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I’m not over it.

Or so that’s what Jackie claimed. We were walking home from the bar earlier this spring and she brought up the subject more or less out of the blue. I suppose I’d have preferred she at least pretend to ask if I was or was not over The Ex. But she didn’t. She stated a conclusion – she wasn’t looking to test a hypothesis.

Our footfalls were like ellipses dot dot dot-ing through a brief, charged silence. Although she hadn’t posed a question, what she said demanded a response. To deflect her accusation I’d need to carefully choose my words. A blanket denial wouldn’t be credible, while freely spilling my broken heart’s contents all over the pavement wasn’t going to help me win her affection.

I’d been here with other women before. These discussions never go well. The women I’ve dated tend to consider signs of grief over a past relationship as one of the most richly crimson-hued of red flags. By the time Jackie brought it up, I’d already learned my lesson many times over that I ought to avoid the subject of The Ex at all costs, at all times. Everyone knows it’s a bad idea to speak of exes with bitterness or resentment, but I’d already discovered the hard way that you shouldn’t display even a hint of any residual emotional attachment – not a whit of wistfulness.

It’s a strange fiction to maintain.

After taking a pause to measure my reply to Jackie, I sputtered out something along the lines of: “sure, you’re probably right that I still feel sad about [The Ex], but my heart is open to finding someone new, and it’s been a long time, and if I’m still sad about [The Ex] it’s mostly because I haven’t been able to establish anything deep and lasting with anyone else since,” blah, blah, etc. It didn’t persuade her. It never persuades anyone.

Someone to come home to

Like all online dating sites, OkCupid claims they’ve figured out how to create order out of chaos and match its users up with compatible prospects. Their primary mechanism is to prompt their users to answer lots of questions. Some are inconsequential: “Would you buy your partner perfume or cologne as a gift?” “If your own toothbrush was not available, would you feel comfortable using a partner’s toothbrush?” Some are political: “Is it logically inconsistent to support the death penalty but oppose abortion?” “Do you think the government has the right to regulate the ownership and use of weapons?” Still others are aggressively invasive: “Suppose you’re dating someone who seems to have long-term potential. You discover that they want to urinate on you during sex. Would you consider staying with this person?”

Log on to my profile to see how I answered that one, folks!

OkCupid uses your answers to calculate compatibility, but everyone can also view each other’s answers. You know, so you can figure out whether the dude who posted four mirror selfies of his abs considers himself a radical feminist, a liberal feminist, an “other” feminist, or none of the above.

Here’s the particular question I wanna talk about: “Which of these options most closely describes what you’re looking for in your next relationship?” The answers you can choose are “someone to come home to,” “someone to go out with,” and “someone for tonight.”

The site promises you better matches if you answer more questions, and while that claim strikes me as pretty dubious now, I took their word on it when I joined at the end of 2012. I answered 200-300 of OkCupid’s questions in my first few weeks on the site.

And so in that first flush of excitement when I began online dating and it was working and attractive, intelligent women were, to my surprise, responding to my advances, I came across the question and I clicked “someone to come home to” without hesitation.

Since then I’ve looked at countless profiles and I’ve found that no one else, and I mean nobody, answers “someone to come home to.”

But of course it’s not like she wasn’t on to something

A week before I knew Jackie existed, and 11 days before we went on a first date, I wrote an email:

from:     me <me@gmail.com>

to:          the ex <theex@gmail.com>

date:     Wed, Oct 1, 2014 at 4:17 AM

subject:

Hi,

I’m writing you because I’ve been thinking about you. Not in a strolling-merrily-along-under-a-blue-sky-in-the-cool-autumn-air-being-struck-with-the-thought-of-oh-how-is-this-person-doing-I-haven’t-given-her-a-thought-in-so-very-a-long-time kind of way, but rather in a more or less continual way for the last two years.

