Lessons Learned Over 40 Dates

Beginning Is the Hardest Part

Yup.

As with anything massive or bold or different, the hardest part is that first tentative step. After that, there is momentum to take you forward, keep you going. The first message to a guy online, the first text to set up a blind date, that’s where the real challenge lies. After that, you just keep rolling until Good Friday dawns like a glorious curtain coming down. Show’s over and I survived.

Just Keep Swimming

The last paragraph made it sound like it was all sunshine and rainbows and playful kittens. It was not. There were plenty of storm clouds and blizzards and evil fully-grown cats who do not like me. But, to further my earlier point, the momentum built up by taking that first crazy plunge helped a lot.

Not remotely my goal

Other things helped too.

Helpful Thing Number 1.          Deadlines help. And a finish line to strive toward. Because a girl’s gotta have goals.

Helpful Thing Number 2.          My super amazing friends were an incredible support system and a great source of dates. You know who you are, and I love you.

Helpful Thing Number 3.          A big, old-fashioned day timer and coloured pens to schedule all my dates (in purple to make it fun), volleyball games (in green because green is my favourite), and all of my other commitments (in blue and black, mostly).

Not a goal, either

Helpful Thing Number 4.          My super-human stubbornness. So very helpful.   

Helpful Thing Number 5.          When motivation wanes, it helps to have an audience. I grew up playing team sports and my parents did their best to instill team values in me, and I think it worked. When things get tough, it helps to have a team that I can’t let down. That has been you, so thank you for that.

Between the momentum and those helpful things, I made it through just fine. One date at a time. I actually met my goal a few days early and I even managed to have some fun along the way. So it all worked out. 

Personal Grooming

Ok, so this one seems obvious to most of you. Not to me.

I’m a tomboy, I like to sleep in and mostly I don’t give a damn about makeup and hair and the accoutrements of pretty. My philosophy is that I look the way I look, for better or for worse. When I do get gussied up, you know it’s for a special occasion and you’d bloody-well better be impressed.

But in my foray into dating, I discovered that feeling confident is actually better for calming nerves than a bracing shot of whiskey (especially if you’re driving). And if a bit of makeup, or a great haircut (Thanks, Liz!) will give me that little shot of confidence that I need to sit down and introduce myself to a total stranger, then so be it. Groom away.

I will allow it. This time.

Boys Are People Too

"Oh my god! Great shield!"
"I know, right? You don't think
it's too much?"
"Dude, it totally suits you."

One of the things that I tried to do was to maintain a level of respect and discretion through all of this nonsense. I wanted to treat all of my dates the way that I would like to be treated. It is weird that I had to keep reminding myself that these dates were real, living people with thoughts and feelings. Sometimes you forget. Especially online. It’s easy to write people off when they’re just a profile picture and a disembodied line of text on a computer screen. I think that depersonalizing people while looking for somebody to date is a very slippery slope and can result in some pretty ugly behaviour. I’m happy to say that I didn’t get many “Fuck you ugly bitch!” responses when talking to guys online (and zero in person, which was a relief). But I was also very careful not to demean or disparage anybody. Ok, maybe Geoffrey (the guy I am pretty certain is a serial killer), but seriously, that dude was legit frightening, and I didn’t use his real name, though I’ve been told that my sketch was pretty spot-on.

Also, with the exception of the speed dating guys, everyone knew about the 40 Date Challenge going in. I’m pretty sure they all knew that I have been blogging about it (and them). Oddly, none of them expressed an interest in reading it. I think I would be overcome by curiosity. But maybe that’s just me. Or maybe boys aren’t really people after all? No. They’re people. Be nice.

Advice



Simply put, I can never get too much advice. No such thing. My girl friends sharing horror stories of dates gone embarrassingly or morbidly or hilariously wrong and offering those up in the form of advice made for some of the best stories I’ve ever heard. I got to commiserate, cackle and learn. It was one of the highlights of the 40 date adventure, for sure.

I'm that girl.



