The Awkwardness of Pseudo-Dates

There are no stupid questions.

But there are damn confusing ones. Questions that beget more questions, filling the listener with untold uncertainty. Something as simple as “Do you want to come to yoga with me this Thursday at 8?” can contain layer upon layer of potential hidden motives and trapdoors which, if you take so much as the tiniest misstep, you will plummet into, and you can bet your ass there will be spikes at the bottom.

You may think dating is the worst, but the true epitome of unpleasantness is almost dating. At least when you’re on a “date,” you can shoot for the stars. Go for that kiss, and when you find your lips landing firmly on the cheek of denial, rest easy knowing that at least you tried. You may not have even made it to the moon, but thanks to the heat shield of certainty, your reentry into the atmosphere of loneliness will be smooth and relatively flameless.

But what about those other times, when you end up doing something fun with a girl, just the two of you, but nothing is ever specified? Is this romantic? Are you just friends? Was that stop to pick up a bunch of heavy objects after dinner truly spur-of-the-moment, or was the whole thing just a set-up to get your burly arms along on her errand?

There’s just no telling! Sometimes you’re on a date and you start to believe in the idea of mutual attraction. But other times one person is into it and the other is totally oblivious, and despite every sign you throw at her, she manages to dodge the hint.

Is her adroitness due to her obliviousness, or is it a concerted effort to avoid leading you on? And is everyone as neurotic about this as I am?

There you are, staying up late in your dorm with the girl of your dreams, just talking, experiencing one another, and it seems like neither of you wants to go to bed. Every lull leads to extended looks, and you can tell the feel of the evening is about to shift, but then conversation picks up again, and throughout it all, you’re too chicken try to take things in a physical direction. You’re good friends, and you don’t want to ruin that with your bullheaded presumptuousness. You’d be crushed if you revealed yourself, only to find out you’d read it wrong from the start. Eventually night drags on to dawn, and the two of you head your separate ways, last lingering gazes held until one of you closes your door.

Of course she’s into you, you dolt! But it’s impossible to convince yourself, and the devastation of being wrong is unthinkable. So instead you’ll let that moment slip through your fingers, and you won’t be able to sleep because the doubt and regret will course through you like a poison, and for the rest of your life, you’ll regret not taking that leap.

At least, that’s how it is for me. To be fair, I haven’t lived a complete life yet. Maybe I’ll have wild, romantic experiences that will get me to stop thinking about that night on the cruise ship when I stayed up with that nurse with the southern accent and watched the sunrise, and somehow didn’t kiss her. Maybe I’ll stop thinking about the time that naked girl called me into the shower to help her adjust the heat, and I did exactly that, then left. Maybe, but I doubt it.

And sometimes you end up on the other side. Someone will come to your apartment with her friend to bake cupcakes, and the friend will mysteriously have to leave, and suddenly you’ll be alone with this person you have no interest in, but now she’s hitting on you, and now she’s opening wine, and now she’s leaning closer, and oh god.

It’s a part of me, this inability to interact with women, to know what they’re thinking and what to say to them. It’s plagued me even longer than my acne or asthma or my ever-embarrassing tail.

My dad did his best to train me in the art of interacting with the opposite sex, but I took to his lessons like particularly inept oil takes to water. I think all of my failures and awkwardness and imperceptions can be traced back to a single moment, one I’ve never been able to live down. My dad likes to tell potential mates of mine the story of how, one morning when he was dropping me off for elementary school, a couple of girls from my class greeted me. Being relatively normal human females, they said something friendly, like “Hi Russ!” But even this simple salutation skyrocketed my scared-and-confused meters off the charts, leaving me too dazed to respond at all. My dad seized the moment to give me some of his point-in-time instruction, which was a piti.

I was a Nickel, and by god, I was going to learn the subtleties of basic conversation. In order to introduce me to the concept of pleasantries, he posed a hypothetical scenario: “Suppose, for example, you noticed that a girl had on a nice pair of shoes. What could you say?”

Ever clever, I immediately came up with the perfect comment:


Nailed it!

My father was impressed. Maybe I could catch on after all. So he took the scenario one shoe-step further. “And suppose,” he continued, “you didn’t like the shoes she was wearing?”

This was tricky. I was thinking something negative, and yet, to meet social standards, I was required to say something positive. A puzzle! I gave the situation a lot of thought, imagining where each potential response might lead, before answering with:





Filed under Observations

71 responses to “The Awkwardness of Pseudo-Dates

  1. Also, how do you break up from almost-dating…and what do you call it afterwards? A mistake? A thing? Is that the best we can do, saying that you had a thing with someone??