I’m know there’s definitely a chance that I in no way occupy the same kind of footprint in your consciousness that you occupy in mine – the risk I ran, I suppose, when I casually bandied about hurtful, vain threats of “eternal sunshining” someone who cared about me. But I trust that you’ll be kind enough to read this letter, even if it doesn’t resonate very much. I’m prepared for it not to; indeed, I have to expect that it won’t.

There’s several things I want to express. I have changed in many ways over the last two years – in ways both superficial and deeply essential. On the more superficial end of things, I acknowledge a lot of personal failures on my part – failures that would have been relatively simple for me to address had I had the necessary wisdom (or more pointedly, the generosity and other-directedness). There’s the obvious ridiculously basic stuff like not exploiting you as my personal maid, and not inflicting hours and hours of video gaming upon you.

I haven’t played a video game to speak of since we broke up. I’ve also learned that keeping a tidy house is its own virtue – it just feels better. And it’s trivially easy to not strew my filthy clothes everywhere, and to run the damn dishwasher myself.

But trust me when I say I believe/understand there was much more to it than that.

I cringe inside every time “Not Fair” by Lily Allen comes up on shuffle. I was a selfish, ungiving, and uncommunicative sexual partner. I also looked physically slovenly in many ways at the end of our relationship – another manifestation of how much I took you for granted in the most literal sense of foregoing all effort to respect, affirm, and provide for a partner’s needs because I didn’t feel any real drive or motivation to keep you respected, affirmed, and provided for.

To this day on command I can make my heart sink deeply in my chest – like, feel actual literal chest pain – when I remember back to me sitting out in a dark, TV-blue-lit living room while you would repeatedly ask me to come to bed throughout the night.

I don’t intend for these recitations to be a way of pointing at myself as if to say “ATTN: I’VE ADDRESSED ALL MY ISSUES! YOU CAN TAKE ME BACK NOW! PLEASE!” Really, I don’t. Beyond my shortcomings that drove you away, you have your own life path of discovery and desire you’re on and I can conceive and understand that perhaps you just felt you’d gotten everything out of your involvement with me that there was to get and that it was time to experience new people in life and for all I know you’ve never once looked back.

I just want you to know that I empathize with the position I put you in at the end of our relationship. My email earlier this summer was intended to be in the same vein – even though I recognize in retrospect that ending an email with “I am not angry with you” could come off as presumptuous (“Oh, gee, thanks, I’m glad you’ve made that magnanimous pronouncement, oh forgiving one”). I didn’t mean that previous email to be a gesture of kindness on my part either – I meant it to be like, hey, I’ve now been on the other end of rejecting someone who wants dearly to be with me and I can identify with the many ways in which that side of things can be goddamn hurtful as well.

Because I’ve been on that side – the side of the one who wants to end things – I get that after a certain point your heart can go out to someone for any sadness or anguish that they feel over you but that sometimes it really just won’t change anything. So let that be part of my preface here, and I apologize for the heart ache (if any) that what’s below will cause you.

I miss you.

I have, with great thought and deliberateness, oriented most aspects of my life toward moving on from, transcending, or getting over the wrenching transition is entailed in losing someone who was as much an integral and big part of my life as you were. I spend a great deal of psychic energy trying to philosophically recalibrate my dependence upon romantic fulfillment as a source of joy, trying to achieve a sense of equanimity toward the loss of you and the risk of loss of future partners and striking a proper balance between detachment and total alienation, and I try very very hard to think critically about the pleasures I pursue – sexual, sensual (food, intoxication), ego-driven aspirations and vanity. All of those are transient and ultimately not real and I haven’t transcended those desires, but I think a lot about my relationship to them and how to stay engaged in the world without losing my mind in wild, senseless pursuit of pleasure.

As you know, I have waded into the dating world with wild abandon, meeting women at a relentless, frantic pace. It hasn’t worked. I mean, it’s worked to meet women and to fill up time and to have mediocre, emotionally empty sex. But I have found no joy in it and I have never come close to establishing anything approaching the kind of true emotional intimacy I remember feeling like I had with you. I have gone out with so many different women that what at first seemed like a hasty conclusion is now looming over me: I might not find that emotional intimacy again. I certainly haven’t found anyone with your incredible intellectual vitality, either, and I’ve found very few that share your thoroughgoing, rigorous commitment to principles of equality and social justice. And to top it off I haven’t found many women that I’m attracted to like I am to you.

