The Countdown

Well, Lent begins tomorrow. Bloody hell.

Something like this, with a
calendar and a pen under it.

I’ve booked two safe daytime coffee dates with strangers (Constantine and Dennis), I’m hoping for a sporty date on Saturday (with Mark) and after that, I’m totally stumped. Did I actually expect to write dates in my calendar every day and just wait for men to magically appear and have everything line up perfectly?

Yes, I did. Call me an optimist or an idiot; that was what I was genuinely hoping for.

It turns out that finding men, talking to them, arranging life and logistics is actually rather difficult. Lent hasn’t started yet, but the number of times I’ve thought, “This is exactly/probably why I am single!” is in the double-digits. *

*Side challenge: if someone wants to take me up on this, we should get together after Lent and have shots for every time I say a variation of "That's why I'm single," odds are pretty good I’m going to need help drinking them. Who’s in?*

Not that I’m throwing my hands up in surrender, there are a lot of things I’m really psyched about. For one thing, the strange guys seem quite nice.

Constantine

Not much into speculative fiction, so odds are he’s not a Harry Potter fan, but Constantine is definitely a fellow Ravenclaw. His online dating profile contained not one but two (2) words I had to look up. Yay! He listed “semantics” as one of his interests where most guys put “beer” or some combination of “hiking” and “watching Netflix.” Semantics is at the heart of my undying (and some say unrequited) love of puns, so this could be the start of something punderful. We may also be dealing with a fully-fledged intellectual type. Not sure I will be able to keep up, but I will try!

In one of his profile photos, he is holding a small bird and taking a photo of it with a fancy camera. From this, I can conclude that he is either magical or can speak fluent chickadee. Impressive either way. We’ve exchanged emails, and (per my request) he sent me some of his essays to read. Such are my skills at flirting (which is probably why I’m single). *shot*

Illegible speech bubble says:
"I don't need to read about wizards. I freakin' am one!

Dennis

I know absolutely nothing about Dennis whatsoever. No photos, no essays, just a couple of amiable-sounding texts to give me an indication of the person on the other end. I am picturing just a question mark with glasses, a collared shirt and sneakers. I am sure I will recognize him immediately as the guy with the eyes and nose and stuff. I got this!

Mark

I also know absolutely nothing about Mark. And from this vacuum, I decided that Mark and I should go watch sports together as our date. I didn’t ask him out for coffee or anything. Maybe it was his name (which isn’t Mark, and thus isn’t helpful for you, sorry) that made me decide to change the variables. No coffee shop vibes and idle chat with Mark. We’re going to do something different, a little more fun. Maybe because I've pre-emptively decided that Mark and I will be friends.

It also seems like I’m getting the hang of the dating person’s thought process. A teammate introduced me to a guy on Sunday and my first thought was “How do I ask him out?” versus my usual, “How am I going to use the leftover cream cheese from my Saturday baking frenzy, and why is what’s-his-lips looking at me like that?” I didn’t actually manage to ask him out, but I thought about it. Small victories, people!

Do we have time for a parade?



There's always time for a parade!

Trying not to overthink my first first date tomorrow.

It’s going really well (the not overthinking bit, that is). Because I’m a rational person who doesn’t perseverate over things I cannot control. Not at all. Nope. I haven’t even begun to spin bizarre and unpleasant scenarios that could unfold. I didn’t imagine Constantine pretending not to see me or faking instantaneous macha-latte-induced food poisoning just to escape. I also didn’t play out the scene of me tripping over my feet and sprawling face-first into a trendy little table, smashing out both of my front teeth. I have not been hearing the press of awkward silence as I fumble for something to say. I definitely haven’t been looking at the price of plane tickets to Borneo. I have just been allowing time to pass naturally. Tomorrow is just another day. And I am just a normal, well-adjusted girl. Obviously.

Bring it on.

Finding 40 Dates: Part Four - With a Little Help From My Friends

After going out on that first limb and texting Mark, I thought I could rest on my laurels for at least a few days and just ignore the impending onset of Lent and everything that goes with that. Foolish mortal. Luckily my friend who started this whole fiasco was hosting dinner before our volleyball game last night, and the girls convinced (I think the technical term for it is “peer pressured” but this sounds more grown-up) me to write a few more messages to strange men.

