My Guide To Initial Messages For Online Dating


I’ve been trying out online dating for the last few months and the hardest part by far is after reading somebody’s profile, figuring out what to say in an initial message so they will respond back.  Here are my unedited attempts.  It probably would have helped if my whole online experience didn’t collapse into me just entertaining myself.      

Attempt #1: My first attempt felt too serious and long.  I did think that the inclusion of a riddle at the end was clever.   

I’ve always found people with artistic skills fascinating. It’s probably because no matter how hard I try I’ve never had the skill to create in any medium what I see in my head, which I find frustrating. I have however, slowly over time taught myself to take photos, mostly landscapes, and have had some some people complement my them. Though my photos seem more like recognizing an opportunity when I see it rather then any kind of artistic talent.

I’d like to say up front that I really don’t feel like my profle represents me as well as it could, though I’m not entirely sure how to correct this, yet. There’s a lot of different facets to me and it takes time to reveal all of them.

All that being said I’m sending this because you seem like you’d be an interesting person to talk to and get to know. I imagine you get a lot of messages so I should probably write something enticing or witty, but I’m fairly tired right now and nothing is coming to mind. I could probably force something, but it would mostly just be bullshit.

Anyways, if you have any interest in getting to know me better, message me back.

P.S. How far can a dog run into the woods?

Success:  Unsurprisingly, no.  She probably didn’t know the answer to the riddle.  Also apparently, reading back over my message, I’m terrible at spelling and grammar.      

Attempt #2:  My second attempt still had me pretending to be a normal person.  Though I did try to make it more interesting to try and start a conversation.  I also attempted to proofread better.

I am severely disappointed in the total lack of flying cars. I feel like this is something we were promised the 21st century would have, and that science and industry just let us down. Don’t get me wrong, I do love many of our achievements, but c’mon, flying cars.

One of my favorite book series is the Mars Trilogy by Kim Stanley Robinson which outlines the colonization and terraforming of Mars. If I had a chance to join some kind of Mars colonization effort, I would do it in a heartbeat. Keeping my fingers crossed on that one.

Success:  Oh hells no.

Attempt #3:  I should probably first mention that this woman stated in her profile directly that she wasn’t on meth or something.  She also bragged about how long she could tread water and that she could knit.  

Congratulations for not being on meth or something. That overall seems like a positive.

I can tread water for 30 minutes, would this be long enough to be competitive or should I start some kind of water treading training program with a Rockyesque montage?

Also, knitting is pretty good, but crocheting is more bad ass. Not judging, just saying.

Success: Strangely enough, this one worked, I got a response.

Attempt #4:  At this point I decided to try extremely short messages.  Putting them on the defensive probably wasn’t a very good idea.  Judging by this gals profile, she would have married her dog if it was legal.   

This is probably a horrible way to start a conversation, but I’m wondering what makes your dog so special and unique? Looks like your everyday Aussie Shepherd/Blue Heeler mix to me.

Success:  I never got to find out what made that damn dog so special.

Attempt #5:  This lady had some wise crack comparing her iPhone to using carrier pigeons.  This one kind of got out of hand but I couldn’t help myself.  She was also one of many women to talk about their unique laugh.

I really think you should reconsider carrier pigeon based communication. What a carrier pigeon loses in speed it more then makes up for by being a green technology. Just imagine a world where instead of showing off your new iPhone or Android, you show off your new speckled red crested pigeon, you’ll be the envy of all your friends. Plus you get the two side benefits of entering your pigeon in the lucrative Chinese pigeon races (yes, this is a real thing), and putting Pigeon Fancier (one who trains pigeons) on your resume. Really seems like a no brainer to me.

Not to get off the topic of pigeons, but I was wondering what makes your laugh so unique and noticeable? Is it one of those tinkling of heavenly bells laughs, or are we talking about one of those Santa Claus has had way too much eggnog belly laughs? Both are fine, just curious.

Success:  She probably got too excited about buying carrier pigeons to have time to respond.

Attempt #6:  This one talked a lot about her favorite color being green.  I made up the friend in a little white lie.  Not saying I don’t have friends, just not any with that much interest in the color spectrum.   

What about teal? I only ask because a friend and I recently got into a debate over whether teal was a shade of green or a shade of blue. Not to put pressure on you, but your profile does suggest you’re some kind of green expert, and there may be a substantial bet of $5 riding on the answer.

Success:  This one worked.  It always help to get them talking about what they know.

Attempt #7:  I will say that I’m pretty sure I was slightly drunk or something when I wrote this one.  I do know that by this point I was getting a little frustrated with the whole online dating thing and never knowing what to write.

So, when you say you enjoy scaring the crap out of yourself while watching horror movies, do you mean that figuratively or literally? I’m only asking because I recently got a new Ikea couch (note the subtle hint that I have exquisite taste in furniture) and there is only so many times you can flip a cushion. Plus getting out to Ikea just to buy new cushion covers is a bit of a pain in the ass; what with the drive, the meatballs, etc. Now there are always exceptions, but in general I’d say I consider defecating on my furniture a deal breaker.