None of this stuff is your problem and I’m not writing it to evoke pity. But follow along with me for just a few more paragraphs, if you would..

You’re a black box to me, by my own design. Since our breakup I have not looked at your facebook profile, I haven’t looked at your twitter account, I haven’t so much as googled your name. Your number is not in my phone, though one of life’s ironic twists is that for all the time we dated I never had it memorized, and now I can’t unmemorize it or make myself unknow it. At first it was part of an immature attempt to so-called “eternal sunshine” you – but as the months and years have gone on it’s just been self-preservation because I know there’s a very substantial chance that spending time gazing upon your life from afar would still seriously hurt.

. . .

When you were driving me to the . . . airport on my brief final visit, I told you if, after spending time doing what you want to do with other people and living on your own, you reconsider and you miss me and you think to yourself maybe you’d like to reconnect – I told you you should let me know.

I haven’t reminded you of that for two years now because I’ve been scared the answer would still just be no, and I also don’t want to throw it in your face for fear of seeming like I’m a loser who hasn’t gotten over it and who is trying to make you feel guilty because I’m spiteful and vengeful.

I don’t know where you’re at but I figured you also don’t know where I’m at because we haven’t talked at all for a long time. My heart is still open to you because through my post-[The Ex] journey you still feel irreplaceable to me. I would like to think that these feelings would diminish over time, but they haven’t really diminished at all over two full years. I continue to think about you daily and suspect that I will for a long time. So consider this more or less an open ended invitation, if you weren’t still aware that one existed.

In the mean time I am going to continue striving to be a more humble, kind human being. I am trying to write a novel. I’m a real [job title] now . . . not a joke of a [job title] like I was when you were around. I am pursuing spiritual enlightenment – though who knows if I’ll ever find it or if it’s even a real thing to find.

I am trying really hard for my life to cease being marked – or even more strongly: defined by my losing you.

Take care, [The Ex]. I don’t really need to hope that your academic program is going well because you’ve always been a rock star and I more or less can presume that it’s going very well. I hope that you have found companionship, romantic/sexual fulfillment, and joy in your life down there. I hope [dog] is well too.

With malice toward none

I’m a pretty serious regular at my neighborhood coffee shop, and I’ve become buddies with one of the baristas there. He’s been dating someone for about a year and I’m not really acquainted with her, though I recognize her. One night a couple weeks ago he was closing and I saw her come in an hour before to hang out and await the end of his shift.

A mundane episode, I’ll admit. But I was moved, and then I was struck by how strange it was that I was so moved. As gestures of intimacy and devotion go, it was pretty minor. But set against the backdrop of the last few years during which connections slip like sand through my fingers, it was downright beautiful. And it felt (feels) acutely remote from my life right now.

The following are anecdotes regarding how my most long-lasting online dating relationships have ended. I’m not sharing them in the spirit of casting blame or settling scores or whatever. They’re not tales of injustice. And I’m not a victim. They’re just things that happened.

While breaking up with me, a woman cited as one of her reasons that I liked being “little spoon” too much. I am not making this up. She had other reasons too. But still.

I dated another woman who I always thought had beautiful eyes, and yeah, I liked looking at them. One night while lying in bed with each other, face to face, she told me “I feel like you’re trying to gaze into my soul.” She meant that was a bad thing, I guess. She broke things off a few days later.

The aforementioned Jackie and I settled quickly into a rhythm of seeing each other almost daily about two weeks after we met. A little bit after that, she asked me for advice on how to end things with the other guys she had met off OkCupid. A little bit after that, she told me she would be going home over the winter break and invited me to come visit her while she was away. A little bit after that, she preemptively brought up that she didn’t want to be exclusive and she didn’t want a relationship with anyone right now.