I logged onto the online dating site and we all crowded around my friend’s laptop to sift through the profiles of some of my best matches. I didn’t realize that the profiles I’d been looking at thus far were mostly random-generated or more likely chosen for unfathomable self-interested dating site reasons. It turns out there is a place to go to find the people who have compatible profiles to mine. This is where we went. To our credit, we didn’t spend too much time making lewd comments (probably because we didn’t want to be late for our games). The five of us crafted a few messages which made for some great laughs and really expedited the entire process. Collaboration is more than just an overused corporate flavour-of-the-week word. It would have taken me days of agonizing to write those few simple lines. When I hit ‘send’ we actually cheered. Girl friends are the best.


Squad Goals

Between games we checked my phone. I don’t usually do that, because most things can wait until after I am done playing volleyball. The girls candidly informed me that this could not wait. The little red light on my phone was having a conniption fit. I had received a text message from a friend-of-a-friend who heard about the 40 Date Challenge and “thought it sounded like a fun idea!” I blushed crimson and quickly set up a date with him - let's call him Dennis - for next Thursday. Then, what the crowd was waiting for: of the three messages I’d sent, two of the guys had written back. I couldn’t view the messages immediately (Alec, my Blackberry is delicate about things like emails with links to websites that he doesn’t trust), so we waited until after our second set of games before one of the girls handed me her smart(er) phone and I logged in and read the replies. Out loud. There was squealing and hand clapping and to my endless delight one of the girls actually shouted, “We’re going to be your bridesmaids!” It may be the girliest thing I’ve ever been a part of (and I’ve actually been a bridesmaid a few times) but it was lovely. 

A nudibrach.
Photo credit to Jerry Kirkhart
Other credit to Constantine for teaching me what one was.

I’m quite excited (and nervous) about the guys that the internet chose for me so far. Constantine is verbose, imaginative, and odd. His username was an obscure term that I had to look up and means the joining together of two independent principles into a strong conclusion. Deep. I think he would be great to sit and visit with, which is the plan. Another guy’s profile pic showed him in a kitchen, elbow deep stirring a massive pot which I assumed contained spaghetti sauce (no idea why) and is now commonly referred to as Spaghetti Guy. He seems like he would complement my strengths and be fun to be goofy with. His ideal first date is sampling free food at Costco, which is bizarre. The third one hasn’t replied, so I have forgotten that he exists. It’s easier to overlook the minor things that I’d normally worry at when I write to more than one guy at a time.

I haven’t heard back from Mark yet about setting up a date, but I think the next time I text him it won’t be quite as arduous. I hope.

Nicely done, Guy Incognito.

Went for lunch with another friend who also made me sign in on his smart(er) phone to read (again, aloud) the message that Constantine sent me this morning. My friend has also expressed a fervent interest in tagging along and observing my date with Constantine. He offered to wear a fake moustache or hide behind a newspaper to be more discreet. Classy.

Overall, I have decided that the worst thing about the dating thing is the fact that we suffer through it alone. Not the dates themselves (hopefully) but all of the stuff that leads up to them. I’m truly grateful that I don’t have to. My friends will get me through, and make it a hell of a lot funnier.

Finding 40 Dates: Part Three - The Plunge

I honestly can’t remember the last time I asked a guy on what could reasonably be construed as a date. I’m either the askee, totally oblivious, or just hanging out with friends. So this is definitively uncharted waters for me.

Might explain why I’m super nervous, and why I’ve been in procrastination overdrive all week.

Today my big delay has been because the website with my volleyball schedule has been down and I can’t possibly plan dates if I don’t know when I’m supposed to be playing next week, right? Right.

Must be another sign from the Universe. Can’t ask out boys today.

Phew.

It’s not like we’re dealing with deep-seeded trauma here.

Oh no, not the boner brushoff!



Ok, so in eighth grade I finally plucked up the courage to ask Ryan Jones to dance with me and he said, “No way, I have a boner.” I don’t imagine rejection gets much more awkward than that. But it seems like I haven’t asked a guy out since. If I have, I don’t remember it. But as far as these things go, getting the boner brush-off isn’t really all that bad. It’s far funnier as a hazy memory of junior high school than it felt at the time.

