Contest closes Monday June 24, 2013 at 2:00 PM.

Caleb is a 29-year-old chef who lives in Bloorcourt Village. He describes himself as friendly, shy, and funny, and enjoys biking, skateboarding, and trying new restaurants. Caleb says, “I work a lot of hours at night, which makes it hard to find normal dates.” He met Ginnifer on OkCupid.

I had just gotten out of a relationship and was in rebound mode when I found Ginnifer on OkCupid. I liked her laidback attitude, and she also looked really cute in her pictures. We texted a few times but nothing happened. I figured she had just lost interest or started seeing someone else. A few weeks later, I posted a “Let’s meet for drinks” broadcast, which shows where you’ll be and what time you want to meet to see if any females might be interested in shooting some pool and drinking beer. Ginnifer replied to it.

We met up at a dive bar near my place. Ginnifer had pink hair by then and looked like a rave baby. I said hello, and told her to watch out for the crazy lady who hangs out at the bar—she seemed extra crazy that night. I was really just making conversation, but Ginnifer said, “Why? She’s just doing her thing.” The awkward pause lasted about 30 seconds. I’m a positive person, so I just changed the subject.

The vibe was bad, and the conversation was lacking. When I reminded her that we had texted before and asked why she stopped replying, she told me that she was using OkCupid a lot, and that she goes on a lot of dates with different guys, which I thought was weird to admit. It was clear that she had a totally different personality than mine, but I still thought we could have fun. I ordered a pitcher of beer and we played a few games of pool. The beer helped things along a bit.

Then Ginnifer went to the bathroom, and a minute later, I got a text from her that read, “I’m on the worst OkCupid date. It’s making me miss you. Let’s hang out soon.” She had obviously meant to send the text to someone else. When she came back from the bathroom, I played it cool and tried to act like I didn’t just get a brick in the face. I asked her if she was having a good time, or if we should just end the date. For some reason, said she wanted to stay, but added that it was because she “had nothing better to do.”

I pulled out my phone, showed her the text, and said, “What the fuck is this?” I asked if she had a boyfriend or something. She was silent for a few moments, and then said, “I meet a lot of guys through OkCupid, just to hang out and meet people.” It was a strange response—with no apology, even though I was clearly pissed. I took a shot of tequila, got my jacket, and left.

Caleb rates his date (out of 10): 2

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Contest closes Thursday, June 20, 2013 at 1:00pm ET.

Nadine is a 26-year-old public-relations consultant who lives near Queen West. She describes herself as “happy but sassy” and says, “my number-one favourite thing to do is cook.” Nadine also likes “chilling on the couch watching TV, going to the movies, going out for dinner, or late-night partying: I’m down for whatever as long as I’m surrounded by friends.” Nadine is looking for someone who is “successful in life, independent, and stylish.” Jamie is a 27-year-old financial analyst who lives near King West. (Jamie was featured in The Grid’s Dating Diaries special issue last February.) He describes himself as “honest—I have no time for bullshit” and a good cook who likes to “crack terrible jokes to make my friends laugh.” Jamie likes to be active, travel, and “go to the pub with friends.” Jamie’s dealbreaker is a woman “who describes herself as ‘shy’ or ‘quiet.’”

Nadine on Jamie

“My first impression of him was good, because he was open to the idea of the date and engaged in conversation right away, and made me laugh. He mentioned that he had done [a blind date through The Grid] once before, and that was a bit of a turn-off, because nobody should start a date by talking about someone else they went on a date with, especially if it didn’t work out.

“Throughout the date, Jamie was a little too touchy, and talking too close, but maybe that’s just who he is. I was a little uncomfortable with that, considering I had just met him that night. I’m not a prude; it was just uncomfortable. This may have also been because I wasn’t attracted to him. He’s good-looking and clean-cut, but just not my type. I’m sure some girls would really like him, though.

“I found that Jamie wasn’t very passionate about anything other than drinking; he made a bunch of jokes about getting drunk. I just got a bit of an immature vibe. Don’t get me wrong, I love to drink! He didn’t mention any hobbies; he breezed over his job and he didn’t really mention his family. Oh, and he held on to the popcorn all night, which made it awkward to grab some, as it was sitting in his crotch.

“I think that he was super nice, laughed at my jokes, and tried really hard but, in the end, I think he was trying a little too hard. At the end of the date, we hugged and he said, ‘So, do you want to go on a real date?’—which I said ‘yes’ to.”