I didn’t go visit her over winter break.

I’m disappointed by all those endings.

I have reason to believe that each of those women drew back or pushed me away because they thought I wasn’t over it, but I’ll spare you the details.

I could tell you stories of how things ended with women I went on 3-10 dates with that’d make your head spin, but no one’s got time to hear ‘em all.

I’m not blameless and I know I’ve hurt people, too.

I could’ve grown to love a lot of individual women I met through online dating.

I want to think that.

Arguments

1. When a dog dies and its owner goes to pieces with sadness, no one would ever point to that grief as proof the owner couldn’t properly love and care for a new dog. And no one would tut-tut the owner for adopting Rex before she “got over” Fido.

2. The conventional rationale for being wary of someone who’s not “gotten over it” is the fear of what happens if the ex comes back. But no connection with anyone is perfectly secure. Everyone’s got exes orbiting them, whether they show signs of nostalgia for them or not. And there are billions of not-exes around who could lure your lover away at any time. No one’s ever truly “in the bag” and there’s no way to ensure they’ll never leave.

3. But seriously. Don’t worry – she’s not coming back.

Seeking new beginnings (still), notwithstanding

There are memories of events that definitely took place – you’re certain they happened – but those memories nevertheless become increasingly hard to trust as time goes on, just because they feel so thoroughly alien. Doubt creeps in.

One such memory of mine is of The Ex and I getting into cutesy, playful arguments over who loved the other more. I would say I loved her more, and she’d crinkle her nose and vehemently object and tap me on the face and say she loved me more, and we’d go round and round protesting to each other: nuh-uh, I love you more. This was a habitual dispute we’d get into.

When The Ex ended our relationship and I was faced with the prospect of starting over with someone else, I figured the task would be daunting, but I had a great deal of faith that a little self-improvement and a bit of earnest application would get me there reasonably quickly. I didn’t yet then appreciate how fortunate I had been to have had a multi-year, cohabitating, highly affectionate relationship with someone who was simultaneously a best friend and lover. I think I thought, at least subconsciously, that relationships like that came naturally (to the worthy, as I assumed I was) and were relatively easy to find.

Consider me now fairly disillusioned as to that particular belief.

But so what I’ve struggled with mightily is the question of why establishing something with a new partner comparable to what I had with The Ex has proven so elusive.

One thought I’ve kicked around recently is that there are lots and lots of people out there who have never experienced anything remotely like the relationship (I at least felt like) I had with The Ex.

For them, that kind of relationship doesn’t fit within any sort of template they’re familiar with. And so I’ve been dating in a state of mind where I am ready for, or even expecting, something stable and good and loving to develop, and quickly. For lots of people who’ve never had a comparable experience, something stable, good, and loving might feel weird, scary, smothering, or mundane.

No one on OkCupid answers “someone to come home to.”

With that in mind, is it possible that possessing the memory of having had something spectacular in the past is a great privilege, rather than a heavy burden? If it’s made me ready to spot what’s true and good and real when it’s on offer again from someone new, having such a memory could be an enormous asset out in a dating world where lots of folks are muddling through, totally ill-equipped to find superlative connection when it’s presented to them.

Such a realization might help me turn what’s felt like a loss without end into a steady foundation to build upon.

Here’s hoping.

To help the wayward learn how to send messages, or hell, just for the sake of sheer naked exhibitionism, I’ve posted every first message I’ve sent to women through OkCupid. There’s 221 in all, spread over the last 26 months.

Peruse them at your leisure here.

I’d never heard the term “DTR” before reading Maureen O’Connor’s article “How to Sneak In (Or Out) a Relationship’s Back Door” but I immediately recognized it as one of the core issues to confront when dating a bunch of people you’ve met off the internet (or through any other means).

Just like with discussions about STIs, in an ideal world we’d all sit down and have sober, earnest, forthright talks about our feelings regarding the course/path of a relationship and we could communicate our desires openly and fearlessly.