After mulling over trauma, rejection and life, laughing at my junior high self, and then freaking out a bit, I texted Mark.

Mark is a friend’s boyfriend's friend. Obviously. I received his number from my friend with the caveat that he already knew about my Lent resolution and had offered to be my date every day, if necessary. This was mostly scary as opposed to reassuring. Pretty sure she built me up as some sort of goddess. I know absolutely nothing about Mark; I presume he has an abnormal amount of time on his hands and a charitable sense of humour. But it is entirely guesswork.

I texted a stranger and asked him on a date. Weird.

My hands are clammy. Were they like that before? Are they always like this? Why have I never noticed?

Sweet Jesus, this is now totally outside of my control. And best-case scenario, I have to do this 39 more times. That is assuming that no dates fall through or cancel or say “no” or just don’t ever reply and leave me in this strange new limbo with clammy hands.

Oh what fresh hell is this? He has replied to my text.

Don’t freak out. Don’t freak out.

I have read his message several times and can’t really understand it. He writes in full sentences though, which is a plus. I presume my reading comprehension is compromised somehow. The gist is that he will check his calendar and get back to me. I think if he had written “No way, I have a boner,” I might have laughed hysterically until I passed out. Is that what I was expecting or afraid of? Not sure.

I think it’s mostly a fear of the unknown. And of being vulnerable.

I can’t believe I am going to have to do this again. Deep breath.

Finding 40 Dates: Part Two - Procrastinating

What is Borneo?

One evening last week I made myself a hot chocolate and settled down to write letters to strange internet men. Just as background noise, I turned on an episode of Jeopardy. Since you ask, most of the storage space on my PVR is taken up with episodes of Jeopardy, which I love beyond reason and prefer to watch sporadically and only with people who are comfortable with me shouting out my responses (in full question format) which vary from exactly correct to wickedly profane to utter nonsense. I tend to skip the interview bits where you cringe at just how inane super smart people can be. But it’s good to have on in the background while puttering around. I like to think I pick up some really good bits of trivia just from ambient listening. This is important to my life because you never know when you might need to know where Borneo is.


I fired up my laptop, and while it was starting I flipped through a cookbook for cupcake recipe ideas. I was getting ready to participate in a cupcake bakeoff and would need to come up with something brilliant to topple the reigning bakeoff champ. (Remember that bit about going all-out? Yeah, it’s how I roll.) Some of the recipes involved making ganache, which was new to me. To make ganache, you pour heated cream over chopped chocolate. The kind of cream that my recipe book called for was “heavy cream” though I’d never heard of that before. Luckily my computer had booted up, so I was able to look up the difference between heavy cream and, say, whipping cream. The fat content of heavy cream is 36-40% whereas whipping cream contains 35% fat. Who knew!? If it comes up in the double jeopardy round, I’m gonna be all over it.

An email notification reminded me that I was supposed to be writing replies to any and all literate potential dates. I read some new ones (a few that just said “Hi” and one scarily thorough 2 pager) and refreshed my memory by re-skimming the profiles of the ones who made the cut. I came to the conclusion that men who are interested in me are (generally speaking) categorically unattractive night owls with alopecia. Nevertheless, I need dates for Lent. I took a composing breath, almost unconsciously shouted “Who is Lehane?” at a recording of Alex Trebek, and hit the reply button. At this point, my computer gave up. A sign?

Earlier that week we had some fine cable gentlemen come to our office to fix something internetty. While it was down, the newest office intern revealed a Google Chrome game involving a dinosaur that pops up when the internet isn’t working. Kids these days.

Me as a Jeopardy contestant.
An extremely necessary use of my time.

So when I hit ‘reply’ and the whole online dating conundrum disappeared to be replaced with a low-tech, offline dinosaur game that I’d heard the cool kids talking about, I had to try it out (instead of restarting my laptop and the modem and whatnot). It’s not procrastinating. It’s a game. Right?

