The Ups and Downs (and Downs and Downs) of Online Dating Apps: Notes & Tips from the Battlefield

When I first asked my ex for a divorce about three years ago, I knew it would inevitably mean a return to the world of dating. I dreaded that moment, and for good reason. Dating is an institution that is itself antithetical to my personality. It's all about superficiality, the quick sell, and even quicker judgments. And yet I tried it, off and on for two grueling years. At the end of all that, I find myself as single as when I started, though with two very close friends whom I initially met on dates. So all in all, I suppose I shouldn't complain. (Yet complain I shall!)

So why write about it now? I am hoping to help you, dear single reader. If you can benefit from any of my experiences, tips, and observations, then perhaps my journey will have been more worthwhile. So here are my thoughts.

The main app I used was OKCupid. It suited my personality best for two reasons: it has no character limit on profiles (and I am nothing if not verbose) and it uses compatibility questions to help you narrow down your choices. It should be noted, however, that there is far more art (and arguably just entertainment) about this matching process than there is science about it. (Google Adam Conover's excellent take-down of the 'science' of dating apps.) Still, scientifically valid or not, it is useful to be able to see that Jane X is a voter who likes Game of Thrones and hates Donald Trump as much as you do. It's far more useful than simply seeing a picture of her elaborate tattoos or her golden retriever Sam.

Unfortunately, OKCupid is a very buggy app. It never works quite as you expect it will, and I would, for example,  often log on to find I had a whole new list of people I had supposedly 'liked' (despite them all being people I most certainly had not even viewed). Their support is awful. And occasionally you get the feeling that any connections you make are pure luck, given that sometimes I would come across profiles with the tag "She messaged you!" despite me never having gotten any messages from the person.

Of course, you have lots of other options. Tinder, Coffee Meets Bagel, Match, Bumble, Zoosk, etc. The list seems to stretch on forever. But the idea is always the same: you have less than one second to grab a person's attention and hope s/he swipes on you, and then you go into a hopper of prospects. If you both swipe on each other or one of you messages, you get to start the 'get to know you' process. After a while, that becomes so repetitive that, despite your best efforts, you start to feel that you are just writing spam emails, constantly repeating the backstory, the same questions, the same repartee. It's mind-numbing.

Anyway, back to my adventures on my primary tool: OKCupid. I answered interminable questions and wrote a profile that was frankly WAY too long. That was by design. I was hoping to weed out the vapid and the lazy by exasperating them with my War-and-Peace sized essay. But I also injected it with a lot of humor, to help the determined ones in their journey through the labyrinth of my Byzantine mind. My reasoning was that anyone who could possibly get through all that would at least be worthy of a dinner.

So how did I do? Well, in the grand scheme of things, perhaps I shouldn't complain. As I said, my two closest friends here in North Carolina are women I met on dates from OKCupid. They are both very dear friends, and that's pretty special. But as far as dates? Ugh. SO many misadventures and SO many evenings of yawns. A couple of highlights:

-The Cyrano de Bergerac episode. One day I got a long and eloquent message from a very intelligent and attractive woman. I was blown away. So articulate. So insightful. She seemed to know me intimately just from my profile. I was so impressed. And each subsequent message only confirmed my attraction to her. So we finally arranged for a date. And it was....awkward. She barely said a word. And when she did speak, I detected none of the charm, intellect, and perspicacity that I had enjoyed in our written exchanges. Finally I said, "You seem sort of nervous. Is everything OK?" She teared up and said, "I have a confession to make. I really enjoyed your profile and wanted to meet you, but I'm just not that good at expressing myself. So my friend wrote my profile and all my messages to you." Cyrano whispering from the bushes! Ah, well! And before you ask, yes, I did inquire (indirectly): her delightful friend was married.

-Living in Tribes! Normally I was always very careful about vetting people before agreeing to meet. I read their profiles carefully, exchanged quite a few messages, and more often than not even had a phone call. But one evening, I threw caution to the wind and agreed to meet up with a woman I had met on the app that same day. She asked me to suggest a place, so we agreed to meet at one of my favorite restaurants here in Charlotte, Basil Thai. I should have paid attention to the warning signs, the first of which was pretty glaring: when I told her the name of the restaurant, her response was, and I quote, "Huh. I've never had Asian food before." "Asian food"?!?!? Dear gods. But I plowed ahead regardless. So here we are, having a drink and looking over the menu. She then asks what I consider to be a somewhat odd initial question: "Do you know anything about your ethnic heritage?" I responded that yes, as a matter of fact, I had done a lot of genealogical research over the years and had had my full genome sequenced and interpreted, so I knew quite a bit about it. She asked where my "people" were from, and I said that my father's side was Ulster Irish and had arrived in the Colonies around 1700, and my mother's side was originally Welsh, but had been residing in London for at least a generation before coming to the Colonies in 1652. Her eyes sort of glazed over, and she then gave me a rather incredulous look. And then said this: "How could they have been living in London in 1652? I didn't even think there were cities back then. Wasn't everyone just sort of, ya know, living in tribes back then?" Yup, folks. Living in tribes. A generation after Shakespeare died. And 16 centuries after the founding of Roman Londinium, which itself was likely on the spot of even earlier settlements stretching back centuries into the pre-Roman era. And that, kids, is why we always VET, VET, VET.