However, I really have no problem with you peeing and throwing up on yourself while riding a roller coaster. I’m fairly classy and wouldn’t even do the whole pretend I don’t know you thing. Nope, I’d walk proud with you through the amusement park for the rest of the day. Though I’d probably leave my window down on the car ride home.

Success:  For the safety of my furniture and car seats its probably better that someone who stated that they like to scare the crap out of themselves and pee themselves on roller coasters did not respond back.

Attempt #8:  This woman had on her profile what her high school class had voted her most likely to do.  She was 27.  Also she seemed to have a fascination with the movie Clue.  I did not put in a lot of effort on this one.

Sure you were voted most likely to go sky diving, but did you actually do it?

I’m fully with you on Clue being a great movie, one of the more under appreciated ones in my opinion. Which was your favorite ending?

Success: Again, pointing out people’s flaws is probably not the best way to get them to talk to you.  But then again, if they’re bragging about being voted most likely to go skydiving in high school, and never do it, they probably don’t have good follow through anyways.

Attempt #9:  This woman seemed to really enjoy running and drinking, so I thought the least I could do was try and introduce her to the world of the hash house harriers.  I hoped that insulting myself a little might get a sympathy message.

Sometimes when I’m using this thing I get an uncomfortable sensation that OkCupid is far too similar to buying a car stereo off of Amazon. Really all its missing is just a section for comments from other people who have tried the “product”. These are the times that I wonder how somebody talked me into trying this thing.

Lets face some facts. Your an attractive woman who seems to have an interesting personality, so I imagine you get a large number of messages from random guys, of which a creepily large amount contain pictures of abs. Given this sheer volume little old me doesn’t stand much of a chance of being noticed, especially since I am not gifted with the ability to start a conversation via email. I propose that, if you’re in anyway interested, we cut all this crap and just get a happy hour drink sometime. At worst you lose just an hour of one day of your life.

Irregardless your above desicion. After perusing your profile I picked up a few hints that you like to run, explore Portland, and inbibe in alcoholic beverages. I guess I’m a regular Sherlock Holmes. I belong to a drinking/running group called the Hash House Harriers and I think it might be something you’d be interested in. We meet up several times a week to have a few beers, go on a run, and generally just have a good time. The two big selling points are each time it starts in a different point in the city, and only one person knows where the run is going to go. If your interested check it out


P.S. Kudos on looking good enough in a lavender bridesmaid dress that the dude on the motorcycle stopped to check you out.

Success:  In retrospect women rarely liked getting compared to car stereos, even highly rated ones.  I still think she would have made a good hasher.    

Attempt #10:  This lady seemed very concerned over the possibility of a zombie apocalypse.  Knowing that women like a man that makes them feel safe, I wanted to convey that I was a man of action with a plan.

I believe that everyone needs to have a zombie apocalypse escape plan. If year’s of watching public service announcements has taught me anything, its be prepared.

My zombie escape plans involves an armored bus carrying at least 15 survivors with very mismatched personalities to the area of the state with the lowest population density. I envision it to be similar to MTV’s Road Rules, only with zombies. I estimate that in our journey at least 5 people will die, 3 being minor characters, 1 being a major douchebag who hides the fact that he’s been infected, and 1 being the most skilled character who has shown the most heroism and wisdom during the journey. When we build our new utopian city, we will name it after him/her.

Success:  It worked, this one did reply.  Probably because I was humble enough to not name the new utopian city after myself.

Attempt #11:  This woman’s profile seemed to talk about slug sex quite a bit.  It seemed like this was a perfect time to show off my vast knowledge of gastropod coital rituals. To help seal the deal I included a clip from Isabella Rosellini’s “Green Porn” which explains how different animals mate.   

Who isn’t amazed by hot slug on slug action? Though to be honest, I have been a little traumatized since I learned that sometimes they chew each others penises off. However, regardless of my personal feelings I remember seeing the below video link on the subject and laughing my ass off. Enjoy.



Success:  She must have already known all my slug sex fun facts and decided I had nothing new to offer.

Attempt #12:  I actually enjoyed this gal’s profile.  She seemed to have a good head on her shoulders and a realistic expectation of what a relationship entails.  I should also probably mention that her pictures were one of her wearing deer horns, one of a machete, and another of a stack of beer cans taped together (aka a wizard staff).  

Referring to what your wrote for the most private thing you’re willing to admit, rock on. After reading it, and looking over the rest of your profile, a voice in my head said to me, “this woman obviously has her shit together, you should message her.”

“But what the hell would I say?” I asked.

“You’ll figure something out,” answered the voice, “just be honest and straightforward. Also probably avoid making the obvious nice rack joke.”

“C’mon, it would be hilarious.” I said.

“No,” said the voice forcefully, “if you want to say something about her pics complement that sweet ass machete she has, or ask her how tall she managed to get that wizard staff.”

