Golden opportunities to work with the best-managed agency


Cupid’s Escorts is an established female-owned and operated Companionship agency that has built a solid reputation for being honest, reliable, and ethical. We understand what your needs are as a woman, and we will always make sure that you are comfortable working on our team. If this is your first time becoming a Companion, if you’re looking to switch from another agency, or you want to return after an absence, we will guide you through the process to make sure this is the right choice for you.

Cupid’s Escorts is made up of a team of highly organized and professional women who believe in empowerment, education, and fun. We are here for you in every way possible. We are not just your agency sending you out on jobs; we are your support while you lay the foundation for your future.

At Cupid’s, we strive to help you build a better work/life balance and provide you with the full support you need to be financially independent, achieve your personal and professional goals, or find additional ways to enrich your life. Cupid’s Escorts strongly believes in achieving your best in everything that you do, we believe that every woman should have the power to make their lives better.

Joining Cupid’s Escorts agency can open up many doors for you; it’s up to you which one you choose to walk through.

Jillian Hollander

Jillian Hollander
Owner of Cupid’s Escorts

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

Walt Disney

Women who are a Cupid’s Escorts enjoy their status as the most prestigious Companions in the country. To see what Cupid’s can offer you in representation, we invite you to contact us directly and in confidence via email: hiring@cupidsescorts.ca

Please note that due to the high volume of applications we receive, 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. No phone calls, please.

All information is kept confidential.

Please note that we do not re-schedule interviews under any circumstance.

Perks of being a Cupid’s Escorts companion

Starting from day 1
  • A higher-than-average hourly wage, one of the highest in the industry
  • 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 strives to be stress-free; we believe in work/life balance
  • The benefit of working with very experienced staff that understands your needs
  • Personal drivers that only drive one to two ladies at a time (safety is our main concern)
  • Full respect of your boundaries and limitations; with an understanding that these can change
  • 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 for your calls at, 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
  • Access to our exclusive library with dozens of titles about sex-work, relationships, money management and how to make the best of your time in the this industry
  • We offer complimentary self-defence workshops to our staff every quarter
  • Exclusive partnership with a highly regarded cosmetic clinic and spa that offers 30% off injectables and 50% off skin treatments to all employees
  • We are the Fully Booked agency; we are here to maximize your time and will book you as much as you are comfortable with
After 6 months of continuous 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/fillers as well as most cosmetic procedures
  • Cupid’s Escorts 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

“There is no time like the present to change your life for the better.
We will be there to help along the way.”

Jillian Hollander
I'm not sure of the exact date I first met you & started with Cupids, but I know it was mid July last year! Wow! A whole year has passed! I just wanted to take this opportunity to thank you from the bottom of my heart for everything thus far. My experience with Cupids over the last 12 months has been amazing! I've learned a lot about myself & life, you have provided me with the chance to live my life my way & I am so very happy & will be eternally grateful :) I was miserable in my 9-5, Cupids has allowed me to take a huge leap by quitting my day job to focus on building my financial portfolio & going back to school (just got accepted for January!) so that one day I will be able to live up to my full potential. You have always been supportive, available & caring, not just for me but all your girls. You've hired awesome phone gals that are just as supportive & caring & drivers that get us to & from safely with a few laughs to ease any tension along the way. You've got a great team & you've done such a good job, I am proud to call myself a Cupid ;) Much love, xoxo

Compliments from Drew
I just wanted to let you know that I am having the time of my life working for Cupids. The clients are adoring and wonderful, and all the staff have been unbelievably good to me. Thank you so much for welcoming me into the Cupids family. I feel very honored & privileged to be a part of the fold.

Compliments from Miranda
I want to thank you for the opportunity to work with you. It was a great ride! Like you said it would be. I am so happy I got to work for you because I feel that you have done a great job at making ''the industry'' a better one. I have no regrets because you made it all work out.

Compliments from Violet
Jillian, Thank you so very very much for everything you have done for me. You have helped me reach a point in my life where I can be happy and free, something unimaginable and unattainable prior to meeting you. You are smart, witty, talented and beautiful! I hope you know how incredible you are! Hugs and Smooches;

Compliments from Kayden
The time has come to tender my resignation from Cupid's. It isn't without a bit of sadness that I do this, what began as a 'means to an end' became a place where I found friendship and support. You and your staff have always been there for me through ups and downs and that is truly what separates Cupid's from every other agency. Your ability to surround yourself with the best people is something that will continue to carry this company forward. Thank you so very much for the opportunity to improve myself and my life. Thank you for never pressuring me for more than I could give and offering me your friendship. During my time here I have been able to achieve financial independence and know what true freedom feels like. Above all else, thank you for believing in second chances. I will never regret being able to have called myself a 'Cupid'. But I will regret going to Mexico with you and being subjected to your non stop midget orgy; that my friend, was a little much even for this seasoned girl.

Compliments from Logan
In only 122 hours you have changed my life. You might not even know it but I am here to tell you so! We don't even know each other well... yet, but one thing I know is that you are one of the most humble people I know. Trust me, there is not a lot of people like that. I want to thank you THANK YOU for letting me be a part of the Cupid's Family... When I met you , I was 1000% sure you were not going to hire me... I guess I was wrong. You made me realize that no matter how scared, unsure or insecure we can be in life to ALWAYS give it a try. Thank you so much Jillian.

Compliments from Zarah
Mistress Jillian; I want you to know how grateful I am to have a boss like you. Every job I've had before you I was never treated well or fair. I have never been happy in a place of employment until I met you. You accepted me as I am and I appreciate that so much. I look up to you as a strong woman and as a friend I can rely on. My loyalties will always be with you. You are beautiful, caring and I love you <3 Also thank you for my set of twins (boobies!), I love them too!

Compliments from Dakota
I first came to work with Cupids 8 months ago. I had been working independently previous to that, but was finding the administration to be to time consuming. I was hesitant about joining an agency but there really was no other choice for me but Cupids. I had seen Jillian's posts on various discussion boards and knew I wanted to work with her. She always stood behind her girls and never took any bullsh!t. I emailed her and she responded almost immediately. We met that evening and I was immediately comfortable. I knew I had made the right choice and I have never regretted it. Now, 8 months later, I consider Jillian as a close friend and am so happy I took the leap to email her. It has all been worth it. She has always been there for me, both personally and professionally, and I couldn't imagine working with anyone else. She is a classy, professional lady who runs a top notch agency. I feel privileged to be considered one of her girls and highly recommend Cupids. Whether you're an independent lady looking for representation, a better agency, or a new girl just starting out, Cupids is the place you've been looking for.

Compliments from Ashton
I've really enjoyed my summer with Cupid's; it helped me financially in a huuuuuge way, it was so flexible, and everyone at work was always respectful and understanding. I could definitely see myself coming back to it. I'd like to thank you so much for being so wonderful to me, and you're frequently in my thoughts.

Compliments from Piper
I want to tell you, all you have been very good to me and I am most thankful. This has gotten me through a tough couple of months and the support I have received from most everyone I met within the company has been amazing. I hope we can say good-bye, knowing that I have learned so much from my experiences. I am most appreciative.

Compliments from Morgan

Get in touch


Cupid's Escorts
Toronto Escorts Cupid's Signature Angel
Office hours




352 Front Street West, Toronto M5V 0K3

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