Dating is not Simple

I still talk about dating a fair amount with my friends. We compare notes. We make lists. And whatever our discussion–comparing paid dating sites to free dating sites, considering the virtues and difficulties of meeting people in person instead, considering what traits in a partner are essential and which simply icing, contemplating profile photos–we always tend to hit on one consistent idea: that dating can be really freaking difficult.

There’s this sense of indignation about the whole thing, this semi-random process that is supposed to help you discover this compatible someone. It seems so inefficient! It seems so random! It’s painful to be rejected and it’s painful to be doing the rejecting.

But then I think about what many of us want dating to achieve–to find a life partner–and I’m not surprised it feels complicated and difficult. I am almost more surprised it works at all. It feels like a tall order.

Ferrett wrote a great post about dating last month–The Abandonment Rate, Or: Date More, God, Date More–in which he said:

It took me fifteen years of constant dating before I found the love of my life, and I consider that to be a pretty lucky catch. You? You’re trying for life-changing things. That’s good. Life-changing things involve a lot of perseverance. So keep at it.”

Fifteen years? That’s a fair amount of effort.

My friend has this theory that it is important to know the three things you most want in a partner. It can only be three, and it includes everything from personality traits to likes and dislikes to basic life information. Only three! I was skeptical, but it didn’t matter because I still had to figure out my three. I spent a lot of time coming up with and rejecting and ending up with more than three.

And now, I can’t even remember what I finally settled on. I’m fairly confident one of the three was kindness, but the other two…um….maybe intelligence? I don’t know. The whole exercise felt like boiling something complex down into something so simple it no longer held any meaning.

So then I wrote a list of what I was looking for in a partner, and I let myself write down as many items as I wanted. I put a lot of stuff I thought was important, but I also let myself put down things that seemed silly or trivial or like low-hanging fruit but I still wanted: things like “knows how to dress self for different occasions” (I live in Silicon Valley so this is an actual perk), “has an overlap with my musical taste,” and “not intimidated by Shakespeare.” (Yes, I really put those on my list.)  

I put 59 items on my list. Yes, fifty-nine. A far cry from three. But reading my list now, I keep nodding and saying, “Um, yeah, of course I want that. And that. And that.” It’s not that I felt I needed all 59 things to be perfectly true, and a bunch of them are low bars, but even so. I did want a majority of them.

59. Not really all that simple.

Strangely, I found making that list to be liberating. Because then dating did not have to be simple. It validated my actual experience, which was that finding someone compatible to date wasn’t that straightforward, that there was no algorithm that took all the guesswork out of the equation, that the only real way forward was to meet a bunch of people, and most of them wouldn’t be right, and that would be tiring, and all of this was perfectly normal.

I’m not saying there aren’t things you can do to simplify and streamline the process, or to improve your chances of success. But online dating sites sometimes make it seem like dating is straightforward shopping; you flip through a seemingly infinite catalog of biographies and jokes and photos, you are presented with an array of options, there are percentages and matching protocols that are supposed to help you narrow things down. All very clean until you hit the next part of the process: actually communicating with another human being, a person who can’t be completely boiled down in a few paragraphs and photos and multiple choice questions.


Looking for a life partner is anything but simple. You’re going to spend A LOT of time with this person. You’re going to make major life decisions with them. You’re going to be influenced by them. You’re going to get to know them very well, and they’re going to know you very well. Your life is going to be changed by being with them. And the process of dating is going to reflect the importance of this decision.

No list, whether of three or of fifty-nine, is ever going to be able to accurately reflect the reality of that decision. Instead we have to get our hands messy and do the work of getting to know other people, and maybe even more importantly, getting to know ourselves.

I write a lot about friendship.

A few days ago I saw someone share an article about friendship, and someone else responded to their post by saying that this was literally the first article about friendship they’d ever read. This made me feel good that I’m already writing about it, and also sad there is a relative dearth of information and thought about friendship out there.

