I Don’t Know How To Date

I don’t know how to date. This has come to my attention in recent weeks, months, or more specifically, the last 15 years or so. Every relationship I’ve ever had, I’ve just sort of fallen into where dating wasn’t really part of the equation. I always thought I was lucky in this regard, but I no longer feel that way.

To me, dating is the worst. I do not care for it at all. And to be honest, most first dates rarely end up in a second, because I’m wonky and my social skills are definitely a bit questionable. Getting through a date is more stressful for me than fun; in fact, I find I’m more relaxed when I go to the gynecologist.

Recently, I went out with a gentleman caller. He was a friend of a friend. I was forced into it as some sort of distraction for a recent falling out with an on-again, off-again love interest who ended up falling so below par that being with him became heartbreaking and disappointing.

I had tried to emotionally prepare myself for the date (read: had a martini and a Xanax before heading out the door), and had also cried out any possible tears that might pop out later in the evening, as I am a bit on the emotional side lately. I had also gone to the effort of putting on lipstick and even shaved my legs right before just in case things got hot and heavy. I’ll actually admit my reason for going on the date was more to hoping to get laid than find some lasting sort of relationship. This, I fear, is the boy in me.

The martini and Xanax were a bad idea, of course. Halfway through the dinner, I proceeded to tell my date that I didn’t know how to date, that I hated dating and that I didn’t care to go through the process of ever getting to know anyone because I already knew everyone I wanted to know except for Ryan Gosling. Furthermore he, my date, should know that I already met my soulmate, and although he was probably drunk in a gutter somewhere in Bushwick, as I spoke those words, someday, it was going to make sense and said soulmate and I were going to get our shit together and it was going to be perfect in a fantasy world with pink unicorns and bunnies named Fred. Yes, that’s what I told my date in a round about way. I have not heard from him since.

Of course this makes perfect sense, because had someone told me some malarkey about pink unicorns and bunnies named Fred, I, too, would avoid them like the plague, and I like those things.

So I went home and had a moment similar to the one Annette Bening had in American Beauty – the one where she cries and smacks herself to stop being such a baby. I didn’t smack myself with my hand, but rather with words. And in the moment I was forced to recall the so many first dates I’ve been on, and all the reasons they never resulted in a second. Granted, 70% of the time the choice to not have a second date was mine because I have obscenely unrealistic standards and again live in a fantasy world where everything is perfect. However, that 30% was not in my control. I had literally lost the chance for another chance for the same reason I had with my most recent suitor: I just don’t know how to date.

I don’t know how to make small talk and have it involve into topics more interesting. I don’t care to ask questions or even offer up any information about myself. I don’t try to be charming, because it seems like such a waste since I’ve convinced myself that there are only three people who have ever existed for me in the history of the world and two are dead – F. Scott Fitzgerald and Henry Miller – and the other is drunk in a gutter in Bushwick. I am absolutely completely closed off and by most accounts a curmudgeon. Women my age should not be this way so early in the game, but I am. This does not make me innovative or even a maverick; it makes me a narrow-minded asshole. Someone please tell me why there isn’t a class out there I could take to remedy this issue, or at least teach me how to be more relatable to the opposite sex so there is the slightest hope of eventually procreating with someone, anyone.

This weekend, I’m going to try this dating thing again. Once again, a friend is setting me up. I have already decided there will be no pre-gaming in my apartment, no mention of my soulmate – although he is, FYI – nor will I bring up anything about mythical animals or my disappointment in the whole dating process. No, instead I will do what they do in the movies and smile a lot. I will laugh at jokes that aren’t funny and put my wonky ways on hold for the evening if only to prove to myself that I can get to a second date and maybe even a third or fourth. Although to be honest, a don’t see a fifth one happening… by then I will have unleashed the real me and that takes a certain breed to be able to handle that level of madness, er, uniqueness.

Here’s hoping it’s just a “not enough practice” thing as opposed to a “missing the dating gene” thing, but I guess only time will tell.