NADINE RATES THE DATE (OUT OF 10)

Overall: 6

Conversation: 8

Vibe: 6

Jamie’s style: 7

Jamie’s manners: 6

Jamie’s hair: 7

Jamie on Nadine

“It was really hot and humid the day of the date, so I arrived glistening with sweat. Great first impression by me! At first glance, my thoughts about Nadine were that she was cute and had a nice body. She was wearing an animal-print jacket. I couldn’t decide if I liked it or hated it, but what do I know, I’m a guy. She was easy to make small talk with and seemed pretty chill—definitely someone I’d hang out with. We chatted about how naive I am with regards to musicals and ’60s movies, and how she’s a Justin Timberlake super-fan and possible stalker. It was too bad we weren’t at karaoke.

“The conversation and wine were just starting to flow when we had to go in for the movie, which was a buzz-kill. At intermission, I was getting tired and fading out, and made some stupid comment about how the [West Side Story] actors were such great dancers and in damn good shape, but that’s what happens when I don’t eat and just drink wine. Or, maybe I just find dance-fighting amusing!

“We exchanged numbers before she got in a cab. She’s a cute girl. I’d give it another date where we could talk and hang out more, but I wouldn’t be crushed if it didn’t happen.”
JAMIE RATES THE DATE (OUT OF 10)

Overall: 6

Conversation: 5

Vibe: 2

Nadine’s manners: 9

Nadine’s sense of humour: 8

Nadine’s hair: 8

Special thanks to the Toronto Symphony Orchestra (212 King St. West, 6th floor, 416-598-3375) and Roy Thomson Hall (60 Simcoe St., 416-593-4828). Follow @TorontoSymphony and Like Facebook.com/torontosymphonyorchestra.

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Colleen is a 25-year-old who works in shipping and receiving and lives in the Entertainment District. She describes her style as “skid meets a Dov Charney sex fantasy,” and says that she “persistently offers too much information” and enjoys getting drunk and eating pastries. Colleen is looking for someone who can handle her. She met Luke on OkCupid.

I liked Luke immediately because he seemed crazy. His profile had all these pictures of him doing weird stuff, and he sent me pre-date sexts and pictures of himself wearing a loincloth. He seemed perfect for me. Based on his extreme physical attractiveness, I knew seeing him would be a long shot, but he responded to my initial message of “LET’S FUCK” appropriately with, “A bit forward, but sure.” He asked me out, but I already had a date that night with a guy I’d been blowing off. I double-booked anyway, and told Luke I’d meet him later on.

I met the first guy at a bar. He had seemed like a rugged, outdoorsy type online—which I’m really attracted to—but he was actually balding and creepy in real life. Hanging out with him was boring, so I invited some friends to come. When we all left at the date’s end, I made out with the guy on the subway platform and promised to see him again the next night. Then I texted Luke to meet me at my place. On the way home, I chugged some Gatorade and ate a million saltines, hoping to sober up. At that point in my life, I was inviting strangers into my apartment way too much.

Luke was perfect in every way; we had an immediate connection. When I opened the door, this crazy, beautiful guy with a huge beard and holey clothes barged past me, dumping a six-pack on my counter in the process. He walked into my bedroom, where he went through my closet looking at my clothes. He chose a dress, took off all his clothes, and put it on. We spent the night drinking, trying on my dresses, dancing around naked, making out, and sleeping. The first guy of the night had described himself as a much more attractive person than he really was, but Luke described his penis as a “baby dick.” I loved the honesty—it was a major turn-on.

The next day, Luke and I spent hours driving around the city, going to thrift stores, and playing weird made-up games. Unfortunately, I had promised to meet the guy from the night before, which I remembered at the last minute, so I made up an excuse about a dinner party to get Luke to drive me to the guy’s house. As I was ferociously making out with Luke in the car outside of the other guy’s house, one of my friend’s little brothers walked by and saw me and yelled, “Colleen?!” I got out of the car to say hi, as Luke drove away honking. It was the best date I’d ever been on. That night, I begged the other guy to make me dinner, since I hadn’t eaten all day with Luke. Then I made the mistake of sleeping over. He farted all night in bed.

