On dating

By day, I'm a mild-mannered web editor. By night, I'm a 25-year-old who's striving to live life to the fullest, make up for lost time and have a hell of a lot of fun. It means a lot of sleepless nights. A few steep bills for bars and cabs. Lots of teeny tiny dresses and towering heels. And, maybe, a little bit of a reputation for being fun, fearless, a wee bit reckless and even a tiny bit wild.

Obviously, my quest for new adventures has included a lot of new experiences over the past 10 months - a half-marathon, a ball hockey team, a tattoo, climbing the CN Tower, rock climbing and karaoke, to name a few. But my desire to embrace life - the beginnings, the endings and the messy bits, too - also involves romance, and, as a result, a lot of heart-related messy bits.

The question that I'm always asked is "When do you think you'll be ready to date/have a relationship again?" The dating part, I'm all over. The relationship is tougher. I've dipped my toe into dating, but remain fiercely protective of my current life - I'm not ready to make the compromises with my schedule, my living space and my "Why not?" approach to whatever plan is hatched. I figure eventually a guy will come along who will be able to keep up, and then making those compromises won't seem life a sacrifice. I want my next big love to be spectacular. Fireworks, baby.

While I'm not out actively seeking relationships, I enjoy exploring out the opportunities that do come my way. Meaning a string of largely unsuitable, but lovely, suitors. Many of whom remain a part of my life in decidedly not romantic ways. And each one of them has taught me something important, changed me, and left me feeling a little bit more ready for more. So, in a way of both explaining the romantic side of things - which I have, until now, largely glossed over here, despite it being a rather important part of my life, and perhaps, even thanking those fellows whose numbers, however briefly, topped my speed-texting list, a brief summary of my recent misadventures. (N.B. I give all of my gentleman callers nicknames. Partly because it's fun. Partly because the world is small, and there's a lot of overlap in social circles. Partly because otherwise, my friends would never keep track of them.)

1. My friends know him as many things, including "THE Boy" and by his place of employment. To me, he'll always be my "What if" guy. There was an undeniable attraction and connection, but we screwed it up. He came into my life while everything was falling apart. He saw more than his fair share of my crazy - in fact, he saw levels of crazy that I never even thought I was capable of. Had our timing been better, it could have been spectacular. And that's something I'll always regret. But he also taught me that I could still be made totally weak in the knees and that there are guys out there who can challenge all the different aspects of my personality - the news nerd, the sporty girl, the arts lover and the social butterfly, for starters. Out of all of my gentleman friends, he's the one who set the impossibly high bar for what I want in my life. One that not anyone who has followed has quite been able to meet. And how can I not be thankful for someone who showed me that such a special thing is not only possible, but essential?

2. Fake Boyfriend. Or FBF. Also known as my "Twittercrush" and by his place of employment. He was fun, and built a lot of my Ikea furniture. There was a definite spark between us, but neither of us was really in a place to commit to anything - thus the "fake." I was scared people would judge me for moving on, he was scared of seeming predatory, so we, to our detriment, kept our fling a secret. He was convinced I wasn't ready for a relationship - and, in retrospect, he was probably right, if a little harsh in vocalizing his diagnosis - and, quite frankly, I'm not sure if he was really all that into me. But we had a few fun months, and, in addition to his mad handyman skills, he was actually a really good friend to me and support in my time of transition. From him, I learned that I needed to improve my communication skills and explain what I wanted - or at least put into words that I didn't know. I'm still not good at that one. He challenged me. And reminded me that flirting is an awful lot of fun,

3. Old Dude. Kind of self-explanatory. And by old, we're talking almost daddy territory. The first time we went out, I didn't think it was really a date. I thought he was just being friendly. I went to a movie with him too, as a means of trying to be friends. He somehow managed to insult my weight, my home province, my attitude towards relationships, my social life and my personality throughout the two evenings we spent together. He's one of the few who's not still in my life, but he did teach me that not all guys deserve a second chance, and that life's too short to waste time with high-maintenance men who seem to think that dissing a girl will improve their chances with her.