    • And how do you inform the other person that it’s over? Do you simply ignore them? Stop texting? Tell them about the “great guy” you’ve started seeing? Or have the awkward “I think we should just be friends conversation”, only to be made more awkward when they tell you that’s all you were the whole time…

  2. Kate

    that ended rather abruptly – much like many almost-but-not-quite-but-possibly-grasping-at-straws-but-may-be-a-date, dates I should imagine.

  3. TBT

    I was just in a similar situation. I just wanted to be friends. Go figure!

  4. Ah, see, the fundamental rule is that men have no taste whatsoever. Hence they are not even qualified to like or dislike a girl’s attire. Ergo, the correct response would have been ‘Hi, I am Russ.’ In both cases.

  5. To be honest, I don’t know how to interact with men appropriately too.

  6. So, what’s wrong with saying that last line about the shoes? 😛

    Hehe, another great post. I’ve been really enjoying your blog. And I totally get you – to me, I think it’s all about “playing games.” I abhor this. I wish people would just be honest – men and women. Then, instead of playing games, the guy and girl can, ya know, maybe try to advance the relationship.

    Even if the girl isn’t interested in the guy, the boy now has an opportunity to try to win her over, instead of frustrating himself with the question of “does she like me?”

    • I’ve always tried to advance relationships BY playing games. Turns out most girls aren’t that into World of Warcraft and A Game of Thrones: The Board Game 2nd Edition. Who knew?


    A window in the blue sky I want to open,
    and shout to my angel, I can not sleep
    since I have met that magical evening
    in my heart is broken out a new spring.

    I can not forget your beautiful blue eyes and
    open and your smile with your soft hair.
    Wearing a short dress all full of beautiful flowers
    full of charm and redundant in light color.

    I can not find peace in my most intimate thoughts,
    my memory inevitably turns yesterday
    when you smile, you were together in silence
    and have produced in me, dear, sweet charm.

    Now I know what the word love,
    want, with passion, and never forget.
    Come, please love beside me again
    Kiss me and spread love among human people.

    Vittorio Banda
    Copyright 2010

    • This is much better than my love poem from the Valentine’s Day post. Though I notice you’ve avoided the word “squawk.” An interesting choice, as I attempt to include it in every poem I write.

  8. I’ve been to pseudo-dates for like a month.I felt like something good was coming out but going nowhere.ugh! Love this post!

  9. Reblogged this on unpragmatic and commented:
    Indeed a very confusing phenomenom

  10. sj

    Why is the tail tucked under your shirt?!

  11. I am delighted that you men have just as much confusion as we women do. Delighted indeed. Just remember… A man is biologically programmed to assume that all women want him. A woman is programmed to assume that men only want one thing.

  12. Ohhh dating. Lucky me, I’ve had the same bf for quite a few years now. It was easy for us being friends first, then liking each other more, and the transition to bf/gf wasn’t awkward. Like I said, I just got lucky there. 🙂
    I haven’t had to deal with experiences similar to yours, so yeah. Have fun with that!

  13. If you like someone, just say so.
    I’m 39 now and I used to be very timid about all of the above. Wondering does he or doesn’t he. In the end, I have wasted a lot(!) of time… wondering about, dreaming.. Now I just say so. If he doesn’t, oh well, at leas I know and can move on… even hurt for a while maybe and then realize that he wasn’t worth it in the first place 😀
    Life would be so much easier if we were more straight forward!

    • I prefer to dance around the issue, making sure I squander the time when she’s actually interested so that when I finally bring it up, the magic is gone. It hasn’t worked yet, but I think I’m due.

  14. Oops!!
    Can see where the struggle comes in.
    One thing you need to remember though – dating does not progressively get better as you age.
    It gets infinitely worse!!
    So take one and keep her!!

  15. Love is one of those things in life that never changes. Men could be (I certainly am) better off giving up on understanding women; she is way to beautifully complex for me to understand, trying to capture her in the limits of my male perception would be imprisonment… Instead I admire and wonder, love and enjoy the strangeness of the female…

  16. Haha, you’re not alone. I asked a guy to hand me the shampoo once. He didn’t even look at me. He didn’t even notice my hair was still dry when I got out.