Colleen rates her date (out of 10): 10

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Victoria is a 22-year-old administrator who lives in the Annex. “I like to walk around Toronto with friends, read novels in coffee shops, and tan and swim at Christie Pits in the summer,” she says. “I can usually make a connection with people, and make them feel comfortable.” Her ideal guy would be “friendly, accommodating, and well-liked, but decisive and not afraid to take charge.” Matthew is a 23-year-old graphic artist who lives in Brockton Village. “I’m a pretty big beer nerd—I collect and research beer like most people do records,” he says, before adding, “I love talking to people, helping them with their issues, and just being a good pal in general. I’m super-ambitious and optimistic, but also humble and realistic. It’s good to have my shit together so well at such a young age, but I don’t really gloat about it.”

Victoria on Matthew

“Matt came around a corner and introduced himself. I was pleasantly surprised: I liked his shirt, and I thought he was cute. If I saw him in a bar or something, I might talk to him. He was more confident in the situation than I was. He went in for a hug, which is not my usual greeting of choice, but I went with it. I admired his brave fashion choice of bright red Keds and no socks. Nothing turns a girl off like a pair of tube socks.

“The exhibit was a good idea for a first date; it’s kind of interactive. We made some small talk and had some beer. I liked that Matt was from the States and had adopted Toronto so readily. I felt like I was being awkward because I was tired from work and had managed to get my gum stuck to my fingers and was trying to subtly release it.

Matt told me about his interest in music, and how he is active in bands in the city. Of course. I rarely meet a guy my age who has never been in a band. We have a similar laid-back view of life and things that are worth worrying about. He didn’t ask me many questions about myself, though, and I would have to volunteer information at random.

“Matt asked for my contact info, but he told me to text him sometime, which is a possibility, [but] I thought that was fishy. Also, he had forgotten my name. No hard feelings on that, though. I’m willing to see where it could go. Plus, I want to try out this brewery he was telling me about.”

VICTORIA RATES THE DATE (OUT OF 10)

Overall: 7

Conversation: 7

Matthew’s style: 7

Matthew’s manners: 9

Matthew’s hair: 8

Matthew’s scent: 8

Matthew on Victoria

“My first impression of Vicky was good, although I think I took her a little off-guard by saying, ‘Hi’ before we were introduced. I’d say the first things that stood out to me were her nice eyes and red hair, since I kind of have a thing for both of those.

“Initially, she was a tad nervous, but she definitely seemed more relaxed as we talked more. The vibe in the gallery was pretty cool. We talked about a lot of different stuff like movies, TV, music, hobbies, traveling, careers… I thought the conversation flowed pretty nicely. She seemed pretty curious about the stuff I’d been up to, which was cool. Something that was endearing was that I have this goofy philosophy called ‘living well’ that I told her about, and she’d occasionally bring it up for laughs. I also got the impression she’s pretty close with her family, which is always a really positive thing.

“All in all, I wouldn’t say she’s totally my type. I really like girls who are goofier and more quick-witted, and not afraid to poke fun at me in a flirty way or just flirt a little bit in general, but Vicky seemed a little reserved. I’m a pretty outgoing dude, and I like it when someone reciprocates well. That, and I like it when my date has or has had really weird, cool, or intriguing hobbies or vocations, or other things she’s into. You know, something not super ‘out there,’ but something that sparks a bit of intrigue and is a quirky addition to her personality. But, it would be cool to see her again.”

MATTHEW RATES THE DATE (OUT OF 10)

Overall: 7

Conversation: 7

Vibe: 7

Victoria’s manners: 9

Victoria’s sense of humour: 8

Victoria’s hair: 8

Special thanks to the Norman Wong x Arts & Crafts exhibit, part of the Scotiabank CONTACT Photography Festival. Wednesday to Friday, noon-7 p.m., Saturday, noon to 6 p.m., until June 15 at the A&C Pop-Up (1093 Queen St. W., Unit 2).

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Dariya is a 32-year-old television producer who lives in Cabbagetown. She says, “My style is ‘smart professional’ with punches of artsy hippie,” and describes herself as “confident, creative, intelligent, boisterous, and sometimes too silly.” Dariya likes to hang out with her dog, go to the theatre, try new restaurants, and read. She has been single for two years, dating on and off.

I’m looking for a guy who is smart, but not full of himself, flexible enough to mix with my artsy and academic friends, good-natured, and well-read. I had been online for a few weeks when I met Mark on OkCupid. In both his profile and subsequent communication, he seemed to be really smart, sarcastic, and thoughtful. It seemed like he’d be a good match for me. We agreed to meet up, and I suggested a pub loud enough to provide a good exit strategy, if the need arose.