When I write about boundaries and friendships, I know some of you are wondering what kinds of boundaries are common to need to set in the context of friendship. I think this varies a lot from person to person and from friendship to friendship, but I do have some general thoughts on what I look for in my friends and what kinds of boundaries sometimes come up.

Kinds of issues that come up in friendships that sometimes require boundary setting/enforcing:

  • Responding to invitations
  • Responding to favor requests
  • Having to cancel plans due to illness or emergency
  • Arranging logistics (including scheduling, timing, transport, choosing restaurants, choosing activities, issues of payment)
  • Addressing mobility/health issues
  • Asking for empathy instead of advice
  • Negotiating the flow of the house guest (either being one or hosting one)
  • Figuring out frequency of communication/visits, response time, safeguarding work time, etc.
  • Seeking safe spaces at public (or semi-public) events
  • Dealing with problematic behavior in communities and friend groups
  • Responding to sexual requests
  • Responding to peer pressure
  • Asking for and giving emotional support
  • Speaking up on issues of social justice
  • Asking for consideration
  • Taking someone into your confidence

I’ll be honest for you: I look for friends who don’t need much boundary enforcing because that’s the part I find the most difficult and tiring. I can often set a boundary now, especially if I have a little time to consider, but enforcing it against push-back wears me out extremely fast. And no wonder. Boundary enforcing means your boundary has already been crossed (or is not being taken seriously after being stated), and it often involves hurt feelings, or at the very least disappointment, especially if it’s a repetitive issue. So it’s much easier to reach a point of diminishing returns if you’re having to enforce regularly. (Also, one way of enforcing is to introduce space into the friendship, and if you have to introduce enough space, you’re not interacting much with that person anymore anyway, so selecting for low levels of enforcement tends to happen at least somewhat organically.)

I look for friends to whom I can say no. Sometimes that will be no to a favor, and sometimes that will be no to an invitation. In an ideal world, I could say yes to everything, but the reality is that I have lots of commitments to fulfill, as does any adult: in my case, to my work, to my own physical and mental well-being, to my dog, to my boyfriend, etc. I have idiosyncracies to work around for maximum well-being, like my general dislike of driving too much, especially in traffic, and my sleep issues. I have budgetary restraints. I get sick and injured. All of these things mean that sometimes I have to say no, and I look for friends who will understand that it’s not personal and that I would help them or hang out with them if I could.

I look for friends who will make a commensurate effort. This doesn’t have to be equal in an obvious sense: for example, I have friends who always come over to my place and other friends who I always visit at their places, and as long as everyone is cool with that, it works fine. But both people have to be willing to find time for each other and to care about how the other person is doing. And both people have to be getting some of their friendship needs met.

I look for friends who are generally kind. I used to think, oh, it’s okay if my friend is sort of an asshole, as long as they treat me well. But I’m not as on board with that line of thinking anymore because it’s so easy for that kind of behavior to eventually spread out to include you. Obviously no one is perfect, but I think kindness is probably the most important trait I look for in friends.

And in that vein, my closest friends are generally pretty good at empathy. I become closest to people with whom I can be honest and genuine about myself and my life without fear of judgment, with whom I can share openly and who will share openly with me, who can listen well, and where there is interest and care on both sides.

Finally, one of the great part about friendships I’ve learned while negotiating these things is that they can be flexible. They do not need to be all things, all at once. While my closest friendships are usually built on empathy, I also have great friendships based upon a shared interest (shocking, I know!) and great friendships based on compatible senses of humor. I have friends who I get to see one-on-one and friends that I almost always see in groups. I have friends who I talk to all the time and friends I only get to see once a year. I have friends who I don’t ask for certain things because I know they cannot give them to me, and I appreciate what they do bring to the friendship and ask for those other things elsewhere.

I used to think friendship came in one certain mold, but in learning the many ways friendship can present itself, I’ve found a lot more interest and connection with the world. I thought by setting boundaries I’d be limiting myself, but instead my boundaries allow me to be more present and more accepting of who my friends are.

