Resources: 10 Dating Guidelines

From a gal who went on her first date in fifth grade (the movie Gremlins, we did not hold hands, which was our only goal) and met her husband at age 38.

These are dating guidelines acquired over many years of experience.  Many years of gathering data not just about the other gender (in my case men but hopefully that doesn’t limit the usefulness of this to all genders), but my own actions, reactions, mindsets and moods in relation to the specific ritual of dating and courting.  We are all both at our best and at our worst in this ritual; our best in that we present our best selves; our prettiest most manicured selves as well as our best behaved, most appealing selves.  Our worst in that our egos are on display in precarious ways, our insecurities and sensitivities become magnified and our judgement gets blurred by all sorts of things; fear of rejection, loneliness, boredom, desire, need, hope…all very human feelings for which we forgive ourselves more easily when there isn’t another human we don’t know very well reflecting them back to and on us.

Which leads me to my primary guideline in dating, which is to be kind.

Guideline #1:   Be Kind

First and foremost, be kind to yourself.    You will likely make a few less than ideal choices.  And then you will make them again.  I don’t know why exactly—we all make our questionable choices for our own unique reasons, but we seem to be especially prone to questionable choices while dating.  It’s just too easy to make a regretful decision in this crazy dynamic where it feels like there is a magnifying glass on you. You are trying to be nice, to be open, to be accepting, to be non-judgmental, to be authentic, not too crazy, not too rigid—there’s just way too much GOING ON to be in the place you make all your wisest choices from.  So be kind.  Forgive yourself.  Just do your best.  Maybe you’ll date an asshole for a little too long.  Maybe you’ll run scared from a really nice person.  Maybe you’ll be too mean or too nice or too fake or too pushy.  Maybe you’ll sleep with someone you wish you hadn’t slept with. Note it, ask yourself why and use it to do something differently next time.  But don’t punish yourself or judge yourself too harshly because it makes the game too long and hard.  If every screw up is a reflection of who you are, it will be too hard.  It’s just a behavior that something about that person or dynamic brought out in you.  Look at it, tell a friend about it over a beverage and move on.  If we are kind to ourselves, we can learn from everything we do.  If we are judging ourselves, it’s harder to believe we can do something different next time.

Secondly, be kind to them.  We have a tendency to over exaggerate someone’s deficiencies and faults if they are not a match for us. But of course, most people are not a match for us.  For 101 reasons.  The whole thing becomes more fun when you can have a date and recognize, “that person isn’t for me” without needing to turn them into a villain and do a breakdown of everything wrong with them. I met a lot of guys who weren’t for me.  I had some nice dates with them, not super exciting perhaps, but nice.   I also over demonized some guys.  Probably because I thought I really liked them and then as I realized it wasn’t a good fit, the disappointment made me want to vilify them.  There’s not a lot to gain from this because part of us knows we are just tricking ourselves into being less disappointed.  I found it a better practice to be realistic about what the qualities were that made us incompatible rather than simply trying to figure out why he was an asshole.  And realistically figuring out what didn’t work between us helped me better figure out what I was ultimately looking for.

Of course every once in a while we do encounter someone who is simply self-involved and unkind and it’s important to be able to recognize this and move on quickly. If you suspect you are in a pattern of being drawn to un-kind people, do get help.  Give your friends permission to call it how they see it, including that you are letting yourself be treated badly.  There are 7 billion people on this planet.  Please don’t choose one who is un-kind to you.

Guideline #2:   “Rejection” is mostly a Gift

Sometimes they will figure out why you aren’t compatible before you do.  This is what feels like rejection.  But it’s only sort of a rejection, because there’s an incredibly good chance that if they didn’t figure it out first, you would eventually.  Again, a thing that I found very comforting even though daunting is that most of my dates wouldn’t be right for me over the long haul.  I am not compatible with most people.  Neither are you.

A related anecdote: I remember a couple of guys I quite liked but it was clear pretty early on that my directness, openness and candor made them uncomfortable.  I remember them flinching a bit when I’d initiate a candid conversation in public, challenge someone’s thinking or speak openly about something they perceived to be more discreet.  There were enough areas of compatibility that it definitely hurt my feelings when I felt them backing away.  I probably would’ve given us more of a chance –a few more dates to see if we could meet in the middle.  In retrospect though, there would’ve been no point in this, it just would’ve made things more difficult.  Their backing away was a gift.  Those qualities are essential to who I am.  In one relationship, I tried to stifle them to make us work and it was really unhealthy and painful.  Plenty of guys I dated loved those qualities in me.  My husband relies on them in me.  He appreciates and admires that directness and candor.  He loves me for the qualities that most define me-the very ones that made others think again.   If someone you like backs away, it’s going to hurt for a minute.  It’s likely though that the path is being cleared for someone who will run towards you for those very same reasons that made someone else back away.