So how can you avoid such misadventures? Well, as it happens, I do have some helpful tips. These apply to any sex and (presumably) any sexuality; but you can judge for yourself and, as with all unsolicited advice, ignore or accept it as you please.

Pictures. Your primary picture will be the main driver of which direction viewers swipe. My advice is to keep it simple. I have to say that personally, I loathe those ridiculous Snapchat filters and effects. If I wanted to date a bunny rabbit with a dog's nose, I would go to one of those Furries kink gatherings, people. And for the love of all that is holy, people, DO NOT make me play "Where's Waldo?" It's fine if subsequent pictures show you with your friends, but your primary picture should be you alone. (And for heaven's sake, make sure you either blur other people or get their consent. And definitely do NOT include unobscured pictures of your kids. That is both creepy and potentially even dangerous.) Also, everyone should consider smiling, or at least not scowling, in their primary picture. When I see an angry-looking profile picture, I just think, "Unhappy, angry person I don't want to meet." And last but not least, do NOT show pictures of you and your ex (or even someone who could be mistaken for him or her). Talk about creepy. That is just bizarre. One woman even used her wedding picture, complete with the original groom! Yet another did the same but cut out his face, which frankly made her seem like a serial killer starting a cork board display of her next victims.

Profiles. The single best piece of advice I can give here is to avoid overwhelming negativity. I often read profiles that listed nothing but what the writer did NOT want. No smokers, no drinkers, no drug users, no separated men, no this, no that, no the other. When people ask you your hobbies, do you say, "Uh, not bowling, not skating, and not surfing."? Of course not. Focus more on what you DO what, not what you DON'T want. It's fine to throw in a couple of deal-breakers (e.g. my warning to Trump supporters and non-voters that they should just keep moving); just don't let the negativity take over the whole tone of your profile. It's a big turn-off. I also recommend avoiding the same hackneyed clichés everyone else uses. They get so dreadfully tiresome. Examples: "Looking for my partner in crime!" (IMMEDIATE left-swipe!) "No games!" "No drama!" (Nothing shouts you're a drama queen quite so loudly as you insisting you aren't into drama, by the way. When I read "no drama," what I hear is, "because I am such a fucking drama queen myself that I will provide more than enough for us both.") Finally, be HONEST. Look, there is no point in lying about your age or your height or your education. Because it will all come out in the end, and no good will come of your lie, I promise. Take the very tall woman I went on two dates with. She was exactly my height (6'2"/188cm). She expressed HUGE relief when we met and I turned out to be my stated height. Apparently, pretty much every guy she had been out with had lied about his height. She'd go out with a guy who claimed to be 6'3", only to find herself being stared in the throat upon meeting. And of course this meant she was immediately turned off, not by the height but by the lie. And the worst part was, she'd have been happy to go out with a shorter man; just not a short liar. So, uh, in "short," be positive, talk more about what you want v don't want, be original, and be HONEST, folks.

Messaging. Welcome to the tedious and repetitive world of dating app messaging! You've survived the Deep Dark Forest of endless pictures, you've braved the perils of the Morass of Despair known as the Swamp of Profiles. You have at last come to what seems like the end of your quest: you are actually communicating with another human being. Well, guess what? Your peril has only just begun. Because messaging itself is a minefield. You don't want to come on too strongly, but of course you don't want to seem too aloof. You want to seem interesting and perhaps show your quirks, but not TOO many of your quirks just yet, because after all, your crazy is something best drip-fed to people in the beginning, right? I usually preferred to keep initial communications simple, direct, and specific. By specific, I mean that the reader should feel that this isn't something you just copy/pasted from your last ten outreaches. I usually commented or asked about some particular thing that stood out in the person's profile. And let's be honest: nobody minds a bit of flattery. So now you're chatting. You're almost home-free. My best advice for this home stretch is: be yourself and keep the chatting phase brief. Too many connections fizzle out because they simply go on too long. Humans are social creatures, and while I am as big a fan of the written word as anyone, nothing can replace meeting face to face. So the best thing you can do is chat long enough to feel confident, and then just rip the bandaid off.

(I have to pause here and interject something serious that is specific to gender. It's easy for me as a man to say, "just rip off the bandaid and dive in!!" But as Margaret Atwood chillingly and all-too-truthfully put it, "[Men] are afraid women will laugh at them; [women] are afraid of being killed." So obviously take my advice with a grain of salt and only proceed when you're truly comfortable. Please stay safe out there!)

Well, I could go on for hours with more examples and more tips, but hopefully this little tidbit helps. Best of luck, folks! May you have better luck than I did!