4. A gentleman my friends know as "Mutual Friend." Because he has the potential to be a great friend, and a great boyfriend - for someone else. Our flirtation was brief. There was no spark. We wanted, and still want, different things. There was, however, a lot of signs of his being high maintenance - which is not what I need. His was a lesson in letting a guy down. Often. And that even when you think you're being clear with your intentions, sometimes people will still misinterpret them. And that as much as it sucks to be the mean one, it's even worse when, in your attempts to be nice, you leave the door open a crack and have to do it all over again.

5. The Hipster. The name he's known by to my friends is far too specific for the web. Another brief flirtation, he still pops in and out of my life from time to time. We always have fun, and fascinating conversations. He taught me that people with divergent priorities, personalities and interests can still have a connection -- and that guys won't always call when they say they will. And that when they don't, it's OK to hold it against them. Even if you're still friends.

6. Hockey Boy. Thus named for his interest in, you guessed it, hockey. Sharing a place of employment with a previous suitor, his moniker had to be a little less specific. I had a huge crush on him. We have a ton of shared interests and shared friends, and I got to know him very well over a serious text messaging routine, thanks to conflicting schedules. We had fun together, and had a wonderful habit of support and compliments. The basis for a wonderful friendship. When I finally confessed my crush, after an agonizingly long wait for a response, he told me he just didn't see me that way. Embarrassing. And sad. But we're all good now. And the experience taught me that it's better to go for it, and get an answer, than to wonder. Cause while it hurt, I don't regret for a second putting myself out there.

7. The Young Guy. Younger than I, but only by two years, geographically undesirable and a blast from my past. Way past. As in my teens. A wee crush, and a surprisingly lovely evening. He's been part of my life for years, in a totally platonic way, and we shared one late night of talks and hugs (totally PG, I swear!). And we talked about everything. From all the hairy details of my ruined relationships - he knew both my highschool boyfriend and my ex - to my life in Toronto and the many foibles of my family, even my grandmother's Alzheimer's and how my brother has changed since I moved away. It was comfortable and comforting. It was an ease of conversation, and a shared history, that I certainly miss in Toronto. And a wake-up call that someday, I want someone to be around long enough to not only know about my family and my secrets, but to be actively interested, empathetic and invested.

8. Part-Time Boyfriend. Or Trouble. He actually was around long enough that most of my friends started - gasp - using his real name. All along, I was warned that he wasn't a relationship guy. That he was commitment-phobic. As a fellow commitment-phobe, I figured I'd just see where it led. Over a couple months, we fell into a rather lovely routine of enjoying good conversation and each other's company. I had someone on my arm at parties, someone to talk to, and someone I could count on to fill in the "boyfriendy" role once or twice a week. And for the rest of the week, I could come and go as I pleased and maintain my fiercely independent lifestyle. Over time though, I got used to the routine. He was a pleasant habit, and I let other suitors slip. But he didn't. And he recently decided to go exclusive with someone who isn't me. Which, obviously, hurt. And, as with all recent wounds, still does a little. Because while I wasn't necessarily ready for full boyfriend mode, I had grown fond of him. We maybe weren't destined for a big love story, but we did have something. And I like to think that he wasn't lying when he said it was a tough decision to stop seeing me. He did teach me that I'm willing to let people into my life - he met my friends, I shared personal stories with him, and friends even knew I was seeing him, which are all massive steps for me - but that also, I'm not so good at casual. While I don't want someone to take care of me, or someone who makes me their number one priority, I do want someone who is at least interested enough in me to let their other suitors slip too. Cause I think I'm worth the undivided attention, even if it is only for a few hours a week over the course of a few months.

Other players have flitted in and out, a coffee here, a beer there. Guys like elevator boy and bar boy, who for various reasons just never became more than a passing memo in my Gmail calendar or a deleted contact on my phone. They don't make the list because they didn't win my affection - or disdain. They were just strangers, who remain strangers. 

If any of my nicknamed gents are reading this, well, you knew it was a possibility when you decided to date a writer! And, I do want to offer you all both my gratitude and my apologies. You each know why.

As for the next guy, and his shiny new nickname, we'll just have to see what life throws my way. Here's hoping for fireworks.