KY & She Does The City asked women: What’s the best date you’ve ever been on? After trolling through tons of submissions, we found a winner, and a few other dates so good we couldn’t help but share with you. Read on to hear about dates that run the gamut from the perfect night out, the perfect night in, the perfect night naked, and the perfect proposal. 

The Winner! Tania’s Chivalrous 24-hour Date  
How we connected?  Well, Facebook of course!  He recently looked me up, but we actually met in person 6 years ago through a mutual friend.  I still remember the initial sparks that flew between us back then (Modest Mouse concert @ the Kool Haus provided the perfect backdrop). But afterwards we went our separate ways, as you do…

After a phone chat 5 weeks ago to catch-up, and then an incredible afternoon coffee/jaunt down to the beach on the first warm spring day of the year (even our “pre-date” date was awesome) we arranged to go out that Friday night.

In the afternoon he texted to ask what my favourite colours were. Blues and purples and greens of course! When I opened my door upon his (very punctual!) arrival for our date, he had a massive bouquet of Lilies, Irish Bells and Birds of Paradise, as well as a cheeky grin.  He loves flowers! (I was certain a flower-loving man was an anomaly, but two orchids and several daffodils later, I’ve never had so many in my apartment!) 
 
He made a reservation at the CN Tower restaurant. I’d never been up there before! Not once in my 13 years in the city.  Perfect seating, gorgeous meal, amazing conversation…and he even snuck over to my side of the booth for a while to be closer (swoon).  Lots of giggling. Lots of butterflies in the tummy. Shared dessert.  Yum. 
 
This perfect date continued for over 24 hours!  I’ve never laughed so much, had so much silly fun or felt so comfortable with someone so quickly.  The day after the CN tower, we got smoothies at Fresh on Bloor and hit-up the Zoo, making fun of the adorable animals and witnessing all sorts of spritely spring behaviour, including a frisky Lion makin’ moves on his Lioness. 
 
Unfortunately, I fell ill with a cold that weekend of our first date during the spring thaw. So after the zoo it was home to sleep off all the excitement The next morning, of course, I was greeted by my (now) boyfriend with a care package, packed to the brim with neo citron, lozenges, soup and other sore-throat-friendly snacks, a selection of teas…the list goes on.  But I must not forget the soft fuzzy blanket he brought “to keep (me) extra cozy and warm!” As well as one of the afore-mentioned orchids. 
 
What else can I say? This gorgeous fellow is the goods.  He even holds doors open and walks near the road when we are side-by-side on sidewalks.  Chivalry is not dead and I am a believer. 

Runner Up: Meredith’s Ice Cream Date 
I think I should clarify first how I met this guy. I was at a ball. Yep, in Abu Dhabi, we still have balls. Anyway, this charming Dutch man approached me and said, “You look like a girl who could use some ice cream.” Well, I thought that was pretty funny and for the rest of the night I kept ordering ice cream floats from the bartender. (He had no clue what I was talking about) and we joked about the ice cream. Later in the night my hot Dutch guy said, “I’ll be right back.” When he returned he had a bag full of Baskin and Robbins ice cream for me. Cute, huh?    

But that wasn’t the best date. This is an example of the type of dates this guy planned. There were many more that rocked as well! On our first date he picked me up. When he arrived he had also brought ice cream. SO FUNNY!  He took me to the Shangri La hotel (a gorgeous hotel in Abu Dhabi) and we went to dinner at the Vietnamese restaurant.(SUPER nice) He ordered some lovely wine and then we ordered a bunch of different things and started chatting. The restaurant is gorgeous. The wine was good and he was super hot. After dinner he asked me if I wanted another drink.

“OF COURSE,” I said. 

He then got the concierge to bring around a golf cart that took us to our next destination. It was a bar called Pearls and Caviar. It overlooks the Gulf and there was a nighttime view of the Mosque. We sat there well into the night drinking cocktails and just making that great silly talk that you make on a first date. The kind of talk where you know he is going to call you and you want him to call you. Now at this point I am thinking…is this guy going to drive home? I hate people who drink and drive and this would have killed the entire evening. BUT no he left his car and said he would pick it up in the morning.

We hopped in a cab an headed back into the city of Abu Dhabi…and you can imagine the rest. As cliché’ as it is to say it really was one of the best dates ever. 

Runner Up: Sarah’s Beach Proposal
How can it get better than this? On holiday in Cyprus, my boyfriend of 7 years takes me to dinner, then out for some drinks. On the way back to where we were staying, he pulls me onto the empty beach in front of the hotel. We leave our shoes in the sand, and are splashing around in the ocean. He gets down on one knee, takes my hand, and tells me how he wants to spend every day of his life with me. A proposal! (And completely unexpected, I had given up after all that time!) We both lose our shoes on the beach that night, but a small sacrifice for a night that will forever be remembered with a smile. 

Runner Up: Lisa’ Anniversary Date
My best date was with my husband of 14 years and we went out for our anniversary to O’noir.  It is dining in the dark.  The restaurant is in complete darkness and the waiters are blind.  No one in the restaurant can see what you are doing.  The manager says they do not have night vision cameras.  I hope not! We started our foreplay at the restaurant. Hot night continued at home.