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    • andrea dunlop

      My experience as a publicist has helped me out a ton with the early stages of dating. I work with writers, who are not the most naturally social bunch so it’s been a necessity to learn how to draw even shy people out and put them at ease. I’ve found that almost everyone has at least one area of expertise or interest that they can talk about for hours if they get an interested listener: so if all else fails, just dig around until you find that topic and let them run with it. This can put both parties at ease AND help you not pull a major over-share if that’s your wont. It’s also usually more interesting and telling to listen to someone talk about what they’re really passionate about than just make small talk.

      As far as actually opening up to another person, I can’t help you there as it’s common knowledge that publicists are dead inside

      • Mallory

        From one PR bro-ette to another, I love you, Andrea.

    • Kellie

      I forget where I read about this, but there actually is a college out there somewhere in the USA that offers a dating class. Maybe it’s like a psyche class where one of the assignments is to date, but there are certain rules, like no getting physical until the third date, blahblahblah. I have it bookmarked somewhere in my favorites because I, too, do not know how to date.

      Anyway, I feel you, man. You are not alone.

    • Chameleon69

      I just went through the same thing on Friday. Went on a date and tried to be open minded….I’ve become jaded in my old age.

      He showed up in nice jeans and Kenneth Cole shoes, but I couldn’t get past the open white button down with a ribbed black wifebeater underneath…and to top it all off, the accessory of a beaded necklace. You know the ones you get when you stop at some kiosk when you get off your cruise. Hoo Boy.

      We found out I worked with a relative of his a long time ago, so he sent him a text msg to say if he remembered me. His relative’s text response – “Yes, I know her. She’s easy! Have fun!”

      He walked me to my car and then proceeded to jam his tongue down my throat. Umm…hello? I’ve known you for three hours! You don’t get to do that. And I didn’t come in at any time to offer that. I prefer conversation chemistry on the first date, not a coldsore.

      He must have missed the part of the conversation where I said everyone I ever seriously dated I was friends with first.

      I’m just done with all of this!

      • Amanda Chatel

        Ugh… the beaded necklace would have had me out the door and running. It’s hard to be open minded when it comes to beaded necklaces and puka necklaces…

    • John

      Maybe its because you’re a shallow stuck up bitch that wouldn’t date someone, no matter how excellent they may be, because of the color of their socks. You have a lot of growing up to do, as it seems you still hold the maturity of a 13 year old.

    • Amanda Chatel

      @ John… you hit the nail on the head. I am those things. We all have our quirks and those are mine. But thanks for your feedback, white sock wearing guy!

      • Antome

        I despisse the “bitch” thing John said and not to mean you’re shallow, but what would you thing if you, say wear a purple shirt and one doesn’t like it and discards you? You would say he’s a shallow little weasel, maybe gay. I bet. But what if he can carry off the white socks with style, he’s aware he’s bucking the trend, he’s cut funny and stylish, and he care for the white to be pure white, showing he’s not slobby about details? You’d change your mind, unless you’re hopeless ;).

    • LasViega

      You, ms. Amanda Chatel, strike me as a stuck-up, sad, little girl. Yes, you must be definetely be younger than your age!

      I’ve read some of your articles now. Along with this one, of course. This one being just *whine & blah, blah, (etc)* IMHO. Maybe you have become too accustomed to self-pity and imagined misery? Well, you’ll get no sympathy from me… Zero.

      Some of your other articles are just incredibly narrow-minded/judgemental. Of course they also come with a “goodie-old” dose of *whine & blah, blah* and whatnot, including a load of hogwash. That pretty much sums it all up, no?

      So, you don’t know how to date? Ah, it could just as well be for the better, because quite frankly, any decently reasonable guy shouldn’t even waste five minutes of his time dating somebody like you…! I know I wouldn’t. Not if hell froze over, either. (Time wasted writing this answer doesn’t count).

      I’d rather go for a girl wearing sweatpants. And white socks.

      • LasViega

        Correction: *You must definitely be younger than your age.*

        By the way, good luck on getting the “dreaded” sweatpants and white socks banned.

        That’s all.