Even myself. Maybe especially myself.

Oh look, it's my best doggie friend.

Oh look, it’s my best doggie friend.

Several months ago, a friend came up to me and said, “Hey, you know how you’re always writing about boundaries and stuff like that? I don’t really get what you’re talking about. That’s never come up in my life.” And I wasn’t surprised, because this friend has great boundaries and is one of my boundary role models, so boundary situations don’t come up very much in his life, and when they do, he doesn’t notice that’s what they are because he has healthy instincts and just, you know, sets boundaries and goes on with his life.

I remembered this conversation when I read the post The Asshole Filter, which is about how you can go about unconsciously arranging your life so you end up dealing with assholes a lot, even when you’re not an asshole yourself. (Warning: that post is yellow font on a purple background and causes my eyes some pain. It may or may not also cause your eyes pain. But it is super interesting.) Anyway, the post is mostly in the context of accidentally developing an asshole filter in an organizational context, but a lot of it is also true in an interpersonal context.

So, here is one way to unconsciously develop an asshole filter in your personal life:

You start out with poor skills at setting and enforcing personal boundaries, probably because your home life as a child was kind of dysfunctional.

Then, as an adult, you meet a random bunch of people. Some of these people are mostly great. Some of these people are mostly assholes. You might be starting out with a few assholes from childhood as well.

What happens next? Well, the assholes will be thrilled to know you. Meanwhile, some of the great people aren’t going to end up being very close to you because the fact you can’t set boundaries makes them uncomfortable. Others of the great people are going to watch you not dealing effectively with the assholes, and this is going to train them into acting more like assholes to you too, because they’re going to think that kind of behavior doesn’t bother you. Also, a lot of people are pretty great overall…except when they’re not met with firm boundaries, in which case everything gets really messy instead. (When boundaries aren’t clear, mess tends to result, even if all people involved are otherwise amazing.)

Finally, dealing with assholes takes up a lot of time and energy. A LOT. So you end up being exhausted all the time, and therefore you aren’t putting that time and energy into your relationships with the great people, because they don’t need that much maintenance, so they gradually drift away. And you become more and more tired, even while you keep making excuses for the bad behavior that seems to be becoming more prevalent and thinking that if you could only be more patient or more kind or more understanding or more [fill in the blank here], everything would improve drastically.

At some point, you maybe stop and look around you and realize your situation is really unfortunate. You might even realize the whole “it’s always all my fault and everything in the world is my responsibility” thing isn’t ever going to bear fruit. But at this point you are incredibly tired, and it kind of seems like everyone in the whole world sucks, or at the very least takes an awful lot of energy to deal with. All you want is to be less tired all of the time.

So then, acting in self-preservation, perhaps you begin to isolate yourself. Which, unfortunately, makes complete sense given the faulty assumptions the data seems to imply but is actually a terrible idea. Because then you are cutting off ways of ever figuring out that actually, there are some really great people out there. All you can see, at this point, are the assholes.

Dark night of the soul time.

Then, if you’re really lucky, the writing community steps up and shows you incontrovertible evidence that not everyone is an asshole. People are unexpectedly kind to you. You start working as hard as you can on learning how to set and enforce boundaries and begin building a community of people who care about you and are good for you.

And then your asshole filter starts working in the opposite direction, and life is infinitely better.

No assholes beyond this point. (Photo Credit: derekbruff via Compfight cc)

No assholes beyond this point. (Photo Credit: derekbruff via Compfight cc)

Gilmore Girls seems to have a reputation for being in a certain demographic. A very female demographic. Which is particuarly interesting because, according to Wikipedia, for its first four seasons (which I would argue are its strongest), it ranked first in the 18-25 demographic for women and second in the 18-25 demographic for men. Meaning, people really liked it regardless of gender.

That being said, one of my male friends was embarrassed to admit he’d watched and enjoyed the show. Another one scoffed at the idea of watching it because it has “girls” in the title, so it obviously wasn’t for him. I think maybe it has an (undeserved) reputation for being like a Lifetime movie, something that would only appeal to women (and yes, there are all kinds of problems with that statement).