It took a while for me to get bored of it. By that time, I was on a whole new episode of Jeopardy and the contestants were terrible. Then I realized they’re just lovely geeks trying their best and I was probably just hungry. I restarted my computer and went to make myself a snack. While figuring out what I wanted to eat, I made a list of cupcake ingredients I would need for a few different potential recipes so that I could see what I already have in my kitchen and thus know what I would need to buy tomorrow. I made popcorn, wrote lists, yelled at Trebek, turned on some Motown, forgot all about making dates and went to bed.

I think next time I'm online I should amended my profile to include that my ideal man is patient. Or at least, he should try to be. I’m sure I’ll get around to making 40 dates very shortly thereafter.

Have you ever noticed how writing a blog is practically the same thing as writing awkward introductory letters to strangers? Me neither.

Finding 40 Dates: Part One - Hi

Nevermind, call off the search. I've found the perfect man!

Want to know how to effectively terrify someone who is relatively new to online dating? It’s dead simple. Let them sign up, give them a few minutes to acclimatize, and then send them 25 emails overnight. Waking up to an inbox full of messages from the sleepless, lonely internet is incredibly daunting. So in order to not feel overwhelmed, I ignored them. There are 34 more of them now. Not very whelming.

So, time to start sorting this mess out.

“Kloe69 just sent you a new message at 11:37:47 PM on Sunday, February 12, 2017 (Pacific Standard Time)!”

Where do I even begin?

Bad sign

Good thing they told me it was 11:37 and 47 seconds. Specificity is critical. That’s how I know that Kloe69 isn’t the one for me. I prefer people who send emails in either the first few seconds of any given minute, or alternately the penultimate second. It shows depth of character. Good thing each of those seconds was noted and accounted for. The username is a whole other mind-boggling kettle of fish. Admittedly, I am usually the first one to giggle when the scoreboard reads 6-9, but seriously Kloe, get your shit together.

Great sign

And I haven’t even gotten to the content yet! Drum roll, please…

Hi

Really? That’s all you’ve got to say for yourself? I find it even more baffling considering my only request was literacy. Maybe it’s just a jumping off point. Maybe Kloe69 is just getting warmed up. It’s my first email and already I’m wavering on my only standard. Bad sign? 


Well, I made it through the barrage of bad emails. Most of them were along the same lines as Kloe69, which is nice because they don’t take very long or (to my mind) require a response.

There was maybe one that I am inclined to reply to. According to a friend, this means that I must reply to at least three. Got to account for the fact that I'm not naturally into any of this stuff. I checked out the profiles of everyone who sent me a message. One of my personal favourites (Grandami) wrote the following in the blurb on his profile:

Hello guys hdjjdi idkcm c Judie,skiff ncjkslskvj mdkdkjfif kfkk[.]

What the-actual-balls is that?

Judging by the wonderfully specific notation of the time of each of my messages, I have determined that my profile resonates best with either people (and I say “people” instead of “men” on account of a few questionable profiles and one definite woman who reached out to me) who are online very late at night, or perhaps my profile becomes more attractive the later it gets.

Morning people don't seem to appreciate me much. I've decided I'm ok with that.

I did get one compliment, “You have the most incredible smile!” Pretty sure that same comment has been copied and pasted into a dozen messages to other women. Still, it kicks the shit out of “Hi.” I am frankly amazed at how few men measure up to the standard of literacy. I’m not looking for iambic pentameter or a thesis paper–just a subject, verb, and object to begin with. I did not think it would be such a tall order to fill. The wonders of the internet never cease.

One ray of light is the 34-year-old guy who actually quoted part of my profile to me and asked a relevant question. His profile is not particularly inspiring. He is prone to comma splices, and his Virgo personality will probably aggravate mine, but a girl doesn’t accumulate 40 dates by demanding so much more than basic reading comprehension.

So I guess the next step is to respond to those guys who strung together an entire sentence, and maybe send a few unsolicited messages of my own. There will be some ranting, neuroses and liquid courage involved, so stay tuned for how that goes.

Profiling Like a Pro

If I’m going to do this thing right, I will have to set up an online dating thingy.

Ok! I have a massive cup of tea, my keyboard at the ready. Time to make a profile. Should be fairly simple, right? There are 89 zillion people on dating websites and apps. If they can do it, so can I.

Famous last words: "Hold my beer; watch this!"

