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Online Dating For The Immensely Awkward

Updated on March 23, 2012

After years of stubborn avoidance and foolish pessimism, I plunged (more like jackknifed) into the extremely shallow waters of the online dating pool (we're talking like 5 inches deep). And as expected, the experience has left me a bloody, babbling mess of virtual skin and bone. Sounds depressing...yes, but there is an upside. I've got oodles upon oodles of material to share with you my fellow lovelorn reader.

How I actually got to this point is hard to explain, so I guess I have to flesh it out from the beginning. Warning: The following events may be slightly fictionalized for dramatic effect.

"Ok Cupid...your right, those Quiver matches are perfect for me. (gulp)"
"Ok Cupid...your right, those Quiver matches are perfect for me. (gulp)"

How It All Went Down.

It was New Year's Eve and like any man who questions their moral, social and economic standing, I made a resolution. I was determined to give serious dating and true romance another go. Yet, at the same time I wanted to efficiently sift through thousands of potential date options, all from the comfort of my sofa whilst eating Five Guys Cajun fries. So how do we go about dating of course.

Being both cheap and skeptical about this whole dating via computer thing I joined OkCupid (the place for bargain basement romance). I set up my profile, gave myself a username: notAScammer28, and filled out a series of silly self-assessment questions like:

What is the most private thing you are willing to admit?

I ain't sayin' nothin' seeee. You copas gotta bum wrap seeee. Me and old mickey were at annie's speakeasy all night see.

. Of course I didn't go into this thing blindly. I read up on all the most helpful tips and guides, including the amazing OkCupid blog, OkTrends (those guys are geniuses). Among other things, I found out the difference between the many pictures I have that were inappropriate and the two that were acceptable. I even figured out how to draw attention away from my more unsavory qualities...i.e. my three left feet.

And with that, I started messaging like a madman.

How It All Went Down

Ya see, I am generally not one for prolonged subtlety neither a fan of the super slow romance. So I spent a total of one week relentlessly bombarding women in my metropolitan area with whatever crackpot idea manifested inside my brain. I sent out such classic gems as:

In response to a girl who said she "wanted nothing better than to leave the Bronx, NY":

Me: "Personally, I'd leave the Bronx so fast the resulting echo from my sonic boom would drown out any attempt to say "goodbye". Your head would spin, your ears would ring (that's tinnitus y'all), and by the time I looked back the Boogie Down Bronx would have aged 30 years. I'd travel...see the sights...sell my own brand of flying car ...get filthy rich and seek out the most prime real estate in the country. And guess what, it'll be in the Bronx. Ain't gentrification a bitch."

In response to a profile named Princess Sunny who claimed she "liked every Jay-Z song ever made." I made a crappy poem (btw...bad idea), using the titles of Jay-Z songs (in bold) in every line of the 2nd and 3rd stanzas:

Me: "Amongst the NY dating scene, I sought true royalty by any means.
Her name was Princess Sunny see, the most beautiful of Astoria's Queens.
She has a laugh and zest for life, in effect making other maidens seem lazy.
Dissecting our interests with a knife, I find we both like Hova, aka Jay-Z.

It's a Hard Knock Life for singles like us, with 99 Problems put in our trust.
So Excuse Me Miss to be said this must, you've made my heart skip a Jigga What.
Good Girls-Girls-Girls are hard to find, whilst having an Empire State of Mind.
Yet she Runs This Town in her own sweet time, looking Young Forever..[blah, blah] red wine.

And on, and on.....

In response to a girl who wanted to know why "every single hip-hop song is about how snug the pants are 'cuz they be full of money.":

Me: During the 90’s and early 2000’s, baggy/saggy pants were of course…in vogue. Engendered by the national prison system’s “no belt” policy, made popular by such popular acts as LL Cool J, provided by fashion conglomerates such as Sean John and taken in a weird direction by 13 year old rap group Kriss Kross, the saggy pants style became the symbol of urban plight and struggle.

Six paragraphs later.....

So “money inside of snug pants” -- Is it the chest-thump grandstanding typical of most rap fare…yes. But it is also more evidence of an identity crisis facing hip hop and the newest artists to emerge. I’m really sorry about the length…I just get excited by this stuff. Ummm...No pun intended for that last statement.

Despite the weirdness of my messages, I got a reply rate of about 1 for every 6 messages sent. Not bad for a noob. From here on out it was simply a process of attrition. Which lucky lady could outlast my own special brand of soul-crushing neurosis?


A cute and supposedly curvy dentistry school student. From what I can tell she is on a mission to celebrate Halloween all year round. Her interests include improv, making random sketches, photography and occasionally satiating her dark side.

Me: (Commenting on one of her pictures) Ahhh....I get it. Your that blind girl from the Lionel Richie stalker training video "Hello". That is seriously awesome and you have a great profile. You don't have to say "hello," I'd be honored with even a simple "hi."

attackOftheScones: "Hello". I'm sorry, we're not on good enough terms for the casual "hi" to be used. I only say "hi" to people I've at least gotten to second base with. Until that point we are little more than strangers. Yet, I really appreciate that you figured out my costume reference. Until now it has sadly gone completely overlooked.

Me: Not until Second Base huh? Well what if I overshoot second base and get tagged out by the Yankees' baseman Robinson Cano.

attackOftheScones: What???

Me: Uhhh..Nevermind. Your 80's themed halloween costumes are really great...jerry curls and all. You must have put a lot of work into those outfits.

attackOftheScones: Thanks. It took me like four days to make each one. I'm really proud of them.;May I ask what you wore this past Halloween?

Me: I was a sad clown...a sad, sad clown. I drew a gigantic tear on my left cheek, sported a very convincing frown and carried around a broken party horn. Although, this year I'm thinkin' about being a 2nd baseman...wonk...wonk.

