Dating

At BayCon, Chris revealed his three rules of dating, which contained enough insight and resonance that we later pressed him to post them for posterity. And after reviewing his expanded version, I have come to the conclusion that they're just as relevant to one's work life as one's love life.

Since I think these are pure brilliance and don't want anyone to miss them just because they're too lazy to follow a link, I'll reprint them here:

Chris's 3 Rules of Dating

I developed these some years back and several people asked me to write them down for them so here goes. Will they work for you? Maybe. I am reasonably confident that they worked for me given the beautiful, competent and intelligent woman I wound up marrying (see Poeso)!

Any set of rules/guidelines should be as succinct and unambiguous as possible which necesitates them being broadly worded. It also means that there are clarifications for specific points (in case you didn't catch the obvious intent) I have included a few. Finally, like Asimov's Laws of Robotics, these rules are in an order for a good reason...

Rule #1: Be comfortable with yourself! If you can't be comfortable with yourself then other probably can't be either. Being comfortable includes being comfortable around people you don't know or by yourself. Don't always rely on the opinions of others. In the end, it is your opinion of yourself that matters. Don't mistake Arrogance for Confidence. The Arrogant need other people to be wrong so that they can be right which builds in weakness. The Confident recognize that there are many viewpoints that can be right and refines their viewpoints by allowing them to be challenged.

Rule #2: Meet new people. There are many people in the world who can be "right" for you. The more people you interact with the more likely you are to meet one of them. Just because someone appears to be "right" doesn't mean that they are not already taken or will ever be emotionally available to you. Take heart, enjoy your time with them and LEARN what a "right" person looks like and looks for. The worst that can happen is you get a cool new friend and maybe learn something about yourself. Sometimes meeting new people means expanding upon the relationships you already have. "Friend of a friend" is more likely to have common interests and come to you "pre vetted" by the people you already trust. Make time for the people who make you feel good about yourself. Who knows, one of the cool friends you have may have been waiting for you to become "emotionally available" and you may not have noticed it. Either way, it helps with Rule #1.

Rule #3: Avoid worthless relationships! Admit it, everyone has gotten into or stayed in a relationship that is just not fulfilling and never will be. Sex, routine, emotional security, what ever the reason in the end all you are doing is keeping yourself from growing as a person. Either work to improve the relationship you are in or get out! Grow or leave. Harsh, but this is the biggest trap most people fall in to: staying in a dead end relationship because they lack the confidence to either make it work or end it. If you are not yet in a relationship, remember rule #1, enjoy being with yourself. You don't need to get hooked up just to validate your self image. Flirt, have fun, be daring, but don't date some one unless you see in them the qualities that make you say "wow, I'd be really happy to tell my friends I am dating this person"


  1. Good rules, all!

    My own variations are as follows:

    “Get to know people as people, not merely as potential dating partners.” Takes off the pressure, leads to more friendships and can result in dates.

    “Avoid traits you know are unappealing and accept everything/everyone else.” Once I stopped hunting for the “right” person and realized that anyone who didn’t have traits I found unappealing (for example: smoking) is someone I’d like to get to know (see above), I became much more comfortable with the social dynamic.

    Rule #3 is spot on. “No matter how you measure it, a bad relationship always costs more than no relationship.” Among other things, people who might find you attractive will see the relationship you are in and even if they are polyamorous, they might exclude you from their dating pool because you are willing to do things to have a relationship that turns them off.

  2. …don’t date some one unless you see in them the qualities that make you say “wow, I’d be really happy to tell my friends I am dating this person”

    This one is so. True.

    I wish I’d known years ago that if I don’t feel proud of the person I’m with, then there’s no respect and the whole thing is doomed.

    Live and learn.

  3. Wow, a nice way of putting into words my current philosophy.

    Take heart, enjoy your time with them and LEARN what a “right” person looks like and looks for.

    is a great way of explaining so many of my friendships and why I’m such close friends with so many married men. Yes, they’re taken, and I have no intention of going for them, but it’s nice to observe someone who might have been right for me and the way he behaves in a relationship, so I can know better what to look for in someone who is available.

    And I’ve totally given up on mercy dates. I’ve learned that I have never ended up liking someone more after getting to know him if I’ve been initially uncomfortable/unimpressed with him (usually, it’s quite the opposite), so if my instinctive reaction is a shudder, I don’t waste his or my time.

    • Good points all.

      Thanks for getting your friend to post this. I’ll have to copy it down. It would come in handy if the Dating for Fanboys panel gets resurrected. And before you laugh, unless I’m mistaken, there’s more than one panelist in this comment thread.

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