More realistically, moments where we try to “define the relationship” with someone who falls in the vast middle ground between fuck buddy and fiancée often are catalyzed by awkward social encounters (“So I noticed tonight you introduced me as your girlfriend, but…”), drunken desperation, or just irrepressible insecurity that you just can’t hold in anymore. And the protagonist in O’Connor’s article is more or less right that until you DTR, very few things are offlimits – though that doesn’t mean you won’t feel a bunch of guilt and confusion every time someone you’re dating (pre-DTR) texts to ask you what you’re up to and you hastily send a text that says “not that much, you?” during the brief interval between when your current bedmate walks off to take a postcoital bathroom pit stop and when he/she gets back.

A friend of mine asked me how things went the last time I had a DTR discussion and I’ve reproduced our discussion here:

Need help understanding all the online dating lingo? I’m here to help.

They say… But they actually mean…

• A guy’s profile filled with standoffish sarcasm —> “I have too much involvement with the pickup artist community.”
• “I don’t know why I’m on an online dating site.” —> “I look down on you for being on an online dating site while I am actively browsing online dating sites. I am large, I contain multitudes.”
• “I love to travel.” —> “I got really wasted studying abroad in Scotland and that was pretty awesome.”
• “I really love to travel.” —> “My family is rich.”
• “I love to be active” —> “You better not be fat.”
• “A healthy lifestyle is important to me” —> “You better not be fat.”
• “New York Times” —> “Behold my erudition.”
• A man’s picture where he’s looking away from the camera and not smiling —> “I’m okay looking like a tool, because the OkCupid data told me to.”
• “I am in graduate school” —> “I am paying for a master’s degree.”
• “I barely have time to read for fun anymore.” —> “I repeat – I am in graduate school.”
• “I am a 34 year-old man, seeking women age 24-35” —> “I want to date 22 year-olds.”
• “I hate writing about myself.” —> “I have learned to try to conceal my ego, but I haven’t yet figured out a subtle way to do it.”
• “I last read: the Hunger Games.” —> “I do not like books.”
• “I last read: Fifty Shades of Gray.” —> “I hate books.”
• “I last read: Tom Clancy.” —> “I hate women.”
• “Oxford Comma” —> “New York Times.”
• “I am a feminist” (said by a woman) —> “Despite pervasive popular ignorance about the meaning of feminism, (e.g., many men wrongfully thinking that feminism is radical, anti-man, emasculating, and therefore something to be avoided at all costs) I am standing up for what I believe and making it clear I expect to be treated decently and as a human being rather than as a mere female sexed body.”
• “I am a feminist” (said by a guy) —> “I know what these women want to hear.”
• “Yoga” —> “You better not be fat.”
• “I am a woman, seeking casual sex.” —> “This is a not a real account.”

So you wanna online date.

You just got dumped, or you’ve already dated all your decent looking friends’ friends, or whatever. Someone told you there’s a bunch of cool people on OkCupid or a bunch of successful people on Match.com or a bunch of people watching the minute hand on the biological clock rotate on and on on eHarmony. (Or so I imagine – never joined that one…)

If you’re looking for anything more than genitals getting creative with orifices (or vice versa), you’re gonna need to write yourself a profile and if you wanna meet someone interesting, it’s gonna have to be kinda good. And most people have no idea where to start.

Rule 1: Reflect, Reflect, Reflect

The point of a profile is to attract the kind of people you want to meet. Give this some thought! The number of people floating around on dating sites can be overwhelming and there will never be time to date them all – even if by some miracle they all wanted to date you. You might want someone who lives to work and climbs the corporate ladder with ease, you might want a political activist who wants to change the world, an artist or musician. Do you want a deep thinker who will match profundities with you all night at the coffee shop or a weightlessly hedonistic hardbody to dance with you downtown? Someone with a passport full of stamps or someone who can dress a carcass after a hunt?

You get the idea – and I’m getting sick of trying to pose examples of mutually exclusive personality types.

