Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

There’s a Fine Line Between Smart and Ass

Theres a Fine Line Between Smart and Ass guest posts  donkey 150x150Today’s guest post is written by Dennis Hong.

As anyone who’s ever suffered through a bout of online dating knows, when you’re filling out your dating profile, you have to type in these little packets of personal information.

One self-description that I invariably put down is that I can be a bit of a smart-ass. I put this down because… well, I’ve been known to make girls cry on the first date. You know how “curvy” has become the online dating euphemism for “grotesquely overweight”? Well, “smart-ass” is my personal euphemism for “may make you cry.”

I feel it’s only fair that I warn my potential dates in advance.

Not too surprisingly, I often get matched up with other self-professed smart-asses. Unfortunately, some people don’t seem to understand the difference between being a smart-ass and being an ass. Hey, I admit it. I’ve had issues with it myself. (Again, I made a girl CRY. On a FIRST DATE.) And, to be perfectly honest, I still lapse occasionally… er, frequently from smart-ass to plain ass.

You see, there’s a fine line between sarcastic and insulting. Being sarcastic takes intelligence, a quick wit, and some amount of lucky timing. Being insulting is just the clueless person’s substitute for true sarcasm.

Let me tell you about an evening once spent between two self-professed smart-asses who were matched up online:

We’re hanging out in my room. She happens to have a bottle of Diet Coke with her. She opens the bottle, takes a sip, then drops it and spills a decent amount of soda on my bed. I groan and say, “Alright, whatever. Here, get up. I’m gonna change the sheets.”

She says: “Don’t worry, we’ll just cover it up. You can change them in the morning.”

I say: “Ummm, I’d rather just change them right now. I’m not gonna sleep on a Coke stain.”

[SSSSSKRRRRRRTTTTTTZZZZZZZZZZZZ] Time out.

Theres a Fine Line Between Smart and Ass guest posts  transIf this article were an episode of some cleverly hip ‘90s sitcom, the action would suddenly freeze, and you’d hear the sound of a record scratching, followed by my snarky voice-over.

Or, even cleverer, I break character, look straight into the camera, and address the viewers, while everything around me—including my date—remains frozen.

And I say something along the lines of:

“At this point, ladies and gentleman, my date has several possible responses. Which do you consider to be appropriately smart-ass? Which do you consider to be walking that fine line, but still somewhat clever? And which do you consider to be just plain insulting?”

Animated text zips across the screen, and you see the following three choices:

[Swoosh] A. “What, is the caffeine gonna keep you awake?”

[Swoosh] B. “Oh, you’re not used to sleeping on a wet spot?”

[Swoosh] C. “What are you, OCD?”

“Now, ladies and gentlemen, which option do you suppose my ever-so-sarcastic date chose?”

Really, is there anything clever or ironic about that last comment? (Because, in case my ass is too smart for you to figure out, that’s what she said.) Or is it just… well, rude? What if I really did suffer from obsessive-compulsive disorder? What then?

As it is, I am somewhat anal, so I’m used to the OCD comments. If I was bothered at all, it was mostly because she’d warned me that she was extremely sarcastic, but all she’d done up to this point was pepper our conversations with comments like these, none of which I found to be particularly witty or clever. Still, it wasn’t that big a deal, so I let it go.

It only became a big deal when she decided to reference my supposed OCD-ness at least seven times over the next hour. Really? She couldn’t come up with anything new to say?

That’s where she crossed the line from “smart” to “ass.”

Okay, so where exactly is that line then? Do we automatically click over from funny to annoying between the sixth and seventh times we make the same comment? Is there some rule that will draw the definitive distinction between sarcasm and insult?

I don’t think so. I think we have to be take it on a case-by-case basis… like the Supreme Court’s assessment of pornography: “I’ll know it when I see it.”

That’s how it works with sarcasm, too: “I’ll know it when I hear it.” And in this case, she was definitely being insulting, especially when she kept bringing it up over and over and over again.

Of course, the worst part of all this is that I now have a permanent brown stain on my mattress….

Pop quiz: what’s an appropriate smart-ass response to this?

A. Whoa, I think you’ve got way more than just a bed-wetting problem.

B.  Suck it up. It’s just a stain.

See? I told you there’s a fine line between smart and ass.

Oh, and it’s not the hyphen. Smart-ass.

Check out Dennis’s new group dating advice site, LemonVibe, where everyone has to prove–not just announce–how smart their ass really is.


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5 to “There’s a Fine Line Between Smart and Ass”


  1. Abcde says:

    Oh JOY! This post came at the exact right moment in my life. Just what I needed! Ha thanks :D

  2. Peter Yogi says:

    Heyy!!! I just began reading your blog today and I love it! I love your style of writing. Checkout my blog. I don’t write that much but I try to talk about my feelings.

  3. AJ says:

    This was quite an interesting post! Indeed it’s real easy to create the perception you want on online profiles.
    AJ recently posted..Would You Like To Learn How To Flirt With Guys & Become More Attractive? Read on . . .My Profile

  4. I think that is so funny. I agree with you though that there is a fine line between being sarcastic and being an ass. Some people just don’t know when to stop, which becomes annoying, but to them, it may be funny.

  5. Daria says:

    This a such a good post. I just read a book
    http://www.amazon.com/How-Get-Boyfriend-Critical-ebook/dp/B009RZ8ZLU/ref=sr_1_1?ie=UTF8&qid=1350656496&sr=8-1&keywords=how+to+get+a+boyfriend%3A+7+critical
    by Mark Marino. It outlined some of the things women should do when they first meet a guy so that it doesn’t turn into a disaster. Hopefully he’ll write one for men too!