  17. TyTy

    Goddammit Russ! Pretty spot on. You never do forget…

  18. Oh God… It feels so good to know guys do think a lot too!!!
    We (women) are so wrong thinking you are “simple” (sorry), and that you mean what you mean… And now it looks as if you also struggle!! Woohoo!! Life is great!!
    I used to regret things that I didn´t make them happen… Now I usually regret things I have done… So at least, I tell myself that I tried!!
    Loving your posts!!

  19. Aja

    Almost dating sounds really lame. I’m lucky I’ve been dating the same guy for 3 years. Although I don’t think girls experience pseudo dating too often. I could be wrong, though.

  20. Your answer on the ‘not so beautiful shoes’ is acceptable I think.=)

  21. chunter

    “Could you wear different shoes?” won’t work until you know the person a little better…

    I want to give some really great advice but the truth is, I’m glad all that is nearly behind me! (Of course, that too is never 100% guaranteed but I’m pretty confident 😉 ) So my suggestion is, look forward to the day you don’t have to awkwardly date and try your best to be the person you’d most like to be with in the first place. You never really know about these sorts of things.

  22. Reblogged this on MyDestiny2011 and commented:
    Been there ~tell me about it :). Thank you for this one. I like it.!

  23. I didn’t want to ask this girl out on a date, because I figured that was too forward and I didn’t want to scare her off. So we went on “pre-arranged hang-out sessions” instead. Try using that term!

    I married her eventually, if that’s any consolation!

  24. noorcrumb

    I generally like to hang out with guys more than chicks, and there have been a few times where guys think I’m rummaging for a date. I try to give every sign that I’m not interested in anything beyond a friendship. For example, absolutely no flirtation, I even dress shabby, or when I propose to hang out, it’s usually in public, or if at home or at theirs, I don’t stay too late.

    I think I’m doing all the right things, but some men just don’t read those signs, or rather the lack of ‘romantic’ signs. So my question is, how can I make it clear to a guy that I want to hang out as friends without outright saying “Hey dude, I don’t want to have sex with you, I just want to watch some Curb Your Enthusiasm and play some video games.”?

    • I’m not sure guys notice things like dressing shabby. We’re too busy doing it ourselves. I think you’re just screwed (and not in the way the guys want), as evidenced by this video:

      • noorcrumb

        HAHAHAHAHA. Grrrrreaaaat….so I can pretty much assume every guy I’ve been friends with and are friends with want to bone me and are only my friend in the hopes that their wishes will one day come to fruition. 😦

  25. Funny stuff. And I always appreciate the hand-drawn humour.

    If we’re really honest with ourselves, everybody would admit that when two people are really into each other, it’s going to happen. No matter how much you insult a person’s shoe choice 🙂 If you’re not ripping each other’s clothes off by dessert, proceed to option 2.

    Difficult dates are the ones where you have to convince the opposite sex that they’re really into you. How you do that is up to you. Alcohol has a general success rate. Flexing muscles does not.

    • Sometimes I start ripping off a girl’s clothes, only to find that I’m doing it simply because her shoe choice disgusts me so much that I can no longer look at them. And I usually don’t get any farther than the shoes before she storms out.

      Perhaps alcohol will help with this issue as well…

  26. wildcrane

    I thought that purposely annoying a little girl is a little boy’s way to express fondness. Is there a cultural difference from early age?

  27. LOL! Maybe for now on you should write funny, quirky, love notes. 😉 LOL!

  28. Thanks for the laugh and for the reminder that being married has its perks!

  29. If I did not read wrong, I think your problem lies in the fact that you’ve been introducing your “potential mates of yours” to your dad, and him retelling of your unadeptness of complimenting the opposite sex. But man, I get you….
    Wicked post nonetheless… wish you have an unawkwardness in your future endeavurs.

  30. elisa

    OK, I’m waaaay past dating, but this still made me laugh out loud and remember painful moments. I especially love the look and fingertips on the “reentry into the atmosphere of loneliness” illustration.

  31. Dammit! 😀
    Yet again your post reads like you’ve scraped the inside of my painful youth (and current semi-youthish-thing…) because I have the same problem with women and its a joke because I’m good with words and language and people and can watch the world go by and fairly accurately assess so much and so many people, but when it comes to dealing with the other sex romantically they never cease to confound me…
    Why can’t women make it easier for us nice, simple guys instead of for the muscle-y hot guys who have an easy in by default!? I would think its the not-so-hot dudes who are “great on the inside” (I want to meet the women who are NOT 40 and actually practice that besides preaching it) who need a bit of an advantage or head-start or something, don’t you?

  32. Pingback: Friend Date Horror Stories « Sustained Enthusiasm

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