You don’t need to compile an entirely comprehensive list of all possible desirable traits in a mate – but you should think of some characteristics that would be high on your wishlist because the next order question is “what is the type of person I’m looking for looking for?”

Once you’ve psyched yourself out with all this self-reflection, you’re ready to start typing!

Rule 2: Don’t self-characterize

OkCupid and Match, and probably other sites, all ask you to summarize yourself. A lot of people take this too literally and write something like:

“Oh, I hate talking about myself! But my friend told me to join, so here goes: I am funny, sarcastic, quirky, open, honest, I am a hard worker, my friends would say I’m dependable. I’m a shoulder you can cry on, I love family, and I’m all around AWESOME!”

Yeah, alright.

There are a couple big problems with self-characterization like this. The first is that it’s off-putting – while online dating inherently requires a degree of self-promotion, when else would you feel comfortable asserting to strangers that you possess a bottomless supply of desirable personality traits? English 101 taught us “show, don’t tell” when writing creatively, and the same is true about profile construction. You should be able to demonstrate your sense of humor through your profile, or someone should be able to infer your commitment to earnest sincerity or personal growth from what you have to say, not just by saying it.

The other huge problem with self-characterization as a cornerstone of a profile is that it provides no common ground that someone cool could start from. Even if you’re hilarious and incredibly honest, a visitor to your profile can’t craft much of a message around that.

You can boil this down to the advice of talk about what you like instead of what you are. What’s a fun weekend to you? What do you want to accomplish in life? What values do you hold dear? Which brings us to…

Rule 3: Be specific

There’s a prompt on OkCupid that’s called “the six things I could never do without.”

Some make a pretty lame stab at being funny and answer literally (“1. water, 2. food, 3. air..”), but nearly everyone else answers with a near total lack of imagination. Countless people answer with “family,” or “the internet,” or “my iphone,” or “coffee.”

I guess if you want to cast a net wide, you’re not gonna alienate anyone by saying you like your family or coffee, but it’s not gonna help you connect with anyone that actually may share some real, deep-level compatibility with you.

You should take some risks in your profile and try and identify parts of you that are controversial – issues/values/choices/lifestyles that not everyone shares. If you have interests a lot of people profess, take it a step further. Everyone in the world (if online dating profiles are any guide) loves “travel,” but does travel mean taking an RV to Mount Rushmore, pub hopping in Dublin, taking ecstasy at a beach rave in Thailand, doing missionary work in Uganda, or what? (I have a near 100% response and subsequent date rate of return when messaging with women who have been to the same countries I’ve been to)

You gotta strike a balance, though, and make sure to remind yourself of the question “will this help someone identify/connect with me?”

For a good example of pointless specificity, look to the profile of any dude who holds forth on the finer points of his taste in beer:

“I like my IPAs hoppy, but I also tend toward the Belgians, but lately I’ve been enjoying the subtlety of a good pilsner.”

Lots of dudes seem to think this crap is important. Have a lot of successful marriages been based upon the cornerstone of shared opinions about beer? I doubt it.

Rule 4: Play to your strengths (sincerely)

After 10 months of online dating I’ve safely come to the conclusion that the most three valuable words in my profile are “I am feminist.” Woman after woman has either commented on that during the messaging process, or has later revealed that that was one of the big reasons they chose to meet me.

That said, I am feminist, and it’d be a pretty bad idea to strike that pose if you couldn’t back it up. Being acquainted with a number (more than one!) of people who are working on or have completed PhDs in feminist theory, I can string together a sentence or two if someone asks me what I mean. And I mean it!

A lot of people are bashful about hyping themselves up – but this is online dating and everyone knows you need to self-promote yourself a little bit. Do some bragging – if you have accomplishments it’s fine to share them. If you’ve cultivated refined interests/knowledge show that off too (within reason).

Think of what makes you distinctive and valuable – and make sure that comes out in your profile.

These ideas are a basic primer. Profile construction is a tricky hit-or-miss process. Hope these ideas have been helpful to you as you get started.