Of course, this tension is not universal. There is also the guy I was dating last year who was watching through the series and would tell me his thoughts on the episodes. And the popular two-guy podcast Gilmore Guys, hosted by one guy who loves the show and one guy who had never seen it before.

I started watching Gilmore Girls for the first time several years after it had concluded, when I was in the process of getting a divorce. I loved it at that time, and will probably always love it, because the show centers around Lorelai Gilmore, a (off-and-on) single woman in her 30s (she’s 32 when the show starts and 39 when it ends) who is not mostly defined by her relationships with men. She is smart, she is stylish (sometimes), she is assertive, she is ambitious, she is very good at her job and eventually becomes a successful entrepreneur, and her most important relationship throughout the seven years of the show is not a romantic one with a man (although she has those too!) but with her daughter. And as a smart woman in my 30s who didn’t want to define myself primarily by my relationship to men, I found watching stories of this fictional woman’s life vastly reassuring.

But as I continued watching, I came to realize Gilmore Girls is more than just a reassuring reflection for me. It’s really funny! (In an absurd way, which is my favorite.) It’s a smart, witty, show with a fast pace, a quirky style, and tons of pop culture references. It brings its characters and its setting of the idealized but bizarre small town of Stars Hollow (which is a character in and of itself) into vivid being. And it happens to center around the lives of a mother and daughter.

gilmore girls still

Yesterday, I read Penelope Trunk saying, “Men don’t need to see themselves reflected back to themselves in a relationship. They need to see themselves reflected back as some sort of hero. Women want to see themselves reflected back as being competent in relationships.” She goes on to say this because most women want kids, and it won’t be relatable for them to watch other women putting a career before family.

One of the reasons I love Gilmore Girls is because, while what Ms. Trunk says may or may not be true on a wider scale (and if it is true, it’s because of what our society raises women to value, so if our pop culture changed, this truth would most likely change as well), I know that I personally love seeing myself reflected back as some sort of hero. Who wouldn’t like that? Why can’t I be a hero and care about my relationships all at the same time? And it is a joy to watch a female character in her 30s be so competent, successful at business, and with a full and fulfilling life.

Also, it’s great to see other people, including women, who aren’t super competent at relationships (which Lorelai patently is not). Not only does that provide much-needed drama to sustain a longer-running television series, but come on! Relationships are difficult. None of us is perfect at them. And it’s affirming to see that lack of perfection reflected back in our media. In her book Daring Greatly, Brene Brown says that feeling like we’re not alone and that our personal experience is relatable and not unique to us is very important for shame resilience. Which is one reason why what the media portrays (and does not portray) is so critical.

Ultimately I’d like to see all kinds of characters reflected as heroes in media: female and male and non-binary genders, white people and people of color, young people and old people, straight and gay and bi people, people who are the same as me and people who are different from me. I want to see people being great at relationships and I want to see people who are messing up at relationships. I want to see warm family connections and I want to see troubled ones. I don’t really want to see absolute perfection because flaws are what make characters–and more generally human beings–interesting and three-dimensional and who they really are.

So dislike Gilmore Girls all you want, but dislike it because of its flaws as a show: the mess of seasons six and seven, the way it’s depressing to watch Rory descend into the dystopia her mother had escaped a generation before, the inconsistencies of the world, the way it deals with economic and class privilege. Dislike it because you don’t like watching dysfunctional family relationships or because it’s not a show centered around mysteries or action or whatever genres really engage you.

But don’t dislike it because it’s a show for women. It’s not, no more than Sherlock or Star Trek are shows for men (to mention two other shows I really like).

It’s a show for everyone.

Sometimes I feel really lucky to be an artist.

Not that there aren’t drawbacks: the constant stream of rejection, the competitiveness, the consequences of being even a little bit in the public eye, the self-doubt, etc.