And related to that: Perhaps there are behaviors or qualities that are getting in your way.  We all find things we decide to modify and flex about ourselves over the course of our lives.  Our relationships with family, friends, colleagues, and partners expose tendencies which may not behoove us or serve our goals and desires.  Just be careful about over analyzing these behaviors when in casual dating scenarios.  Let people close to you help you determine if you have some self-sabotaging behavior or if something about you needs to be examined because it’s an obstacle to getting what you want. But don’t start turning yourself into a pretzel to meet some potential partner’s needs and wants.

Guideline #3: Be Realistic about the Numbers Game and Making Comparisons

The numbers are against you.  Accept and embrace this and let it take the pressure off.  There is a 1% chance you are a match with this person.  But there’s a really good chance you can have a nice conversation and learn a few things.

It’ easy to do a compare-a-thon with this one.  Well, but so and so found someone so quickly or but why is it taking me so much longer than everyone else.  And there may be some reflecting to do there.  Yet also, everyone is using different standards and looking for different things. For different levels of connection, being seen, comfort, chemistry, etc.  If you are going to compare your trajectory to others then you have to make sure they are measuring by all the same standards you are and that they are in the exact kind of relationship you want to be in.  For years, I was surrounded by people who had found their partners and were starting families while I was still single.  But I wasn’t surrounded by people who were in the exact kinds of relationships I wanted to be in and who were beaming with unfettered joy and satisfaction.  If you are prone to comparing yourself or your situation to others, this distinction matters…look closely…make sure you are not measuring where you are against relationship labels and ideals and Instagram pictures…it’s a false comparison.

Guideline #4:   Keep Your Side of the Street Clean

This one is a little tricky, but it really helped me: Behave from the place of being treated as you want to be treated.

In the early stages of dating someone, we quickly find ourselves in the dynamic of over-analyzing their behaviors and actions.  Why didn’t they text? Why did they text instead of call? Isn’t that a jerk move to cancel at the last minute!? That doesn’t seem like a very good explanation for being late–should I believe it?… and so on.   Then our behavior towards them shifts because we are put off by something they have done or said or not done or not said.  We become a little colder or we don’t call them back when we really want to; we adjust our behavior to match the deficiencies we feel in theirs.  If they are a jerk, we are a jerk too.  If they wait forever to return a text, we wait slightly longer than forever, just to show them we’re not desperate. To show them that I also have an important life that takes precedent over you and even though what I want more than anything is to be gazing into your eyes in the corner of a dark bar tonight, there’s no frickin’ way I’m going to reveal this with the frequency or timeliness of my texts.  And THEN when there’s no date at all that night, you don’t know if it’s because of him or you. When you are trying to break down what is happening or why they are behaving a certain way, you have to factor in your own questionable behavior. Well, maybe if I’d called when I said I would, or maybe if I hadn’t scolded them for doing that thing or maybe if I’d let them know I wanted to see them instead of playing it cool, they would’ve been nicer or done that differently.  And then we are in a web of both of us behaving not quite how we want to be behaving and we can’t separate out their actions from their reactions to what we’re doing.  When this happens, our insecurities are running the show.  Our insecurities never represent our best selves.

One of my best dating practices that evolved over years of this insanity was that I kept my side of the street clean.  I behaved how I knew I should behave and how I wanted him to behave.  Sort of like the golden rule—I treated him how I wanted to be treated even if he wasn’t treating me that way.  Because it eliminated a lot of drama and sped up my ability to recognize who I was dealing with.  If I responded to him being late or lacking transparency without being accusatory, then his defenses weren’t up and we got a more authentic interaction.  I started out by giving him the benefit of the doubt and communicated in a way that I would want to be communicated with no matter what I was getting from him.  This made it VERY EASY for me to assess that his questionable behavior or communication skills were about him and not me.

Obviously as things progress, things get more complicated.  But it’s actually pretty easy to keep your side of the street clean for the first couple months.

Guideline # 5: Take Control of Your Dating Mechanisms

If you are using an app or dating website, make it work for you.  I don’t know exactly how things work these days with the swiping left and right, but to whatever extent you can, take ownership of the experience.  Don’t be in response mode hoping the right people or algorithm find you.  When I was on, I ignored their suggestions entirely.  Who the hell cares that guy also plays tennis and has brothers??  I also rarely responded to the guys that reached out to me unless they were particularly thoughtful in the way they reached out.  I looked up people’s profiles and reached out to them.  We communicated a bit before meeting so I knew there was some level of substance there first.  That’s what mattered to me.  You may love the unknowns of a first encounter and that’s great. I’m just saying don’t let the mechanisms of the dating app put you into response mode or waiting for validation mode.  Figure out how to make it work for you to increase your sense of agency and the number of people you are likely to enjoy having a drink with.