“That is a pretty rad machete.”


Anyway, that was the inner monologue that led to me sending this message. Maybe its a little too much for a first time message but I hope you at least get a laugh out of it. Though I would still like to know how tall that wizard staff got?


Success:  It worked, I got a message back and we had a nice long conversation about wizard staffing.

Attempt #13:  This girl’s profile entertained me.  She bragged about being able to give good airplane rides (holding up someone laying horizontal with your legs) and she also had a crazy made up story that she was going to be competing in a llama wrestling match, which apparently is more of a staring contest than an actual grapple.  

I started writing this only hoping to score some sweet airplane rides, but then I read the rest of your profile.

Good luck to you in your upcoming Llama Wrestling competition with the unfazeable Mr. Professor. He’s a dangerous opponent, and probably one of the greatest llamas to ever participate in the sport. I remember watching him during the ’07 World Championship in Helsinki. He and Felipe Rostov, the reigning champ at the time, battled for over 14 hours. Finally Mr. Rostov fell over dead from a brain aneurism. For god sakes, be careful.


P.S. Also congrats on your fine work bringing back the word heiney.

Success:  No response.  Maybe llama wrestling is a real thing.  Also she was probably crazy.

Attempt #14:  A woman talking about Urban Iditarod!!  This one seemed like a no brainer so I kept it simple and tried to hide the fact that I’m weird.  

Realistically what kind of people haven’t heard of Urban Iditarod? I’ve done it twice so far, once as part of the Venture Brothers team and last year as part of the probably entirely inappropriate Whitney Houston pallbearers team. What about you?


Success:  It worked.  I got a response.  All hail the power of the Urban Iditarod.

Attempt #15:  I was getting fed up again by this time.  She said she liked poetry so I wrote her a haiku.  Felt pretty clever about that one.  Also she said she wanted to go on a treasure hunt and liked to talk about sociology.

How do I stand out,

Just one more face in the crowd,

But so very much more.

I do not have a treasure map…yet. But I have been working on piecing together clues from old Oregon Trail journals to try and find the lost Blue Bucket Mine. This is just one of the many brands I have in the fire.

I also enjoy a talking about societal structures and theorizing on why things are the way they are. Unfortunately its often hard to find people who want to talk about such things, especially if the two of you disagree. This seems funny to me since listening to dissenting opinions is often the best way learn.


Success:  Apparently my haiku sucked.

Attempt #16:  She had a lot of song lyrics on her profile, including part of a song by the Doors.  I thought it was clever to put in the next few lines from the song.  She also talked about how to make lemonade by letting lemons mold.  I was trying to be casual and nonchalant.

I see you live on Love Street

There’s this store where the creatures meet

I wonder what they do in there

Lyrics from The Doors and promises to clean my fridge to make moldy lemonade. How could I resist?

My day has been a little strange. It started out normal enough with showering, shaving, eating breakfast. But then I left my wallet in the refrigerator and it has all just kind of gone downhill from there. Now here I am, wasting time, perusing the internet.

Anyways, I should probably get back to work. Message me back if you want to.


Success:  Nope.  On the lighter side I won’t have to try lemonade made out of moldy lemons or constantly sit around with someone who quotes song lyrics to describe themselves.

Attempt #17:  This woman had a pretty good profile.  Part of it included making a “Clue” joke that she killed a man, with a pipe, in the conservatory.  She also seemed pretty proud of her MarioKart abilities and had a picture of her brandishing a X-mas tree like a weapon.

Damn it, I was guessing in the billiard room with the wrench, boy was I off.

Anyways, though I am no expert and I’m absolutely not licensed in any way by any credible institution or organization, I believe I can provide suitable answers for all of the things you spend a lot of time thinking about.

You should eat food for dinner. In order to stay healthy you should avoid eating plastic fish, they are not food and present a choking hazard. The best way to get around town without a car is to learn how to fly. Learning how to fly is easy, you just throw yourself at the ground and miss. The best way to get out of town without a car is to hitchhike with truckers, they always have interesting stories and only 1 in 10 will probably murder you. For second dinner you should probably stick with food, though moss is a suitable substitute if you want to mix it up a bit. Luckily Portland has no shortage of moss, and its all organic. Thinking about your loved ones is good, though if you really cared you’d probably offer them some of your primo locally grown organic moss.

I hope this helps.


P.S. Not to brag, but I could probably kick your ass in Mario Kart, except for Rainbow Road, that level is seriously screwed up. However, you probably have me beat in the ancient art of beating the crap out of people with Christmas trees.

Success:  Despite my best attempts it worked, and I even got a pretty witty response back. Of course, she may not be actually making a reference to the game Clue, and may just be trying to murder me.

Following my first seventeen attempts I decided to take a little hiatus and not suffer the constant pain of rejection for a little while.  All in all it wasn’t a bad experience.  It did result in a couple of dates, but the entire exercise felt decidedly strange.  

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