FAQs

I’m Jillian, owner and operator of Cupid’s. I walked into this industry in 2004 when I purchased a modest agency called Cupid’s Candies, long before it was fashionable to talk about empowerment, workers’ rights, or ethical standards in this space. What followed was two decades of quietly reshaping expectations — from introducing and creating programs rarely seen anywhere in the adult companionship world: I began to introduce structured benefits and support programs for women, including professional development, wellness initiatives, financial planning options, and meaningful protections that extended well beyond the norm. All of it was designed not just to compete with other agencies, but to elevate what this work could be — because if women are going to be here, they deserve dignity, choice, and real support.

Cupid’s became more than a business — it became a reference point. For years, other agencies have quietly measured themselves against the standards we set: professionalism, discretion, longevity, and the ability to consistently operate at the top of the market. Remaining there requires restraint, discipline, and an unwillingness to compromise — qualities I’ve maintained while the industry around me shifted, splintered, and rebranded itself repeatedly.

It’s been a long, unconventional education — equal parts business, advocacy, and serendipity — with content that could easily fuel a Netflix mini-series. Until Jeff Goldblum decides to play my love interest, however, I’m respectfully declining all production offers.

Yes, of course. The safety of everyone in this industry is something we strongly believe in. We only provide references if you have used our services within the past six months.

That’s a fair question — and one we hear from time to time. This industry isn’t regulated in the way many others are, which means experiences can vary widely from agency to agency.

Cupid’s has been operating for over two decades, and longevity at this level doesn’t happen by accident. Our reputation has been built on consistency, discretion, and accountability. We work closely with our Companions, we know who we represent, and we stand behind the experiences we arrange. If something doesn’t feel right, you’re not left navigating it alone — our office is involved, responsive, and invested in resolving concerns appropriately.

Many of our clients came to us after disappointing experiences elsewhere and have stayed with us for years. While no agency can promise perfection every time, we can promise professionalism, clear communication, and a genuine effort to ensure your experience meets expectations.

No, we do not provide dancers or entertainment for parties and none of our Companions know any magic tricks.

A little shy? That’s fine. Use 416-532-4603 to reach us by text.

Yes, we finally got up to date with technology after 22 years, and you can SMS us now.

We’ll ask for a brief description of what you’re wearing and pass that along to your Companion. You’ll receive a call as she is pulling up so you know to go downstairs.

You’ll meet your Companion in the lobby. If you prefer to remain discreet, she can be advised to quietly follow your lead to the elevators. From there, you’ll head upstairs together. Simple.

Yes, of course. We don’t screen by colour — we screen by behaviour.

Cupid’s does not work with anyone who discriminates against clients based on race, background, or identity. Toronto is one of the most multicultural cities in the world, and we proudly welcome clients from all walks of life.

As our Companions are available for local and international bookings, we recommend that you make your request as far in advance as possible. We do our best to accommodate bookings up to several months in advance.

Same day bookings are available (subject to a Companion’s availability) but we ask that you phone for this type of booking, and provide us with at least a one hour grace period to ensure a Cupid’s Escort is able to come to your hotel or residence without being rushed.

Not at all! We won’t shy away from what makes you unique, and many of our ladies love seeing clients of varying abilities. Please let us know of any special arrangements at the time of booking, and feel free to search our portfolio to find a Companion who suits your tastes.
Disability Friendly

No. Cupid’s is not an in-call agency. If that’s what you’re looking for, we may not be the right fit — and that’s perfectly fine.

Yes, all of Cupid’s Escorts Companions accommodate residential, short-term rental and hotel calls. Please note that we do not service motels.

Of course! Our Companions are experienced and elite travellers. We ask that you email us as far in advance as possible, to book your preferred travel Companion. We will ask that you provide us with as much detail as possible so that we can make the appropriate arrangements (e.g. scheduling, vaccinations, etc.). Please visit our Travel section for more information.

Our Companions’ schedules come in on Saturday evenings and are posted Sunday early morning, and it is recommended that you book your desired Companion at that time by calling or emailing our office.
Should you wish to make a booking before the schedule becomes available, you can send us an email with the date and times you are looking for and we can check a Companion’s availability in advance for you.
Out of respect for their time, we not ask ladies to see anyone once their schedule has been submitted.