But I understand myself well enough to realize I need the constant challenges in order to remain enthusiastic and engaged in being alive. Some people don’t need constant challenges. They’ve figured out how to make their lives work, more or less, and they do those things without constantly striving for more, or better, or different. And they are often content.

Trying something new...in Bali.

Trying something new…in Bali.

I would get so bored. I feel like we’re not supposed to admit that, that boredom is a possibility or something we experience. Boredom feels like it belongs in the realm of childhood summers before kids became so over-scheduled. Boredom feels like something we’re no longer supposed to have the time or inclination for.

Well, however untrendy it is to admit this, in certain circumstances I get bored. I get bored when I’m just clocking it in. I get bored when I’m not fully engaged. I get bored when I’m not pushing myself or learning something or trying something new. I get bored when I’m not thinking all that much. I get bored when everything in my life feels very static.

I also get bored at traffic lights, and waiting for people who are late, and talking on the phone to banks and health insurance companies and phone companies.

Anyway, there are a lot of strategies for minimizing boredom, but being an artist is possibly my favorite. Because as an artist, I never feel any urge to settle. I never feel that I can stop pushing to get better or to do something different or innovative or risky. Whenever I’m working on a book, I’m always aware there will be a next book, and then another book after that. And who knows where I will get to go for those books! And I spend a lot of time thinking and brainstorming and problem solving and doing targeted practice.

It really does keep life very exciting.

Also, Margaret Atwood is going to turn seventy-six in November, and she just had a new novel come out. Which makes me feel quite optimistic about a future for me in which I keep writing more and more books and challenge myself in different ways and never have to stop being an artist and keeping myself engaged.

Being an artist actually reminds me to stay interested. You wouldn’t think I’d need any help with that, but it’s so easy to take the path of least resistance, even when that’s not what you really want. But I have this idea that it’s healthy as an artist to keep feeding your brain and your imagination, so I’m always looking for opportunities to do so. Which has the great side effect of keeping me engaged.

But while being an artist is my personal favorite strategy, there are many more. What are some of your strategies for fending off boredom and staying engaged?

I’ve always considered myself to be a brave person.

Not physically brave. And given that a sprained toe that is supposed to take two to three weeks to heal is for me taking three months and counting, you can maybe begin to see why. I’ve got a different risk/reward ratio going on there.

But emotionally brave, absolutely.

In college it was about a ten minute walk down to the music building from where I lived. I’d be trundling downhill to go to an audition, and I wasn’t the hot shit in the music department AT ALL, so I knew the odds of me getting anything were incredibly slim at best. And in my head, I’d think, “This is absolutely insane. Why am I doing this? I could just turn around right now and go home. That is a real option for me.” And then I’d think, “Yup. And now I’m going to audition, goddamnit.”

And I wouldn’t get the part, but it kind of didn’t matter because I’d won just by showing up prepared and doing my thing. (It also kind of did matter, but after a while you get used to rejection so that it’s just this normal crappy thing that happens a lot.)

It actually became a point of pride for me, that if something made me frightened (except for physical things because I also care about self-preservation), I would make myself do it.

Recently, someone pointed out that often bravery is an action of willpower, and a lightbulb went off for me. No wonder I think I’m brave! I have willpower up the wazoo!  And I’m very, very good at getting myself to do the things I’ve decided I want or need to do.

What does this photo have to do with being brave, Amy? I have no idea, but I like it, so there you go.

What does this photo have to do with being brave, Amy? I have no idea, but I like it, so there you go.

Anyway, lately I’ve been having some trouble being brave, which is unusual for me, but, well, it’s happening. I’m having to use all my willpower, which I hardly ever do, and I’m still really struggling. Like tonight, I have to do this thing–have a conversation, actually–and thinking about it makes me feel literally ill, that’s how afraid I am to do it. But this is a great chance to notice some concrete ways to cultivate bravery, right? Right.