Me: Wait, sorry I mispelled "wink."

attackOftheScones: ...................................................

Me. Hello?



An interesting girl who I messaged solely because she posted one the most hilarious/disturbing dance videos that I've seen in a long time. (See Mortal Kombat Flash Dance here.) She is skinny, slightly goth and aspires to be a singer/songwriter.

Me: Holy Shit...when did my child hood heroes become Chip n' Dale strippers. Also, I think I frequent the deli in timeframe: 4:05 every other day. Never eating a banana from there again. Too funny. I also really like your profile.

mTrainDiva: Lol. Yeah, seeing that video always makes me laugh lol. Your so right, they are like male strippers lol. Whew...I'm still ROFL.

Me: Yeah I know right, Lol. It's like, what the hell are they doing? I especially like the "Liu Kang" guy, he's just crazy..lololol. Did I mention I really like your profile?

mTrainDiva: OMG...the Liu Kang guy is my You have to give him props though...he really knows how to work Sorry I've still got the giggles.

Me: Yeah...yeah, me too. I'm still ROFLing my brains out. L.....o......L. So what are your interests?

mTrainDiva: Also my boyfriend totally said that we are totally gonna dress up and do this same exact thing one day. I can't wait, lol.



This online vixen had one of the best profiles i had ever seen. On top of being a left-handed violinist with grapheme synesthesia (look it up), she was a dog lover and sports fanatic. And her looks...just imagine curly red hair nestled just past the shoulder, gently cradling the most alluring face you have ever seen. By just reading her profile a strong feeling welled up inside of me...was this <3.

Me: (Commenting on something in her profile) So I see that you used to work for the Suicide Hotline. You've gotta have some interesting stories. Ever talk someone down from the edge of a building.

queSaraSara: Unfortunately no, but I did stop a single mom from drowning herself once. It's probably my proudest moment. To be honest, ninety-percent of calls to the suicide hotline are creepy requests for phone-sex from the broke and desperate.

Me: God your awesome. May I ask how in the world you are single? Not that I'm scoping for character flaws or anything, but feel free to mention any daddy issues, nervous ticks, or psychotic breakdowns.

queSaraSara: I am sane, smooth and my dad is a could you. Just kidding lol.

15 Messages Later.....

Me: Ok we've been messaging each other for forever and a day. You've managed to stick with me, even through my weirdest tangents and sidebars. So how about we take this to the next step. Can I Ha Yo Numba?

queSaraSara: Alright. I think it's about time. Here it is: (417) 568-0098. Call me in the evenings before midnight.

Me: Score!

Lessons Gleaned From This Experience

  • Good online dating is a process. At least with some women, you can expect to exchange a ton of messages before they agree to take things further. And with that said...
  • Don't get hung up on one profile. If your advances get rejected or she/he stops replying to your messages...don't fret. There are plenty of fish in the digital sea. In fact, you should continuously message mmm...5 profiles that hold promise for an actual date. Why, because 4 out of 5 times your efforts will probably fail; primarily because of this next item...
  • Both men and women are flaky when conversing with other singles online. I am speaking from a man's perspective, but I'm sure you ladies can relate. Dropped conversations, unanswered calls, being stood up on dates; the rules of social etiquette simply go down the shitter when the internet's involved. Oh yeah and don't forget that you should really...
  • Try to update and improve your profile continuously. Beyond your messages (which I'm sure are awesome), your profile does a lot of the work for you. Believe me when I say there are those who can't string two sentences together but because they have such excellent profiles, they get tons of messages.
  • Location, location, location. I can't emphasize this enough. To be most effective, you should really message/woo profiles you like most a 25 mile radius of you. The truth is many women on these sites are skittish about meeting a complete stranger, much less someone who is more than a short drive away from them. True story: I once knew a guy who went out to Oregon from the East Coast looking for some girl (in her late twenties) he met online; turns out "he" was in his late fifties.


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    • Justin Muir profile image

      Justin Muir 5 years ago from New York

      Your absolutely right My Minds Eye53. Despite my very best writing, I found it very hard to keep anyone's attention for very long. I would say it's about 50/50 fiction to non-fiction.

    • Justin Muir profile image

      Justin Muir 5 years ago from New York

      Thanks for the vote up Natashalh. Glad you enjoyed it.

    • Justin Muir profile image

      Justin Muir 5 years ago from New York

      Thanks carolinekirby, personally I found OkCupid to be the perfect venue for my wacky musings. It was all good fun.

    • Justin Muir profile image

      Justin Muir 5 years ago from New York

      Thanks Helena. Psychotic indeed. Thankfully I've met more interesting than the latter.

    • My Minds Eye53 profile image

      My Minds Eye53 5 years ago from Tennessee

      I found your hub very funny and that first photo hilarious. The trouble with on line dating (besides the obvious, not knowing who you are really talking to) is that if they find one tiny thing they don't like or if you hesitate, they have gone on to someone else. Like in real life, you have to invest some time to get to know someone and it doesn't happen there.

      But having said that I enjoyed the male point of view and hope most of it was fiction. Voted up.

    • Natashalh profile image

      Natasha 5 years ago from Hawaii

      Super funny read! Voted up and funny because I had a great laugh.

    • carolinekirby profile image

      carolinekirby 5 years ago from Indianapolis, IN

      Great article! 1 out of 6 replies isn't bad for a guy, since most women get at least 20 messages a day (at least in my experience!)

    • Helena Ricketts profile image

      Helena Ricketts 5 years ago from Indiana

      This is good & funny stuff! I did the online dating thing for a while before getting married a couple of years ago. You definitely meet some really interesting and sometimes psychotic people that way.