Runner Up: Rachel’s Dave & Buster’s Date 
The best date I’ve ever been on was with my current boyfriend. It also happened to be our first date. Not wanting to sit awkwardly through a movie or coffee, we decided to go to Dave and Busters. We drank beer, won prizes, he got his butt kicked at Guitar Hero and Time Crisis, and we played pool for almost an hour. The best part was sitting in the Jurassic Park game (its shaped like a Jeep) and just talking for 45 minutes. At the end, we each came home with prizes that we won to remember the night. It was the perfect mix of nerdy awesomeness and face time, without the awkward silence or mundane conversation. We’ve been dating for almost 8 months now, so I say it was a great way to kick off an awesome relationship. 

Runner Up: Crystal’s Sea Plane Date
I was dating a commercial airline pilot, but had not yet had the chance to see him in action (in every sense of the word). This all changed when he invited me to his cottage for the weekend.  To my surprise, his cottage was situated on a lake, and parked at the dock was a seaplane!   
  
Our date started with a flight on the plane, a landing onto the lake and a (clothing optional) swim.   
  
On the way home, he let me take control of the plane…and when we got back to the cottage I let him take control of me.  

Runner Up: Devan’s Leslieville Date 
The best date I ever had was when I went to go see a room for rent in a townhouse.   

I had been frustrated with trying to find decent roommates for some months, and had given up even looking, when my mom sent me “just one last posting” for a room for rent in a townhouse in Leslieville.    The ad was great, it would be shared with a guy named Casey who worked out of town a lot and needed to rent the second bedroom to pay the rent as well as have someone home to take care of his cat. The photos of the place looked great and I thought of the possibility of having a WHOLE TOWNHOUSE to myself for such a bargain price!  

I made an appointment to go view the place, and when he opened the door, my eyes kind of popped open and my brain went “uh oh.”   

He was THAT cute.  

He showed me around, said he had a few other people to show it to, and would call me with his decision that afternoon.   

He walked me to the café where my mom was having a coffee (she was in town visiting) and met my mom, then she and I went down to the beaches for a few afternoon cocktails and some shopping.  

Casey called 2 hours later. I got the place! YAY!  

Casey suggested I come sign the lease that day, and we could go out for a bite in the neighborhood to celebrate our new status as roommates.  I said sure, and then we could venture over to my cousin’s house in the Beaches for drinks and JazzFest. It would be a blast!  

I signed the lease; we had dinner, jibber-jabbering over wine and snacks for hours, then over to my cousin’s place for more fun.    

I ended up sleeping in the spare room at the townhouse that night (I was in no shape to find my way home) and then he watched Coronation Street with me the next morning.  

A week later we were together.  

Two years later we’re still together. And we’re AWESOME!  

Runner Up: Jenifer’s Puppy Date 
He snuck out of the house while I was asleep so that my day would start with a surprise. I was still asleep before I heard the door open. All of a sudden I could here something to rushing to me. My eyes weren’t open yet when she started licking me and slobbering all over my face. It was the puppy that I kept going back to see at the pet shop. He bought me my puppy and we played with her all day. We watched her slip and slide and charge down the hall. Although it was at home, It was best day/date I had ever had. She’s six now and we’re still together. 

Runner Up: Imnesia’s 21st Birthday Date
It was my 21st birthday and at the time I was dating a Jehovah’s Witness from Michigan; I lived in Windsor. I wasn’t expecting a super special birthday celebration and I was okay with that since my boyfriend didn’t necessarily celebrate. He had told me he had some plans and just to be ready at 5. When he picked me up he had 21 red long stem roses and a card! I was floored. I opened the card and inside was 21 dollars Canadian and 21 dollars in US. Okay, thoughtful and cute check number 2. He hadn’t told me any details of our evening so I was just waiting to see what was next. We went across the border and he surprised me with an awesome downtown restaurant in a private booth away from the crowd. The time he took to make me feel comfortable was apparent all the way through the evening. I’ve honestly never felt so awesome. As night fell we made our way back to his house where he asked me to wait in the car while he stepped inside first. After a few minutes he called my cell to come inside. I stepped into his candlelit kitchen, and through into his living room where a bottle of Moet was sitting atop an ice mountain, along with another card. This card spoke of his appreciation for me, a genuine happy birthday wish and to toast myself with a sip of champagne. It also pointed me in the direction of rose petals that were laid out on the floor. I followed them into his bedroom where they were piled up on the bed and he there stood waiting. On the bed was a gift box of my favorite perfume. At the time it was Coolwater. I know you’re thinking you know what happened next…..we made wild passionate love on the rose petals? Well yes, that was supposed to be the ending. Unfortunately, it was the worst time it could have been for my ‘time.’ Ugh. So, I pitifully explained, more in sadness of my own losing out on wild sex. The amazing guy that he was, he was so sensitive and understanding, we ended up cuddling up on the couch, making out like high schoolers and watching a movie.   By far, my BEST date ever.  

Runner Up: Karen’s Anniversary Surprise
It was our anniversary.  We’d planned to go out for dinner, but unbeknowst to hubby, I’d booked a room at our favourite inn. That afternoon I packed a bag, went and registered us at the inn.  When I got ready for dinner, I dressed casually, but underneath… oolala!! After dinner, I suggested a drive down to the lake.  Imagine his surprise when I turned the car into the parking lot at the Inn.  Imagine his further surprise when he ‘unwrapped’ me.  Needless to say, it was an amazing night!