The Worst Internet Dates Ever

Although the idea of online dating was once sort of ‘frowned upon’ as the province of only the desperate or the strange, it is now more widely acknowledged that more people likely to be reading this article have at some point created an online dating profile or been on an ‘internet date’ than have not. Now, couples commonly meet online, where the exchange of personal information is more whimsical and less socially-governed than in other contexts such as the workplace or a bar where everyone is drunk and the meeting can only culminate in ‘sleeping together too early and then not having enough information about the other person to be sufficiently motivated to navigate the sea of ensuing discomfort to ever get to know each other’.

Thus the problem with meeting someone online is not, actually, the incorrectly-reported ‘shame’ [although a twinge of embarrassment at saying out loud to yourself, in the mirror, ‘I am on OKCupid’, is normal] , nor is it the fact that ‘everyone’ on an internet dating site besides you is liable to be weird/desperate.

The primary issue is that it is impossible, even for the most ruthlessly honest and skillful online communicators, to represent themselves online in a way that will accurately reflect the way they actually appear in person. The ‘connection’ that occurs while browsing someone’s pictures or while exchanging messages and/or emails can never, no matter how casually or comfortable it is executed, translate into a real world meeting.

Please peruse the following worst-case examples to assemble your own personal cautionary tale regarding attempting to meet people on the internet. You will note that both examples involve an individual who already had a boyfriend when posting an advertisement seeking an internet date. This is intentional.

Attempt #1: You are 23 years old. You still have a boyfriend with whom you are cohabitating, miserably. You are enduring the essential existential crisis which all long-term relationships eventually endure, wherein you find yourself thinking something to the effect of ‘this person seems to work well for me and perhaps my unhappiness is my own fault and if I spend a little bit of time leaving the house with other men I might gain some kind of like perspective.’

You post some kind of vague ad on Craigslist in which you are honest about your situation, explaining that you are in a committed long-term relationship and not seeking another romantic relationship, like, not exactly, except maybe you want to ‘see how things go’ or maybe just ‘make a friend of the opposite sex’ ideally who is also in a relationship so that you can discuss ‘relationship things’.

Your requirements for discovering commonality with someone else includes a list of bands. Your boyfriend isn’t into bands and you are and it causes tension. You express a desire to meet someone a little bit older than you, citing the desire to benefit from further ‘life experience’. You hear from someone who is 35, in a committed long-term relationship, seems friendly/interested in making new friends. You are too young to understand that healthy 35 year-olds are not likely to seek friendship with 22 year olds via Craigslist. He likes some of the same bands you do and a couple that are ‘red flags’ [commercial metal] but he writes well so you figure it’s okay to meet for a sushi dinner.

The sushi dinner is more expensive than you expected. He is short and overweight and pays for everything. You go drinking afterward. You get a stomach ache. After he has had several drinks he talks about how he’s unhappy with his girlfriend. He talks about ‘polyamory’. When you casually joke that you are so poor that you were considering selling your worn socks to foot fetishists on eBay, he gives you five $20 bills right before you say goodbye. His hands are shaking. You feel like a con artist or like you did something wrong. You email him later to thank him for the dinner and the money because he said you were going to be friends and maybe you and your boyfriend could hang out with him and his girlfriend. He never answers. You don’t tell your boyfriend.

Attempt #2: You are 24 years old. You have noticed your boyfriend never takes you on dates any more and you are experiencing a self-righteous sense of entitlement, so you create a profile on some online dating site, you forget which. You use cute pictures your boyfriend took of you when you were 22. This time you don’t say you have a boyfriend. You write about how you’re socially fulfilled [untrue] but intellectually lonesome [true], suggesting that the reason you don’t get out much is that you are too busy with your ‘career’ [you are a blogger] and that you would like a gentleman to take you out a couple nights a week.

You meet a heart surgeon who begins emailing with you. He writes beautifully. You both write beautifully. You feel that maybe your dull relationship is not ‘all there is’ for you, that there are probably other people out there that can write beautifully with you. You write multiple emails with just the right amount of flirtation. You have, like, everything in common. When you decide to meet he suggests a really nice place. You make up an excuse for why you’re getting dressed up and you go out.

The man you meet on the curb is your height. His teeth, which were not depicted in any of the images of himself he sent you, are strewn donkey-like from one lobe of his ear to another, and he is so happy to see you that he is laughing, a wheezing laugh that is pitched much too high. It’s like a guffaw. He won’t stop talking about how amazing it is to finally meet, while staring at you with serial killer eyes, breathing heavily. He brought roses, like, the nicest roses you have ever seen, pale yellow with bloodstained tips.

At dinner he buys like everything. You’ve lost your appetite so he buys more cocktails. They’re fifteen dollar cocktails. It’s dark in there. He talks about being a heart surgeon. You’re a 24 year-old blogger with a boyfriend, so you mostly ask him questions about himself. You smile really hard. Then he starts bragging about his money. He has an affected posture, like he is a petit actor playing the role of a high-roller. Everything you say is so funny that it causes him to lean in, stare at you with those pinprick eyes, his jaw hanging like a corpse’s noose, laughing that braying laugh. Even when you didn’t say anything funny, like, even when you just said ‘why is it so dark in here’. The roses he brought sit stiffly beside you like a tormentor’s flail.

