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 on calls; we are your support while you lay the foundation for your future.

Our business model is often copied by other other agencies, but they cannot compare with our unparalleled reputation and service.

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 work with Cupid’s Escorts enjoy their status as one of 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; you decide on what hours you want to keep and how long you wish to be on schedule each day; you’re in charge!
  • We offer training for ladies who are new to escorting
  • Complimentary photo shoot by a female professional photographer in a proper studio with many perks like a gifted set of lingerie from high end brands for you to keep and a hair stylist on site, Cupid’s photoshoots standout more than other agencies because of our attention to detail
  • A safe and empowering environment that strives to be stress-free; we believe in work/life balance
  • The benefit of working with very experienced and organized all-female staff that understands your needs
  • Personal drivers that only drive one to two ladies at a time
  • 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 between calls
  • Full respect of your boundaries and limitations; with an understanding that these may change
  • Amazing Search Engine Optimization that has kept us on the front page of Google and other search engines for maximized exposure
  • A very loyal following of clientele who know who we are and what we represent, we have one of the most solid reputations in the industry and have been the leader in this industry for over two decades
  • 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 and out of 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; we 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
  • Cupid’s is very proud to offer a Parental Benefit of $100 for your first child and $50 for each additional child per month to help with the of being a parent, this benefit is available immediately after you begin employment with Cupid’s

“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
Thank you to the amazing Cupids team. My time here has been a life changing experience. Cupid’s clients are some of the kindest and most interesting people I have ever met. The drivers are phenomenal and always there to lend an ear while getting me to appointments safely.  Working for Cupids has changed me for the better.

Compliments from April
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

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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