When I walked in, I was surprised that Mark was a lot shorter than his profile indicated, and looked much older than he said he was. Nevertheless, I sat down and we started chatting. He was more acerbic in real life than online, but I sensed that it was coming from nervousness; he was quite fidgety. Our conversation moved beyond the usual small talk right away. As we bounced from books to the Eurozone to our families, he started to loosen up. About three hours later, having had a few drinks, I was starting to find him rather cute and clever. A band started playing in the pub, so we decided to head to another bar where we could continue talking.

That’s when things got weird: As soon as we sat down at the second bar, Mark reached into his jacket pocket and pulled out a folded-up piece of paper and a pencil. We ordered our cocktails, then he ceremoniously unfolded the paper, smoothed it out on the table, and cleared his throat. Mark told me that he had prepared 30 questions for me. The first question asked whether or not I could do any impressions. I said no, and he made fun of me and said that everyone could do an impression. He made some notes on the piece of paper.

After a few more questions, I asked him about the notes that he was making; he said that he was scoring me, and that, so far, I wasn’t doing very well. By question 15 or 16, I was starting to lose my mind. Apparently, my choice of Arthur Russell as “the dead ’70s musician I would most want to have dinner with” was a terrible answer. When the waiter came by to see if we wanted more drinks, I said, “No!” The bill came and I made no move to split the tab as I normally would have. Mark walked me out of the bar and then, unbelievably, asked me if I wanted to go on a second date. I just waved goodbye and walked away, shaking my head.

Dariya rates her date (out of 10): 4

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Stefanie is a 34-year-old talent agent who lives at Church and Wellesley. She likes cooking and going to concerts—“I’m a talent agent that specializes in live music, and it’s my passion, so even if I spend all day listening to music and thinking about music, I still like to go out and hear live music, even if it’s not work-related.” She adds, “I’m the person who gets the call when someone needs to put together an outfit for a special occasion as much as I’m the person who gets the call when someone needs to be talked through a complete meltdown.” Her ideal partner is “as bomb-proof as I am. I have enough drama with my friends and work.” Kevin is a 39-year-old former Parkdale resident who has “temporarily moved back to Hamilton” to fix up a rental property. He is the president and CEO of The Idea People, owns and teaches at the Impatient Theatre Co., and is a photographer. Kevin hangs out with his dog, does improv, watches a lot of TV and movies, and likes to travel. He says, “I have had a tendency to put the interests of others before my own, but I’m now focussing a lot on my own personal development.” Kevin is into women who are “intelligent, vibrant, social, confident and passionate.”

Stefanie on Kevin

“My first impression was that of mild confusion. I walked into the B.A.T.L. venue, and nobody really stepped up to introduce themselves. When I figured out who my date was, I thought he was dressed well and had a good haircut and good shoes, but he seemed to be a little shy. I felt like I had to take charge of the situation. He would have made a much better first impression if he had just introduced himself right off the bat.

“I really wasn’t attracted to him. I’m generally attracted to very confident men with strong personalities to match my own, and I just didn’t get that confidence from him. It’s a drag for a girl to have to walk into a first-date situation and feel like she immediately has to take charge. Maybe that’s just a function of my personality and something that I tend to do naturally, but I’ve been around enough naturally confident men to know the difference between a man who just takes charge, and a man who needs a little guidance.

“The [axe-throwing] lesson was pretty hilarious. I’ve been to B.A.T.L. before, so I knew the rudiments, but I’ve never been that good, so getting an actual lesson was great. Kevin picked it all up pretty quickly and eventually beat me. I’m hyper-competitive and tried to be a gracious loser, but it wasn’t easy. Because Matt [Wilson, the instructor] was there, it alleviated a lot of the first-date awkwardness; throwing axes around is a great way to ‘break the ice,’ as it were. Once Kevin’s initial shyness wore off, we had a lot of fun goofing off with the axes and hamming it up. I spent a lot of time swearing at him and calling him names when he hit a bull’s eye. I liked his sense of humour, and we both laughed really easily.

“Otherwise, we mostly talked about work. Kevin’s a photographer and showed me some of his stuff, which I thought was really good. I told him I work with bands and he expressed some interest in shooting them, so it got very work-y and not very date-y. He gave me his card at the end of the date, but it wasn’t in a ‘let’s get together again’ kind of way.”

STEFANIE RATES THE DATE (OUT OF 10)

Overall: 6

Conversation: 5

Vibe: 5

Kevin’s manners: 7

Kevin’s sense of humour: 9

Kevin’s hair: 10

Kevin on Stefanie

“When Stefanie walked in, I knew instantly that we would have a good time. She has a great attitude, and she’s confident and approachable. She had been there with a friend before and had contemplated joining the league, so I immediately felt at a disadvantage and knew my manliness would be tested. Needless to say, it survived the date.