The first priority for me here is honesty. I will be as forthright as possible, even as I imagine each of my answers being met with red flashing lights and a massive server somewhere grinding to an exhausted halt.

Basic Information

I totally rocked the basic demographic stuff. I am a woman *click*, I am looking for a man *click*. Barely tempted to lie about my age. I decide that anyone unwilling to check the 30-35 age range is a coward. My first defensive thought. On we go!

More About You  (Because who doesn’t like that?)

Tea is long gone. I took a quick break for a grilled cheese sandwich, and am back at it.

Now a more involved bit where I am asked to determine how I would describe myself. This involves a lot of personal information. Surprised they haven’t asked me when I ovulate or what my farts mostly smell like. Has the internet figured out that women fart yet? Note to self: Don’t write “fart” in your profile.

I made it through without making anything up. I shut down my mischievous impulses and I did not make up an Australian persona who looks like me, but is vastly independently wealthy, owns a baby sloth sanctuary in Cost Rica and spends her free time paragliding and base-jumping. Nope. Just stuck with reality. Grown-ass woman in the 30-35 age range. Yup.

Ok, so I was being flippant earlier about how in-depth they were getting. I think there are some key areas that they missed out on in the ‘more about me’ section.

“Excuse me, Dating App! In addition to my blood type, the depth of my palmistry lines and my nearsightedness, you should also know that I got sorted into Ravenclaw house, and my patronus is a marsh harrier, though I had to look up what that was (a bird). I had my wisdom teeth out in 2005, my paternal great-grandfather worked in an Irish whiskey distillery, and I once had an allergic reaction to bee stings but that may have been the number and concentration of them so I don’t carry an EpiPen. I’m sure that will help you find me a compatible personality on an interweb filled with liars and deluded weirdos.”

Ok, starting to get a little jaded. But we’re nearly done, right? Right? Please?

Your Profile Photo

What do you mean you don’t accept an out-of-date drawing of what I would look like as a mannequin-style puppet? Fascists!

Time to switch to whiskey. With rocks, because it’s the afternoon and I’m a classy gal.

Phew! Good thing they have this handy little advice popup. So I’m looking for an acceptable photo of me that:

1.       Doesn’t feature a bunch of my friends who are better looking than I am (Why are all of my friends total babes? Easy for you to say, internet. Apparently I don’t roll with anything less than an 8.5);

2.       doesn’t feature any guy friends who might be mistaken for an ex-or-current-boyfriend (Even my dude friends are babely);

3.       doesn’t highlight any of the features I don’t particularly like about myself;

4.       is recent (although I’m reasonably certain that the best-ever photo of me was taken when I was seven); and

5.       Shows my face without aviator sunglasses, a mask, a wig, a fake moustache or a purposefully ridiculous underbite.

Seriously.

2.5 hours later… Still looking… No, that’s a cartoon of you as a mannequin-style puppet that you drew two years ago. The onlines say you can't use it. I like it too, but we’re weird. We’ve also been drinking a little, so we shouldn’t trust our judgment.

Big glass of water. Some juggling. Literal juggling, not just opening up an unnecessary number of browser windows to give myself a feeling of false accomplishment. Ok, did that too.

The Blurb

Oh good, writing! I can do this. I write all the time. I write for fun. Writing is fun!

Except it’s supposed to be about me. Cue the identity crisis. What can I honestly say about me?

1.       I am a good-ish person. I know this because some of my friends told me so;

2.       I like many things. Though I can’t remember what any of them are;

3.       I am not hideous. I know this because I survived childhood with only my brother ever saying so;

4.       I am generally reasonable. I need no evidence of this, it is so;

5.       I am funny. Am I funny? I make me laugh. Sometimes other people laugh too. Is that enough? Use conditional phrasing. I may be funny;

6.       I can juggle. Literally and metaphorically;

7.       I am smart. Obviously, otherwise the sorting hat would have put me in Hufflepuff; and

8.       I am a good writer. So why is this so difficult?

Your Preferences

And somehow even more difficult: What do I want in a man?


The perfect man, apparently.

Hot, cheesy, satisfying, reliable. Ok, so I’m describing takeout pizza. How different are they, really?