You endure it as long as you can. You suffer being kissed on the curb outside the restaurant mostly because you feel bad he’s giving you cab money. He is a terrible, terrible kisser, a fat, slick marine purse of piano keys mashed against your mouth. You feel shaken and angry and violated even though you know this is all your fault. Return home wanting nothing more than to kiss your boyfriend. Leave the roses in the cab and feel too guilty to even touch him when you get in. Cry yourself to sleep until you realize it’s because you’re so, so disappointed. And guilty. You feel sorry for the doctor. You feel sorry for your boyfriend. There’s probably something irreparably wrong with you and you never would have known it if you hadn’t gone on the stupid fucking date.

Despite the fact you kept your consternation and disinterest quite firmly to yourself, the doctor doesn’t try to contact you again. Feel a mostly-numb stirring of deflation coupled with vast relief. TC mark

image – iStockPhoto


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  • John Morrow

    This is one of the best and most honest articles – not about internet dating – but about what it's like to be a twenty-something unsure of how or why one is still in a particular relationship.

    Awesome job.

    • Leigh Alexander

      thanks, i experienced a wave of self-disgust while writing it


    I'm the heart surgeon. I was just lonely. Don't misrepresent yourself online.

    • Evan Hatch

      you should take me out bro. heard good things about you.

    • pt

      Why do you do this on every article?

  • RahRah Underhill

    Interesting. Were these autobiographical at all? :P

    My girlfriend and I met online two and a half years ago. Actually, we were at the same concert, separately. We didn't even meet at this concert or anything. Day after concert she joins the musician's online forums, and so begins our relationship. But we tell people we met at the concert. It's like our little “secret.”

    We didn't meet off-line until she came to visit me three months after this concert. We live together now, but at the time I was 1300 miles away. The biggest issue for me at that point, that first meeting, was I noticed that she was an inch taller than I was. Maybe even just half an inch. But she didn't notice. So I tip-toed. Like, as much as possible. Even for the first year of living together, I tip-toed whenever we brushed our teeth in front of the mirror.

    One morning, I was still so sleepy while we were brushing that I forgot to tip-toe. She turns and looks at me, and says, “Wait… did you shrink, or did I grow over night?!”

  • Stace

    may i ask, did 'you' finally decide to either stay or leave the boyfriend?

    • Leigh Alexander

      leave. regret it.

  • Brian McElmurry

    Brave article! Your comment, in response to John Morrow, restored my reader's sympathy after feeling sypmathy for the boyfriend. This seems similar in feel to Lorrie Moore's “How to Leave”, or is just called “How.” I enjoyed it.

  • jmbg
  • Charles

    Not many writers can write something as honest as this without seeming self-indulgent/whiny/another negative connotation but I really like this.

  • dementia inc.

    I'm the 35 year old.How about a foursome?

  • GregJG

    This made me feel a bit strange inside. I'm a 36 year old male and I've never done the online scene. Just two weird for me plus stories from friends and I think I was right. Loved the article.

  • Matthew Glidden

    “The primary issue is that it is impossible, even for the most ruthlessly honest and skillful online communicators, to represent themselves online in a way that will accurately reflect the way they actually appear in person.”

    My favorite sentence of your article. Short of The Shadow, who can truly know another's situation? So much of Internet interaction is like clothes shopping–a long search for something that makes you look better than you did before.

  • El puto

    “The primary issue is that it is impossible, even for the most ruthlessly honest and skillful online communicators, to represent themselves online in a way that will accurately reflect the way they actually appear in person.”

    I am extremely interested in the possibilities of the internet and technology satisfying [almost communistic?] the basic human sociological needs. Perhaps one day, we will be more concerned with the converse of your statement. As for now, because of the subjectivity of human nature in general, it's impossible to completely describe yourself online – from your natural body fragrance, to posture and mannerisms – without some form of 'The Truman Show' going on in your life. When portraying myself on a dating site, I make my shortcomings known first and foremost – be it physical, intellectual, etc. – before portraying the perfect, omnipotent image of myself that is reality (jokes :). But yeah – nothing comes even remotely close to that raw sense of realism one feels when the initial communication barriers are completely removed.

  • Julian Tully Alexander

    I really like the reasoning behind going on the internet dates more so than the dates themselves.

  • Ashke

    I'm not sure this was really “the worst Internet dates ever” but it was a pretty good look at why Internet dating is not a good replacement for couples therapy and/or breaking up.

  • # SisterWolf

    This is a masterpiece. Obviously.

  • DoNotBecomeStavroguine

    Please. Leave the self-pity at home and get your own life in order. Being happy is not that hard, even though it doesn't share the aesthetic appeal of being publicly miserable. Instead of bemoaning your choices, take responsibility for your actions, for they are yours and yours only.

  • Paul Potter

    Thanks, Leigh. This would make an excellent short film. Done any screenwriting?

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