Dating assistant

Dating Concierge & Dating App Assistant

Katie’s Dating Concierge is a premium dating concierge service helping successful, busy men take the work out of modern dating. We handle everything from dating profile management and daily swiping to conversations, screening matches, and arranging dates.

We are looking for a confident, outgoing and socially intelligent woman to join our team long-term.

This is NOT a typical social media or customer service position. You will be communicating with real people on dating apps and with our clients, so you need to be naturally good at conversation, flirting, reading people, and creating genuine chemistry.

What you’ll be doing

Dating App Management

• Manage clients’ dating app profiles and swipe through potential matches.
• Match with women who are a good fit for the client.
• Start and maintain conversations with matches.
• Flirt naturally and confidently while keeping conversations engaging.
• Get to know the women and determine whether they are a good potential match for the client.
• Move conversations toward setting up an actual date.
• Keep track of conversations, matches, and dates.
• Represent the client professionally and in a way that feels natural — the goal is to make the interaction feel authentic, not robotic.

Client Communication

• Communicate directly with our male clients.
• Help onboard new clients and make them feel comfortable using the service.
• Give clients regular updates about their dating activity, matches and progress.
• Answer questions and communicate throughout the dating process.
• Build a comfortable, positive relationship with clients.

Because you will be representing Katie, you should have a warm, confident and slightly flirty communication style with clients as well. Our clients should feel comfortable, appreciated and excited about the service — never embarrassed or awkward about having someone help them with dating.

The ideal candidate

We are looking for someone who:

• Has perfect or near-perfect English and excellent communication skills.
• Has a **clear, natural English accent and is very easy to understand.
• Is confident speaking English — you must be comfortable sending voice messages and speaking with clients.
• Knows how to **flirt naturally and keep conversations fun and engaging.
• Is comfortable talking to both men and women.
• Has strong social skills and can read the tone of a conversation.
• Is outgoing, confident and not shy.
• Understands dating, attraction and modern dating culture.
• Ideally has personal experience with dating apps and understands how people actually communicate on them.
• Can keep multiple conversations organized without losing track of details.
• Is reliable, mature and professional.
• Is comfortable representing someone else online and staying consistent with their personality and communication style.
• Has a good sense of humor and knows how to make people feel comfortable.
• Is looking for a serious, long-term position, not a temporary side job.

Important

Personality is extremely important for this role.

We don't want someone who simply knows how to type messages. You need to understand how to create attraction, how to flirt, how to keep someone interested, how to move a conversation forward, and how to make people feel good talking to you.

If you are naturally charming, confident and social, you will probably enjoy this job.

Schedule

• Tuesday – Saturday
• 5 hours per day
• 25 hours per week
• Working according to Toronto time (EST/EDT)
• Fully remote / online

Pay
$5 CAD/hour

This is intended to be a long-term position for someone reliable who wants to grow with the company.

Requirements

• Laptop/computer
• Reliable, fast Wi-Fi
• VPN
• Quiet environment where you can communicate professionally
• Excellent written and spoken English
• Ability to send voice messages
• Availability Tuesday–Saturday during the agreed working hours
• Strong attention to detail
• Comfortable using dating apps and communicating online

How to apply

Please send us:

1. A short introduction about yourself.
2. Your previous work experience, especially anything related to dating, customer service, sales, social media, communication or online work.
3. Why you think you would be good at this position.
4. A short voice recording introducing yourself in English. We specifically want to hear your English, pronunciation and communication style, so please do not skip this step.

If you read the entire job description, include the word “king” in your response message.

Applications without a voice recording will not be considered.

Dating App Test

We want to see how you naturally flirt and start conversations. Based on the profiles below, write the first message you would send.

1. Dani, 28

“I can’t date Theo Von so I’m here instead”
Graphic Designer
“I’m stronger than I look”
“I can beat you at being early for everything”

Your opener: _______

2. Miri, 26

“Carrot cake defender”
“Message me if you also love… carrot cake”
University of Toronto
Leo

Your opener: _______

3. Ray, 31

Senior Manager in Consulting
“Blindfold me and tell me 60h work week isn’t healthy 🥱”
“First date wish list: Tennis pls play tennis with me 🥹”
Has a dog

Your opener: _______

4. Follow-up

Her profile: “Drinks on me if you guess where I’m from.”

We sent: “How about drinks on me, and you tell me where you’re from? 😊”

She replied: “Lmao great workaround”

What would you reply? _______

We are looking for messages that are short, natural, playful and flirty — something that would genuinely make the person want to respond.

Please do not use ChatGPT or AI for this test. We want to see how YOU communicate.