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 of 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.

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

Walt Disney

At Cupid’s, we strive to help you build a better work/life balance and provide you with the full support that you need to either continue your education, to be financially independent, or to help you find additional ways to enrich your life. Cupid’s Escorts strongly believes in the integrity of achieving your best in everything that you do and believes that every woman has the power to make their lives better.

Our standards for Companions are some of the highest in the industry, and all potential Companions are interviewed and evaluated by our Madame, Jillian Hollander. Our standards also extend to our Clients to ensure your safety and Enjoyment.

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

Perks of being a Cupid’s Escorts companion

Starting from day 1
  • 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 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 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
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
If you are interested in meeting with Jillian – the owner of Cupid’s Escorts to see what Cupid’s can offer you in representation, please contact Jillian directly and in confidence via email: jillian [at] cupidsescorts [dot] ca.

IMPORTANT TO NOTE: Please keep in mind that we receive over one hundred applications monthly to work with Cupid’s. Due to the 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. We keep all your information confidential.

There is a reason Cupids is one of the best in Toronto.

Compliments from
I owe you so much for bringing me into the Cupid's family. During our time together I've learned more about myself and the business worth than I could of imagined. You truly are a matriarch, and I look forward to the day that our paths cross again.

Compliments from Aurora
This is a thank you email to Jillian and her super admin staff. Its almost the end of the year and I just realized how much my life has changed for the better since march of the same year. I am officially debt free and with a small substantial amount saved up. I guess time flies when u are having fun. I am very grateful for this opportunity and support from you all till this day. i love my job and it wouldn't have been, such an exciting experience without you all. This job has given me confidence, friendships and new experiences I would never have dreamed of. I look forward to exciting new things in the new yr and more goals to achieve. Thanks to all the phone girls who dealt with my worrying, freak outs and booking me the most amazing calls. Thanks to Jillian for all the heartfelt phone conversation during some hard times I love you all

Compliments from Adele
I just wanted to send you this email to say thank you. Yesterday afternoon, I went to a TD bank on Bathurst and Bloor and paid off the last bit of my debt! I am now 100% completely debt free! I want to thank you for taking me in and helping me reach my goal. And accepting my silliness and also being so understanding with my schedule, especially with the whole (edited for privacy) life! Now I have a new goal to reach and I'm sure this next year is going to be amazing. Thank you again!!

Compliments from Amelia
I want to thank you so much for the incredible ride that working with Cupid's has been. When I was a little girl I could only dream what being a world class escort would be like! No, really! Having a driver, experiencing world class hotels and exciting escapades; I had a ton of fun! I already miss working with everybody. I made some really great connections. I'm especially going to miss the amazing Cupid's parties! Working with you has given me a lot of inspiration for how I want to participate in the Industry. I appreciate your business ethics and attention to detail. One day I hope to participate in running such a well-organized agency. I will stay connected and will be back in town when not studying hard on my masters in San Francisco!

Compliments from Shay
Certain things in life just change your perspectives towards yourself and the world. Joining Cupid was defiantly one of them for me. April 11, 2013 was the day. Growing up in a strict and traditional home, having 2 degrees on my resume... this industry seems like a huge taboo and no-no. Yet, school didn't teach you how to prevent others to screw your finances, your family couldn't protect you all your life. I had no money in my bank account and no self-esteem in my soul when I called Jillian. I started working a week after our interview. And has it been a life-changing experience!!!!!! Not only the job helped me tremendously - financially, but it also taught me how to work the power balance between men and women. I learned so much more about my body, my sexuality, and most importantly how to say "yes" or "no". Sounded stupid, but it was the simplest things such as standing up for myself which I didn't know how, got me into financial trouble. That, has all changed; because of Cupid, because of Jillian. It was a path which I never thought I'd take, but I'm glad I did. Like I told her once, "Do I regret it? Yea, I regret I didn't do this sooner!" I will forever look at this industry, and my life in a very different way. Thank you Cupid Team: The hardworking Bridgette, the sweetest Faith, and thank you to the one and ONLY Jillian. From the bottom of my heart...

Compliments from Tia
Not only was I on the verge of filing for bankruptcy when you hired me, I was so thoroughly exhausted - mentally and physically - from working 10-12 hour days 6 days a week in some seedy bar or greasy spoon, working for some creepy, pervy loser and having to with scummy customers daily, all for (at best) $100-200 per shift. It was such a struggle to get through each month, and I had no savings to even show for it. In the 6 weeks I have a Cupid, I've gone from too broke, over overworked and stressed to have a life to financially sable and well rested. I've also developed a sense of self worth and peace of mind that can only come from being in control of your life and realizing your goals. It's of no interest to me what anyone's misconceived, negative, wrapped opinions of you is, because I've been lucky to experience the reality; which is that you're an intelligent business woman whose power and achievements came from sincere hard work and being a compassionate and understanding boss. Your success maybe the envy of many others for good reason but you've the amazing you and Cupid's has. Thank you for empowering women in this industry and teaching us the best revenge truly is living well. I will never forget all you've done for me, and my loyalty will always lie with you.

Compliments from Angelina
You're the best boss ever and Cupids has given me a life with financial freedom I've never known and revel in each morning I wake up. It's amazing not having to worry about little things like paying for gas, saving pennies at the grocery store or being able to buy my family Christmas presents.

Compliments from Laura
You really are a miracle worker... I freakin' love my job!!!

Compliments from Alexandra
I'd recommend going to Cupid's to anyone who was down and out the way I was when I started about two years ago. Cupid's gave me a new lease on life the way no other job ever could. It made me a stronger person who has grow to realize that there is nothing in this world that I can't handle. You take scared young girls who in some cases have no where and no one to turn to and then you turn them into strong confident women!! I hope you know how sincere I am being. I feel like I am a success story of how you can totally turn your life around and even start your own business if you keep your head straight and stay professional. I would not have been able to fast track my life in only two years if it wasn't for Cupid's!! In only two years with Cupid's help, I was able to move into a beautiful house, started a business, buy a brand new car and start some night school as well. Cupid's gave me the freedom of time to get my stuff together and then the money to do it! Gyms aren't cheep and if you work all day you don't have time to go! Lol. Hopefully I can help inspire some of the girls to see that Cupid's is a great place to be and that it can help you get a head in life and that you can be here longer than a few months and really make it work for you if you have a plan!! Thank you again for allowing me to make this transition at my own pace and don't be a stranger!!

Compliments from Kara

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