First Time ClientsWe’ve created a special page filled with tips and suggestions for those booking for the first time.

We stand strongly behind all ladies we represent and cannot recommend one lady over another as everyone has their own specific preferences. We have exceedingly high standards in who we hire and represent, and feel you will be very pleased with our service. Our portfolio is fun to browse and any specific questions can be addressed by calling in to inquire.

Cupid’s like to turn heads, not raise eyebrows; it is not our business to draw unnecessary attention to ourselves. When entering a hotel or residence, they will be discreet and very well dressed for the occasion. Under no circumstances do we wear anything casual, which includes denim, workout gear, sneakers, or flip flops.

We do take appropriate clothing requests at the time of the booking. No one wants to show up in business casual at the theatre, darling!

Our Companions are always appropriately attired and are strong believers in personal care and hygiene. We ask that you extend the same courtesy to them in return and be prepared for their arrival.

If you are having someone at your home, please have fresh towels and present your home as you would to someone you wanted to impress. During our bitter Canadian winters, shovelling your walkway/driveway would be very courteous as well.

We ask you have an envelope ready for the Companion with the requested donation in plain sight; it’s bad manners to make her ask for the gift. Tsk tsk.

We suggest some of the following activities to enhance your time with Cupid’s Escorts:

Dinner at a restaurant you’ve wanted to try
Sharing a bottle of fine wine or sparkling water in front of the fire – provided it’s unopened at the beginning of your encounter
Discussing the meaning of life
Building pillow forts
Artisanal candle shopping
Playing musical chairs
An in depth discussion of Van Gogh’s Yellow Period

If you need help planning your encounter, feel free to look at the ladies page for what they have listed for Date Ideas.

House Accounts are available with a minimum purchase of $10,000.
As a thank-you for your loyalty, Cupid’s will provide a 10% top-up on all House Accounts.

Cash is always preferred but yes, we do accept EMT’s from Canadian accounts.  Please mention this at booking as the EMT must be received prior to arrival as we use a different email address for everyone’s privacy. Please contact us for details.

For discretion and convenience, we accept the following forms of payment:

Cash
Preferred for in-person bookings. Please have payment prepared at the start of your appointment.

Email Money Transfer (EMT / e-Transfer)
Secure and commonly used. Instructions will be provided at time of booking as we use a discreet email for these transactions.
Transfers must be completed and confirmed prior to the appointment.

House Accounts
Clients may maintain a pre-funded account with Cupid’s for seamless booking.
(See House Account policy for minimums and loyalty top-ups.)

Gift Cards / Prepaid Cards
Select prepaid gift cards may be accepted with prior approval.
Please confirm with the office before purchase to ensure compatibility.

Yes. Tipping is always appreciated but never expected.

Our Companions are presented with tasteful, professionally-produced images that reflect their elegance and personality and the published photos are the ones they have allowed us to share of them. We do not have any additional photos of any of the ladies.

No we will not. We believe that discretion works both ways and strive to protect privacy as much as possible. We can assure you that we have high standards with whom we represent.

Yes. We work with a wonderful photographer who takes all of our Companions’ photos. Both Jillian and Cat personally arrange for and supervise the photo shoots of each lady once they join the Cupid’s Escorts roster – it’s one of the many perks they enjoy once they join the team. Photos are updated annually.

Celebrity and public figure confidentiality agreements are more than welcome, as long as they include provisions to protect the privacy and safety of the Cupid’s Escorts team.

No we do not keep client information. However should a Client violate the terms and conditions of an encounter with our Companions, we will keep that Client’s information on our blacklist – i.e. that Client is no longer welcome to book a Cupid’s Escorts Companion.

Do people still videotape things these days anything aside from silly dance Tiktok videos? To answer your question: no. We want to ensure that everyone has a good time and that everyone’s privacy is protected. You’re welcome to Tweet a picture of your meal, but not your dinner date. That privacy protection goes both ways. Our Companions will not photograph/videotape you either. Any violations of privacy or safety will be reported to Toronto Police Services.