For instance, I know I want to avoid this conversation. It would be so easy to just…not do it. So I’ve made concrete plans around it to make it easier to do it than to not do it. And I’m writing about it here, and by the time this post publishes tomorrow morning, I’d better have done it. So I have created some built-in accountability. Yes, I could cancel the plans and I could change this post, but the effort of having to do those things will encourage me to stick to the original plan.

I’m trying to stay in touch with reality. Because reality is, this conversation does not have the power to destroy my life. Not even close. So thinking about unrelated stuff in my life that I’m happy about is actually really helpful for staying grounded and keeping perspective. Likewise, I’m doing my best to think about the conversation going well and all the reasons it might go well, and to avoid thinking too hard about the conversation going poorly. Aka I’m practicing positivity.

I’m doing my best to keep it simple. I find it’s really important when making plans to set goals I can actually meet. I don’t mean that you have to set easy goals, but rather realistic goals. Writing a novel, for example, is not easy, but I can make a plan to write a novel that, based on past experience, I’m pretty confident I can follow. So for this conversation, my goals are to show up and ask for one thing. It’s not going to be easy to ask for the one thing, and it doesn’t help that I hate asking for anything, but I’m pretty sure I can do it because at least it’s only one.

I’m being kind with myself. I’m using up so much willpower right now, that means I don’t have a lot of it left over for other things. Which means I’m not being super productive right now. But I’m being passably productive, and everything important is being taken care of, and that’s good enough.

And finally, I’m quite happy to lean on some good old-fashioned stubbornness, of which I always have a large supply.

I still think I’m a brave person. I think I will go, and I will feel queasy, and I will stammer a whole bunch, and I will have this conversation.

Just because bravery isn’t always easy or flashy or elegant or clean doesn’t make it any less true.

Sometimes I marvel at how much I don’t know.

You think as you get older, you’ll learn more stuff, and you’ll have more experience, and you’ll meet more people, and you’ll just know more. And that sounds pretty all right, as these things go.

But sometimes it feels like the older I get, the more I don’t know. Like, you’d think I’d understand other people’s motivations better by now. I’ve spent my entire life studying other people’s motivations. But, you know, a lot of the time, I really don’t have a clue. Often I can barely remember even the basic truism that other people aren’t automatically like me. So then all I can do is sit back and try to take care of myself, because that’s at least one thing I’ve learned how to do, more or less.

Or sometimes I look at another person’s circumstances, and I can see things are suboptimal. The person is not happy. They aren’t getting what they want. And it’s so easy as an outsider to think, well, obviously this person should do xyz, and that would at least be an improvement. But really, that kind of thinking is often silly. Because who knows what they should do better than themselves? Maybe there are more circumstances I’m not aware of. Maybe they’re trying to do xyz, but there are complications and difficulties. They may be obviously not getting something they want, but maybe they’re getting something else they want, you know? And who is in a better position to figure that out than the person themselves? There are exceptions to this (of course, because one thing I’ve learned is how often there are exceptions), but so often the answer is: No one. No one is in a better position.

Photo Credit: haslo via Compfight cc

Photo Credit: haslo via Compfight cc

I don’t always know about things I know a lot about, either. Like novels. I read Robert Charles Wilson’s The Affinities a few months ago–it must have been back in July sometime–and I wouldn’t have thought that novel would have worked if someone simply explained it to me. It skips time all over the place, which kept irritating me while I read it, and a lot of stuff happened that didn’t seem all that relevant, and the characters were not all that compelling. I was skeptical about the whole thing, but when I finished it, it all seemed to hang together and work to explore an interesting idea. And now it’s been three months and I’m still thinking about it, while there are other books I was reading around that time that I definitely enjoyed more but am not thinking about at all. So by at least one measure, it was a very successful novel, even though fifty pages in, I was wondering at the wisdom of buying it in hardcover.

And I don’t always know what choices to make in my own life, either. My path is not always clear.

This all reminds me of this old nugget: The wiser you become, the less you realize you know.

What I didn’t realize is that I’d still wish for all the knowledge I don’t have.


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