“Stefanie’s not the kind of woman I would typically date. I wouldn’t ask her out on a romantic date, and I don’t think she’d be interested, either. I would, however, happily set her up with any of my single friends. She’s a very lively, spicy woman. We got along really well.

“We began with some instruction, and after a number of warm-up throws, Stefanie and I had a standard match, which I won. Stefanie was in her head, throwing bricks, which we were told is common as soon as competition enters the picture, proving that the competitive setting was an issue; Stefanie threw an amazing dead-on bull’s eye on her first shot after the match. We graduated from hatchets and had a couple of throws with a full-sized axe; it was exhilarating. There was a lot of laughing and joking and friendly ball-busting.

“Stefanie is an outwardly confident, ambitious person who absolutely loves what she does. You can hear the passion in her voice when she talks about music. I think I’m looking for someone a little more settled, a little more relaxed, and a little less brash. I wouldn’t want her to change a thing because she’s perfect for someone, just not for me. After the date, we walked out and parted ways.”

KEVIN RATES THE DATE (OUT OF 10)

Overall: 8

Conversation: 9

Vibe: 8

Stefanie’s style: 9

Stefanie’s hair: 8

Stefanie’s axe-throwing: 6

Special thanks to the Backyard Axe Throwing League, 213 Sterling Rd. Email league@batl.ca or events@batl.ca. Join the B.A.T.L. Facebook group and follow @BATLToronto.

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Find me: Facebook.com/jamal.r.prentice. | Neighbourhood: Applewood Hills, Mississauga. |

Basics: Student, volunteer, gamer. | Who pays on a first date?: The gentleman does. |

What keeps you up at night?: Will I ever completely love myself, or will I just keep trying to?

Having trouble reading the text below? Click here for a close-up look.

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Alannah is a 23-year-old marketing assistant who lives in the Entertainment District. She says her friends would describe her as “kooky, animated, and strange—in a good way.” In her spare time, Alannah bakes, scouts new places for fish and chips, watches films, takes improv classes, and plays Scrabble. She met Tom online.

Tom messaged me, but he seemed like a self-indulgent hipster brat, and I immediately didn’t like him. I had my 100-point checklist of required qualities, most of which Tom was missing. He seemed cute, though, so I agreed to go out with him. He asked me to meet at the corner of Bloor and Avenue, in front of the church. He turned out to be stunningly handsome, tall, blue-eyed, just out of a long-term relationship, and a “writer.” But I come from a hard-working, practical background, and I didn’t quite understand his lifestyle.

The date started at Hemingway’s, where he ordered pretentious beer and kept leaving to smoke. Right away, we were exchanging barbs. The conversation was aggressive and we kept one-upping each other. We both got stupidly drunk. Somehow, things felt natural and in-sync, even though, technically, the date was a disaster. Once our defence mechanisms gave way, we had a conversation that made us realize we actually had the same sense of humour and worldview.

Drunk and intrigued, I suggested we go somewhere fun. We made our way over to Woody’s, which was my idea, because where’s a girl to go on a date other than a gay bar? We ordered another pitcher and a guy hit on Tom—I thought it was cute, and he took it in stride. After an ungodly amount of beer that would make the average lout cringe, we headed over to a park where we talked some more. A smile here, a smile there, and we kissed. It was electric. We kept making out with him holding me, both of us looking up at the stars. Maybe it was the beer or maybe it was magic, but I felt smitten with him.

Eventually, we made our way to Pizza Pizza, and he ordered me a big box of fries. We perched at Yonge-Dundas Square, and he laughed at my appetite as I ate it all. When he asked if I wanted to go back to his place, I said yes. We hailed a cab and were on our way, but a block into the ride, I suddenly decided I didn’t want to go. We stopped the cab. Tom walked me to the subway and rode with me to my stop. I stole his blazer before I left. Despite the greasy food, we were both still drunk.

The next morning, I woke up with the worst hangover of my life. Around noon, Tom sent me an email asking, if he hadn’t blown it with me already, whether I would consider seeing him again. I said yes, and our next date was spent eating cupcakes. We’re still together. He is the exact opposite of me, but he’s the perfect opposite. I blame our awful—but wonderful—first date on the completely crazy, hopeless, illogical, life-changing feeling of love.

Alannah rates her date (out of 10): 10

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