All your dreams can come true if you have the courage to pursue them.

Walt Disney


Cupid’s Escorts is an established female-owned companionship agency that has built a reputation of being honest and reliable. There is a real difference in how we run our agency, we take pride in how we operate, we are ethical, virtuous and honest. Being female owned and operated, we understand what your needs are as a woman and we will always make sure that you are comfortable working within our team. At Cupid’s, we strive to better your life; we provide you with the full support that you need to either continue your education, live debt-free, or enrich your life through any other means possible. Cupid’s Escorts strongly believes in the integrity of achieving your best in everything that you do and believe that every woman has the power to make their lives better. Becoming a professional companion is a stepping-stone to pave your future, please allow us to help you along the way.

Joining our agency can open up many doors for you; at Cupid’s we don’t want you to work for us forever, we want you to work until you reach your goals, dreams and become the woman you want to be. We offer RRSP matching, help pay for your education and also assist in paying for plastic surgery; all so you can feel better about yourself and your future – no other agency can match this. We will put you in contact with accountants, investment specialists, mortgage brokers and business contacts that can assist you with any financial transactions, in an effort to secure your future, allowing and assisting you with any and all forms of making working in this industry the best time of your life.

Our highly organized and professional team of women are here to encourage and support you to along the way. We are a great team of women who are here for you in every way possible. We are not just your agency; we are your support while laying the foundation for your future and we will encourage you to become the woman you want to be.

We are the most ethical and upstanding companion agency in Toronto, and have a near flawless reputation for how we operate.  We take pride in the work that we do and feel that Cupid’s offers the best representation of ladies in Toronto.  Please read our testimonials from our staff, you’ll see why we have remained the top agency in the city for over a decade.

Jillian Hollander

Jillian Hollander

Owner of Cupid’s Escorts

The more you act like a lady, the more he’ll act like a gentleman.

Sydney Biddle Barrows, The Mayflower Madam
What we offer you


  • A higher-than-average hourly wage
  • The flexibility of a schedule that you decide on; there is no minimum or maximum shifts per week
  • Complimentary photo shoot by a professional photographer in a proper studio
  • A safe environment that is stress free
  • The benefit of working with very experienced staff who understand your needs
  • Personal drivers that only drive one to two ladies at a time (safety is our main concern)
  • Female owned and operated agency
  • We will respect your boundaries and limitations
  • Impeccable reputation within the industry for how we operate
  • Extremely well advertised and marketed agency
  • Amazing Search Engine Optimization that has kept us on the front page of Google and other search engines for maximized exposure
  • We do not have an office that you are required to wait at between calls nor will you have to wait in a driver’s car all evening
  • A very loyal following of clientele who know who we are and what we represent
  • Exclusive partnership with a highly regarded cosmetic clinic and spa that offers 30% off  injectables and 50% off skin treatments to all employees
Offers after 6 months of employment


  • We will match your RRSP contribution by 25% at tax time
  • Should you be a student or wanting to return to an academic program, Cupid’s will do what we can to help build your future. If you work an average of 12 shifts per month (minimum of 5 hours of availability per shift), maintain a grade point average of 85% or higher; Cupid’s will pay 50% up to $3,000 toward your tuition per year
  • We will pay 50% of your plastic surgery (up to $2,000 per year), this includes breast implants, teeth whitening, Botox and fillers as well as most cosmetic procedures
  • Cupid’s will gift you $3,000 towards your purchase of a new home or investment property to help with overwhelming costs of buying in the Toronto area

If you are interested in meeting with Jillian – the owner of Cupid’s Escorts for lunch or a meeting to see what Cupid’s can offer you in representation, please contact Jillian directly at jillian@cupidsescorts.ca.

Please keep in mind that we receive over one hundred applications each month to work with Cupid’s.  As a result of this high volume,we ask that you include a detailed description of yourself, your experience that is relative and non-relative to this industry, as well as some non-nude photographs for our consideration.  Emails that do not contain the requested information will not be considered/responded to so please be sure to include this.

There is no time like the present to change your life for the better and we will help you along that way.

Employee testimonials

I want to thank you for your kindness, support and everything you have done. There is a reason you are the best in the business and I am fortunate that I got to work with you. I wish you and the rest of the team nothing but the best.


Working at Cupid's was honestly the best thing that has happened to me. It was the answer to all my problems. All the wonderful people I've met while working here were some of the most amazing, hardworking, inspiring, strong people I've ever known and I'm thankful beyond words that I was able to work in such a great position. I really wish there was another way.


I don't know what you took in school Jillian but you should have a PhD in caring you have been so excellent to us Cupid Girls. Thank you!


It was fate that I landed in your hands - I am more of a woman leaving Toronto then I was when I met you that night. I will never be to truly thank you enough for all that you have done for me. An infinite amount of doors have opened because of you. Thank you a million times;


Due to changing circumstances within my personal life, it gives me great sadness to resign from your agency and the industry. It has been an amazing 5 months working for you and has time ever flown by! I'd like you to know how much I appreciated the opportunity to work for you, and will never be able to express my gratitude. I loved working within this industry mostly because the agency and the people working within it were incredible. Together we all functioned as a family with similar goals. It was an experience that has left imprints on my heart :) I hope in the future if life decides to throw me more curve balls I will be able to slap on my heels and join your team again. As I said from the moment I walked into your office, and as I say leaving, there is no other woman I would want to work for other than you. Again, many thanks :) and I hope to see you around Madame Jillian ;)