word on the street

Jack is an amazing dog walker!

He treats my Andi as if she was his own dog. He is mindful of all issues that might cause concern while dogs are in his care (weather, other dogs, potential problems given the environment at the time. ) Thumbs up!!

Annie Reid

It was an absolute pleasure working with Jack!

From the beginning, his main concern was ensuring my vision and the shots I wanted were captured.  His communication was excellent and he went far beyond any expectations I could have had in working with a dog photographer.
Our photos turned out really great. 

Although the dogs didn’t give us much to work with, Jack made it happen all the same and we are thrilled with the results.  He captured the dogs spirit as well as their antics in the perfect way.   The quality of shots reflected his passion for both dogs and photography. Jack is a true professional and an excellent photographer. 

I highly recommend working with Jack, so much so, that we have already booked another session.

Hayley Greenberg

Jack is THE best dog walker I’ve ever used.

I have A very high energy Border Collie, who needs a lot of exercise and attention. Since meeting Jack, it’s helped me a ton with keeping her active and engaged. His walks and doggy dates to the beach gets Neymar (my pup) so excited and exhausted by the time she gets home.

Jack treats her like his very own dog. He is truly passionate about animals and puts 110 percent into work. I highly recommend him!

Andrea Guindon

Thank you Jack and Jet!

Jack of DoggyDates was recommended to me through the excellent and trusted team at the Bone House on Queen St E. Jack has now looked after my senior dog (15 yrs old) on four occasions over the past 5 months, including 3 extended overnight stays, and I could not be more happy to have found such a caring and committed person to leave Ally with, as Jack.

Jack and his adorable boxer puppy, Jet, treat Ally like a member of the family. I receive regular updates from Jack, and it is clear to me that she is always extremely well taken care of with lots of love.

The care of my dog is very important to me and I could not recommend Jack more highly.

in the news

When Your Doggy Is Your Date

Valentine’s Day is just around the corner – some people are excited to celebrate with their significant other, while others are planning some quality time with their significant pet. Who needs to go out during the craziness of Valentine’s Day dinner, especially with all this snow and salty slush here in Toronto. If you are planning something small and intimate with your pup (with or without a human SO), then we suggest supporting a local business in Toronto called ALLJACKEDUP! (read more).


My new HERO, and yours!

Good Monday, fine followers! This Bloggy Monday, I am honoured to highlight a human who just pretty much became my favorite dog photographer, bar none! Also an entrepreneur several times over, and an all-around great person – intelligent, humble and a great talent. Those of you in the Toronto area, take note! Jack and I are talking about a possible collaboration in NYC in the Fall so stay tuned. (Read more)



Get Leashed Magazine Spotlight

Entrepreneur JACK JACKSON has been spreading a message of love in Toronto’s transgender community and gaining visibility worldwide as an official partner of the Ties to Love™ Campaign, after moving to the six from the UK. As a fiercely proud Torontonian, a passionate advocate of transgender issues, and talented ACCESSORIES designer for both humans and dogs, Jack has some new ventures on the go that we are excited to share with you. (read more)

your diamond in the rough

We offer 3 photography packages


1. Paparazzi


  • 30-minute telephone pre-shoot consultation
  • 2 hour photo shoot session time
  • Private online gallery, with 10 edited images
  • 8 web optimized digital files with the option to purchase all ten

2. Going Famous

$595  (our most popular)

  • 30-minute telephone pre-shoot consultation
  • 2-3 hour photo shoot session time
  • Private online gallery, with 17 edited images
  • 12 web optimized digital files with the option to purchase all 17
  • Post-shoot meet-up to discuss printing solutions
  • 1 metallic print wall art, 16 x 20 inch ($279 value)
  • $50 printing credit

3. Movie Star for a Day!


  • In home or on location pre-shoot consultation
  • Two 2-3 hour sessions in 2 different locations
  • Private online gallery, with 20 edited images
  • 16 web optimized digital files with the option to purchase all 20
  • Post-shoot get together to discuss printing solutions
  • 1 metallic print wall art, 16 x 20 inch ($279 value)
  • 1 acrylic print wall art, 20 x 24 inch ($269 value)
  • 1 Desktop acrylic block, 5 x 7 inch ($179 value)
  • $50 printing credit
  • Additional dog, add $50, (maximum 2)

Need something different? Hi, I'm Jack, founder of Doggy Dates. Let me know what you have in mind, and we'll tailor a shoot just for you. Contact me.

Don’t You Want Me Photo Project

Don’t You Want Me is an ongoing, celebratory collection of narratives and photographs of the queer and trans community and their rescue dogs. The project shows the powerful bond between subjects who’ve endured considerable hardships and are now not only surviving but flourishing.

Check Out The Project >