Other, less amusing advice has come my way as well, and it was all wonderful. Friends offering me guidance on how to cope with rejection, how to navigate the scary world of online dating (because apparently I am a total luddite), how to fend off dick picks, where to go on dates, what to talk about, what not to talk about. Most of the advice came with a story, which made it even better.

Hey, I think we're going the
right way, Stevie! Stevie?

A friend asked me for advice about dating, and I joked that it would be like Ray Charles leading Stevie Wonder across the street. But even if it ends in disaster, it’s nice to have another clueless friend to laugh with and remind one another that we’re not alone. So I’ve been doing my best to offer advice in return and help others as I’ve been helped.

Admittedly, I did not, will not, cannot follow all of the advice I receive. But it is great to hear about, great to share. “Advice is a form of nostalgia. Dispensing it is a way of fishing the past from the disposal, wiping it off, painting over the ugly parts and recycling it for more than it’s worth.” (Mary Schmich)

Routine Chaos

So long as I can tell myself it’s a routine, I can handle utter chaos.

So long as I write them all down in my calendar, it’s totally doable to take on 40 dates, 56 volleyball games, two tournaments, three road trips, blogging (almost) daily, regularly scheduled brunches and tea dates and a 9-5 job. Sure it hectic, but at least it was scheduled.

Needing Someone

There is an old saying that makes me laugh. “Men are like blenders: you need one, but you’re not sure why.”

I am a fairly independent person. I’ve lived alone, travelled alone, I like going to movies alone, I’m not big on public displays of affection and (though I like plenty of sentimental romantic comedies) I’ve never been into sappy love crap. I hate Valentine’s Day on principle. I am basically, peaceably, utterly okay on my own. So long as I have hot chocolate and toast.

But everything and nearly everyone tells me that I need someone. I think that lesson is one of the reasons my friend challenged me to this.

I am not sure I learned it. My independent streak is still totally intact. And I am not sure that I really need someone else in my life to make it complete. But I am a little more open to the possibility that having someone else around wouldn’t be the worst thing ever. So there’s that. Baby steps.

Talking to Strangers

One of the cool things about the 40 Date Challenge is that I learned how to talk to strangers. It helped that my first date was with Constantine, and we pretty much talked for two and a half hours without pause. Over the course of Lent I rarely had to sit in awkward silence. Even with Geoffrey  I wasn’t grasping at straws conversationally. And the fact that I was deeply uncomfortable had more to do with his creepy demeanor and bizarre gambits than any defect in conversation.

Not that there isn’t room for improvement here. I think, especially with Constantine, that I could have done better. We talked about how cultures that do not have a word for the colour blue also cannot distinguish it on a colour scale until they develop a word for it (How freaking cool is that!?). But we never talked about our expectations, or what exactly we wanted and needed from one another. He sort of stopped texting me, stopped reaching out, and I had no idea of whether that meant anything or not. I think that was probably a failure of communication.

A Recipe for Illness

Exhaustion looks
kinda like this

I managed to (sort of) keep it together until Lent ended, but stress takes its toll. I’m not just being dramatic here, dating is stressful. Even the good bits are an energy drain, and planning it all, struggling to keep my life on track in the meantime and trying give each date the fullest of my attention (and not always succeeding) may be the surest test of my endurance that I’ve ever managed.

I’m paying that toll now with a crazy head cold and a thorough inability to focus. Trying to sort through the labyrinthian mire of my life as I left it is not made much easier by having a head full of ooze.

Reason suggests, and science confirms that stress weakens your immune system. So my gung-ho, all-in, no-holds-barred survival mode kept me going for 40 dates, but the moment it was over, my body pretty much shut down. I drove back home to see my family for Easter and my pathetic defenses were easily overcome by the head cold that had been making its rounds amongst my kin. And a vicious little bastard he is, too.

I’ve been chugging orange juice, popping decongestants, and trying to rest while getting my life back on track. Just might take a little longer to achieve normalcy than I had hoped.

No Going Back

Oh yeah, also, normalcy might not happen...Because I’m not certain that I’m single anymore. It's that tricky difference between plans and reality rearing its ugly head once again.

Plans

Reality?
Not sure