I paused to order an Italian sausage and mushroom thin crust pizza. I opened a bottle of red wine in the hopes that my roommate will help me drink it. Forgot that she hates red wine. Good thing I didn’t claim to have a very reliable memory in my blurb about me. Or did I? Bugger it.

Can I use the word “gregarious” to describe my ideal man? Do people know what that means? Would my ideal man know what that means? Not necessarily. But he’d look it up, I’m sure. Or he’d pretend to know, brass it out until years later when we’re going through our divorce papers and he looks me in the eye and tells me “I still don’t know what 'gregarious' means.” And I reply bitterly, “Why did we have to go to litigation over the unabridged Oxford English Dictionary hardcovers if you never freaking use them!?” My ever-tactful lawyer whispers something in my ear and I do some breathing exercises.

Is it rude to request that someone be literate? Or does using the word “gregarious” pretty much do that for me? It is not that I exclusively prefer bibliophiles. A guy whose idea of reading begins and ends with sports stats is fine with me, but comprehensible text messages are an absolute must.

So I think I have one basic requirement: literacy. High standards.

I started to notice a disturbing trend. All of my preferences seem to be based on attributes that I don’t want, rather than things that I do. Non-smoker, unmarried (“Why is that an option?” She asked naively), no kids, no hardcore gamers, no cokeheads. As though all of these non-things would coalesce together into one great guy.

What do I want? Well. I’ve decided.

“A little bit about who I’m looking for: someone who buys in, laughs lots, goes all-out, and who is kind. Most of the people in my life (and all of my favourites) have strong personalities, independent natures and a healthy appreciation of wit. My ideal partner is bright, active, gregarious and considerate.”

Sounds simple enough. Let’s see if the internet can find one. And whether I'll recognize him when the time comes.

Introduction: The Challenge

I go all-out for Lent. People who know me tend to roll their eyes when I say something like that. They are well aware. I go all-out for practically everything. Playing in a volleyball tournament? Team theme, costumes, props and mini cheesecakes for everyone! Haven’t seen the girls in a while? Plan a fake wedding so we can all be bridesmaids together, book a hall, invite dates and drink and dance the night away (obviously). Ok, so those are extreme examples, but they happened.

For me, Lent is about taking stock of the things in my life that I take for granted. I (temporarily) sacrifice something to determine whether I can live without it, how I really feel about it, and whether having it or denying it makes me a better person.

In previous years I’ve given up bread, meat, cheese, tea, pop, alcohol, popcorn, chocolate and sex. I’ve also given up more abstract concepts like swearing, the word “like,” wearing pants, and complaining about my boss. For every lapse or failure, I donate money to the charity of my friend Derrick’s choosing. I sometimes open myself up for suggestions (which is where the “no pants” restriction came from) and this year I was issued a singular challenge.

A brief note of explanation: I am a single girl in my early (if they even count as) thirties. I have been unabashedly, uncompromisingly, simply single for most of my life. I believe there are many different kinds of single; well, I am the kind that doesn’t date. I once signed up for online dating in a show of support for a friend, but I gave up without much ado. It is a safe sort of existence, and if you keep as busy as I do, it is rarely a lonely one. But then along comes Lent, and in my quest for a new challenge, a friend suggested that I give up being single.

The thing about Lent is that it is temporary. Any finite thing that ends before I do is by definition survivable. So even if it is difficult or ridiculous (which I’m betting this will be), I can do it. This year, Lent runs for 40 days and nights over a 45 day span from March 1 to Good Friday. During this time, I will go on 40 dates. I will also write about them, because at the very least I am going to get some good stories out of this adventure.

My first ground rule is that Netflix and hot chocolate with my roommate does not count as a date. Oddly, it is also my second and third rule. Rule number four is that repeats are ok. If one of these dates merits a second outing, I’m all for it. My fifth rule is that dinner with a friend counts as a date if I use that time to become better acquainted with them, and not just fall back on familiarity. I will probably make up a few more as I go.

In order to round up dates, I’ve sent messages out to my friends asking them for set-ups and started working on an online dating profile. I’ve still got a few weeks to sort all that out, schedule some dates, and mentally prepare to give up my benignly single life for Lent.

Wish me luck!


Editor's note: All names have been altered. Mostly just for the fun of it.