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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Candice is a 31-year-old writer and blogger who lives in Little Italy. “I do a lot of environmental volunteering, cycling the city, community activism, and partying too much on the weekends,” she says. (Candice is also “running a ‘Rob Ford Rides the City’ challenge to get the mayor to give cycling a try this June.”) She describes her style as “casual and bright” and herself as “really outgoing; excitable; often crossing the lines of appropriateness in jokes and conversation.” Her ideal partner is “intelligent, inventive, and light-hearted.” Ricardo is a 33-year-old post-doc at the University of Toronto who lives near Queen West. He describes himself as inquisitive—“I’m fascinated by how things work”—driven and attentive, and he likes to try out new things (for example: “trampoline dodgeball last week”). “I’m still discovering Toronto,” he says. “I like to randomly cycle around the city, discover its charms, and then Instagram with no shame.” He adds: “I find people with a clear drive quite attractive. Big plus if their output is palpable.” He prefers women who aren’t shy, are “probably either left or centre-left,” and smart.

Candice on Ricardo

“When Ricardo showed up, I noticed he was carrying a cycling bag, so I immediately knew that we would be able to connect on that. I’ve been hit while cycling three times, so it’s something that I care deeply about; I love to hear about other people’s experiences with cycling, and how they think they could be improved.

“Ricardo was cute, stylish, and outgoing. I wasn’t attracted to him, but he was a good-looking guy, so I was willing to give it a shot and see if an attraction could build. Personality can always win you over. He was a real gentleman and very conscientious, opening doors… I liked that Ricardo was the type of person who made sure that everyone around him was comfortable and felt respected. I’ve dated a few guys who would be oblivious to what’s going on around them, or how other people might be feeling.

“You could tell by Ricardo’s style that he paid attention to detail, too: everything was matching and he was really well put-together. We were both outgoing and not nervous, so that was nice. He listened to me when I was talking and he did make an effort to ask me questions, but in general he did most of the talking. It was interesting to hear about his ideas, and about some of the ethical issues around creepy things like Google glasses.

“When I told him about what I’m working on, like waste prevention, he immediately offered his opinion without asking for details to actually understand what it was that I was doing and trying to achieve. We disagreed about a few things; I think we’re both quite opinionated. If I wasn’t a bit hungover, we probably could have gotten into some serious debates, but I just wasn’t in the mood, and was hoping for something a bit lighter.”

CANDICE RATES THE DATE (OUT OF 10)

Overall: 6

Conversation: 7

Vibe: 7

Ricardo’s style: 10

Ricardo’s manners: 10

Ricardo’s shoes: 7

Ricardo on Candice

“Candice was sitting in the sun with her blonde hair shining proudly in the wind as I approached. Unfortunately, this was all I could muster from my first impression.

“We ended up at a table outside [in the] nice weather. I could finally allow myself to ask the question: Who do I have in front of me? We started with Rob Ford. I’m not sure why, actually. We then talked about the basics: who we are, where we come from, what drives us. We ended up going into detail about her non-profit, where she volunteers, my own work, and then a bit more about our families. We did have things in common, some of them fundamental to how we observe the world, and how we want things to move forward. We talked about the environment, and small versus big cities. Candice is a thoughtful person, worried about society, and trying to improve the world. She isn’t too idealistic, which is always a plus for someone in her position.

“All in all, the conversation flourished with ease, and it didn’t have the supposed awkwardness of a blind date. We ate, chatted, joked and enjoyed the afternoon until the excitement of meeting someone new faded away. It ended with the conversation slowly coming to an end; we had exhausted most of the obvious topics and then some, and there were moments of comfortable silence. I think we both saw a natural end to the date.”

RICARDO RATES THE DATE (OUT OF 10)

Overall: 7

Conversation: 7

Vibe: 8

Candice’s style: 6

Candice’s laugh: 7

Candice’s shoes: 4

Special thanks to Tori’s Bakeshop, 2188 Queen St. E., 647-350-6500. Follow @torisbakeshop and Like Facebook.com/TorisBakeshop.

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Alejandro is a 26-year-old financial consultant who lives at Yonge and Lawrence. He describes himself as “gregarious, worldly, and open-minded,” and says he “can always argue my way out of trouble.” He likes to explore the city, watch movies, and get drunk. Alejandro has been single for a few years and says he is looking for someone to “spend nights with, whether we’re on a couch, in a theatre, pub or concert hall, or in bed.” He met Kevin at a club.

Kevin came up to me while I was dancing alone and complimented me, saying that he thought I was a good dancer. He asked who I was with, and I said that I like to dance my stress away by myself. I liked Kevin’s big, full lips and his very forward approach. His friend came up and asked if I wanted to dance with their friends. There was good music and booze was flowing; we were dancing, grinding, and just having a blast. I decided that since it had been months since I got laid, and even though he’s not the Dave Franco–type I’m usually attracted to, I’d kiss Kevin on the dancefloor. Later, we went to the bathroom and he gave me a hand job.

