Are you an excellent writer with an intuitive understanding of people? Ever thought about being someone’s modern-day Cupid? A successful Chicago business owner is looking for a smart, witty, and organized assistant to help navigate the world of online dating. This role blends writing, matchmaking, and social coordination — a mix of creativity and strategy.
WHAT YOU'LL DO:
Craft thoughtful online dating profiles that best reflect the client across multiple platforms.
Write engaging, authentic, and polished messages to potential matches.
Curate and coordinate fun, stylish dates around Chicago.
Keep everything organized, professional, and completely confidential.
WHO YOU ARE:
A strong, playful writer who knows how to capture personality.
Educated, articulate, and emotionally intelligent.
Ideally female, with an intuitive sense of what resonates with women.
Based in Chicago, with local knowledge of events, restaurants, and culture.
Reliable, discreet, and genuinely interested in people and relationships.
THE DETAILS:
Part-time, 10–15 hours per week.
$35/hour.
Flexible schedule, with most work done remotely
HOW TO APPLY:
If this sounds like the right fit, please reply with:
A brief note about why you feel qualified for this role
Your resume (if available)
A recent photo
All applications will be carefully reviewed and personally responded to by the business owner. Selected applicants will be invited to a Zoom video interview or an in-person meeting at his Lincoln Park office.
Requirements for the selected candidate:
Provide a valid government-issued ID
Agree to a background check
Sign a confidentiality agreement
If you’re sharp, witty, and love words + people, this could be the most fun and rewarding job you’ve had.