      • Antome

        As well as we may have critics about somthing about one, I have to make you reflect about the poison you blarted out. You are outright insulting her, as i think she’s not evil in any means or overall shallow as you said what if a girl said this about you? Only her relief about white socks is shallow, but most girls are much more harsh and broom assed about this matter.
        But i’d also prefer a girl in sweatpants and white socks over a shallow girl.

    • Jennie

      @LasViega HAHAHA. You can’t spell at all. You sad little man.

      It seems to be men who have issues with this article – that is clearly meant to be funny – than it is women. In secure much, guys? At least there’s always masturbation for ya.

      • LasViega


        That is “insecure”. As in one word. And “In secure much” is grammatically incorrect, as in fact non-existent. Hey, don’t be mad at me, you’re the one who brought up the subject in the first place!

        I corrected my misspell – the fact that you even brought that up…

        …that makes you one sad, little woman. Just like ms. Chatel. Not to mention the fact you seem to share her distorted point of views… I’m tempted to mention ‘pathetic’, too… Oops, looks like I just did. The world is a better place without people such as you and ms. Chatel – as a matter of fact I wish you would bury yourselves in a heap of dirt and remain under it. As far as I’m concerned, you’re both unwanted. Yes, you read correctly. No offense.

        Thankfully there *is* masturbation, yes. The choice between masturbation or women like ms. Chatel and yourself? I recommend ANY guy reading to go with masturbation. I just wish people like you never would have babies with anyone. Sadly, that is probably what people like yourself do. The result being more numbnuts with the same imbecile morale.

    • Jen

      Um…maybe you just need to get over your ex before you start dating. Why are you in such a rush to get into a relationship? I think you should start focusing on self-repair and happiness before you try to bandage the gaps you see in yourself with the companionship and assurance of another person. Someone told me once – “you want to stand next to someone, not lean on them. So get your shit straight before you start looking for another person.” No one’s going to ride out of the sunset to save you. Learning to date isn’t about learning to bat your eyelashes at another person. It’s about learning to be happy with yourself and finding someone else that’s happy with you too.

    • TJJ


      I can completely relate on all levels, other than the pink unicorns and bunnies named Fred.

      Despite my disdain for small talk and self-marketing, I too am venturing out onto the dating scene in hopes that I might find one (I’m only asking for one!) guy who I can genuinely relate to, and one day procreate with.

      I always imagined and hoped that I would fall in love with someone inadvertently, while busily working away on some joint project. I thought, perhaps, I had. I met a man who I enjoyed, respected and felt safe with, while canvasing for a political race. However, after almost three years of hoping and no signs of future marriage, I had to let the relationship go. Hence why I’m on the market…I could have sworn he was my soul mate.

      Some of us come at life from a different angle, you can call it the road less traveled or marching to the beat of a different drummer, but, however you choose to frame it, it means that not everyone is going to “get” us. We may have to go on a few more dates than the norm to find the one who does, but I believe they’re out there.

      Your gutter dweller is not the only one who will appreciate your soul. Trust me, cause I found your “uniqueness” funny and refreshing, and and I think that if I were I guy, I might just be interested in a fifth date.

      Good luck!

    • Brunettebambi

      Try reading “Act like a lady, Think like a man.” It WILL help if you really read it and do what Steve Harvey say to. Good luck to ya, you sound alot like me : )

    • typewritershoes

      Hi, ummm. I’m a male (read as someone with an outtie “below” the belt)

      I read the comments below after thoroughly enjoying this article and I must have missed something?

      Well, whatever it was and I guess somehow I should hate the article, the author as a person for some reason, basically all this and a bag of sourdough bagels “day old” not fresh because they’re cheaper that way,

      I really appreciated the article a lot.

      I found it because I typed into google search “I don’t know how to date” from my own just now (ongoing) dating frustration. Yes, obviously I’m wacko with words, as if I’m the only person on the planet.

      I especially appreciated that you were honest and at the end didn’t give some lame blow everything off advice that would be bullshit anyways. (of course it would be bullshit)

      You were just honest. Looks like it set some people off maybe?

      Honestly tends to do that sometimes.