Over the next week, we texted about our second date. Kevin wanted me to choose what we did, so I picked a movie I already had tickets for. After the screening, we went out for dinner and talked. I got a good vibe from him, and the conversation flowed naturally—it mostly centred on the trials and tribulations of being close with your family when you’re not fully out of the closet. We seemed fairly compatible and laughed a lot. After that, I invited Kevin back to my place for a nightcap, poured us some drinks, and then we went to the bedroom and started making out on the bed.

He closed his eyes while we were kissing, which was a turn-off for me. Then, he reached over and turned off my bedside lamp. I turned it on again a few seconds later. I’m an exhibitionist and a voyeur, so I don’t enjoy sex in the dark. I like to see what’s going on. But Kevin had the nerve to turn it right back off again. At that point, I just left it.

After lots of kissing, oral sex, and more handjobs, Kevin started talking about taking it further. I realized then that we might not be as compatible as I had previously thought: it turned out we were both tops. I had guessed incorrectly that he was a bottom. He literally begged me to be the bottom and, after about two minutes of his whining, I gave in. I was still horny.

We were on the bed in the total darkness, and he was fumbling with the condoms and lube, trying to penetrate me. It wasn’t really happening, and was more frustrating than exciting. I had to accept defeat and admitted that it just wasn’t working for me. A few minutes later, he got in a cab, and aside from a few text messages between us, I never saw him again.

Alejandro rates his date (out of 10): 6

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Jennifer is a 29-year-old receptionist and Toronto Rock cheerleader who lives at Bathurst and St. Clair. She describes herself as a “girly-girl” and says, “I like going to the movies and shopping—it sounds like I’m a 14-year-old girl—and I love travel, and have been to nine countries. I prefer checking out new cultures to going to an all-inclusive, though that would be fun as well.” Mitchell is a 26-year-old social-media manager who lives in the South Core. “I’m outgoing and spontaneous,” he says. “Once I was on a date and said, ‘Let’s drive to Niagara Falls and go gambling,’ and we jumped in a car and went.” He likes working out, being outside, and watching sports.

Jennifer on Mitchell

“When I arrived, I was happy to see I hadn’t been stood up for game seven of the Leafs playoff series. I was also pleasantly surprised that Mitchell is a good-looking guy. The date was definitely off to a good start. He was enthusiastic, friendly, and outgoing. I can usually tell within the first five minutes of meeting a guy if I’m going to want to spend more time with him or not, and I could see us hanging out.

“We discovered we have a mutual friend; we didn’t dwell on it for long, but I found it funny. People think Toronto is such a big city, but there’s always six degrees of separation. I was slightly worried going into this that he’d be someone I’ve dated before.

“We shared tapas. Mitchell always asked if I wanted to share the last item on the plate, instead of just helping himself, which was polite. I got him to check the score of the Leafs game a couple of times because there were no TVs in the restaurant but, other than that, he didn’t pull out his phone at all.

“When the bill came, we ended up splitting it. It was only $27. [Editor's note: The Hook-Up's restaurant partners waive the first $100 for our dates.] Usually, I feel that if a guy is interested, he’ll offer to pay for everything. I know that Mitchell is just starting a new job, so maybe it was a financial thing. That was the only slightly awkward part of the night. I am pretty sure I’ll hear from him again.”

JENNIFER RATES HER DATE

Overall: 8

Conversation: 9

Vibe: 8

Mitchell’s manners: 9

Mitchell’s laugh: 8

Mitchell’s shoes: 6

Mitchell on Jennifer

“When I met Jennifer, I was relieved, because I thought she might cancel since the Leafs were playing in game seven. Right off the bat, we were joking about being set up, and whether one of us would cancel because of the game. I thought she was put together nicely, and was very attractive.

“As we moved inside, the conversation continued to the point where we had to make an effort to stop talking so that we could order drinks. We also chose a bunch of different dishes to try.

“Jennifer has traveled a fair amount, which I really liked because traveling is a passion for me, just like being active. There were some points where I thought the conversation trailed off a bit, but Jennifer did a good job picking it up. It was a very easy, low-pressure date. I didn’t mind the fact she was a bit older than me, but I think she might be looking for someone closer to her own age. We could be at two different stages in our lives.

“The bill came and we kept on chatting, and, when we went our separate ways, we ended up on the same streetcar. We continued to check our phones to see if there was any update on the Leafs game, and before Jennifer’s stop I asked her for her number. Is there a spark? I’m not too sure, but I am open to seeing her again and seeing where it goes.”

MITCHELL RATES THE DATE

Overall: 8

Conversation: 8

Vibe: 8

Jennifer’s smile: 9

Jennifer’s sense of adventure: 7

Jennifer’s wine choice: 9

Special thanks to Kultura, 169 King St. E., 416-363-9000. Follow @Kultura_Toronto and Like Facebook.com/kulturatoronto.

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