Guideline #6:   Re-orient When Weary

If you find yourself growing weary or taking everything too seriously, including yourself, re-orient yourself towards dating for a bit.  Consider yourself an anthropologist doing research.  Ask different questions than usual, try different ways of responding just for fun to see what happens.  Watch Sex and the City and go on your date knowing that if nothing else, you can gather entertaining material for dinner with your friends.  I’m not saying to do something like this all the time.  Obviously we want to bring who we really are to the table and we don’t want to waste anyone’s time.  But for those of us that were/are in the game for a very long time, sometimes we need to shake it up.  It can get laborious and depressing and sometimes a little playful re-orientation towards the whole process can help us stay light and in the game.

Guideline #7: Take Breaks When Blue

If you are feeling beyond weary and downright shitty, take a break.  I have no memories of getting out there and dating making me feel better if I was in a dark place.   It’s hard to go to a group event when we’re down let alone to put ourselves out there for a date when we’re down.  The group thing has multiple components, variables and dynamics so if you are going to force yourself up and out, do the gathering–be with friends, share ideas, eat, play, etc.  But a date is all about you and one other person and you being reflected back at you.  If you aren’t liking yourself at the moment, it’s not likely to be a great experience.   I took lots of breaks.  Focused on something else–work, friends, soul searching.  I knew in my gut I wasn’t going to be a very good version of myself and so wouldn’t attract or be available to the right people. Then I’d wake up one day and feel like going on a date.  I’d just be ready for the adventure of it.  And for the most part, when I was feeling adventurous, I had tons of fun dating.   Even when there were a lot of busts, I still had fun diving into the dating dynamic and giggling with my girlfriends about it.

Guideline #8:   Be Aware of First Date Haze

Try to refrain from too much forward-looking excitement until at least Date #2.   Not that you shouldn’t enjoy every moment and feeling of glee that comes from a great first date.  By all means, dig into the moment.  But I learned that there’s a magic haze over a lot of first dates.  It’s easy for both of us to be curious and fascinated when everything is brand new; we like them and we like ourselves for being so very curious and fascinated. The stories of us and them are at their best, the energy is unfettered by anything beyond first impressions.  I had enough amazing first dates that led to shockingly disappointing second dates that I thought it was worth a mention.  That way you can be extra pleasantly surprised if some of the first date magic carries over into the next few.


The hazard, beyond the deep disappointment of the dynamic being so very different than we’d initially thought, is that sometimes we might be so attached to who this person was on Date #1 that we stick around for too long waiting for that person to show up again.  I’m thinking back to a couple instances where I went out with someone on four or five increasingly bad dates, despite all my instincts screaming “no way!” because I was so attached to who I’d thought he was on that first date.

Guideline #9:   Chemistry Usually Shows Up in the Beginning

I’m sure that you can find some people who found chemistry with people they were initially just friends with.   And I’m sure that you might know some people who didn’t feel any attraction at first, but later, after trust was built and they realized how much they liked someone, the chemistry arrived.  Those stories and instances definitely exist. I just want to say, since these are my guidelines, that this never happened to me or anyone I know.  The chemistry was there from the beginning or it wasn’t.  Lots of instances where there was plenty of chemistry but questionable substance.  Some instances of some attraction that turned into more attraction as the intimacy increased.  But no examples of zero attraction turning into a lusty, fulfilling relationship.  I had two instances of wishing very much this could happen because I’d met such lovely guys.  I waited for the pitter patter for quite a long time with one of them.  It never came.  Just putting that out there for whatever it’s worth.

Guideline #10: Know the Difference between Red Flags and “Flipsides of Coins”

There are “red flags” and there are what I call “flipside of coins.”   Red flags, as most of us know, are early indicators of what will likely become issues or deal breakers.  So there’s some really good stuff between you, but some nagging behaviors: they are always late or don’t ask many questions or are hyper critical of people.  The things we decide to keep an eye on because our experience and instinct know the tips of icebergs when we see them.  Flipside of the coins are the less desirable behaviors or qualities that generally come alongside of qualities that we really value or appreciate.  So if I love that someone is super ambitious and successful, the flip side of coin is that the source of that ambition will take a lot of their time and attention—often over me or other things I value.  If I love that someone is deep and thoughtful about things, it may mean that they also have a tendency to want to talk about and over analyze even simple situations.  If I love and value that someone is organized and efficient it might mean they get cranky with me if I want to be relaxed or non-committal about something.  It’s important to recognize flip side of coins because as we seek the qualities we most value, we should know the flipside of coins they come with.  We can get better at differentiating early red flags from things that may well be flipside of coins for the things we most seek and value.

Please remember that these are guidelines, not rules.

They come from my experience and that of my community, no grander place—there’s no validated research.  They do come from my heart.  From a place of knowing how tender we can be in this human ritual and wanting it to be more fun and fulfilling than stressful and depleting.  If they don’t resonate, throw them away and go do your thing and have fun.  If some of them do, mull around with those ones and leave the rest.  Much like dating itself, we take on what makes us better, and leave the rest for someone else to explore.