Personal VA - Dating, Lifestyle & Accountability

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: TYPE OF WORK

Any

: SALARY

$2.5 to $3.5

: HOURS PER WEEK

20

: DATE UPDATED

Sep 19, 2026

JOB OVERVIEW

# Personal VA – Dating, Lifestyle & Accountability

I am looking for a proactive, intelligent, discreet, and highly organized **Personal Virtual Assistant** to help me manage and improve several important areas of my personal life.

This role will focus on **dating and social opportunities, lifestyle planning, calendar management, accountability, health and wellness, travel, and personal projects**.

A major part of the role will involve helping me become more systematic about meeting potential romantic partners. This may include researching and reviewing dating profiles, helping with initial outreach and follow-ups, using ChatGPT to create personalized messages, identifying promising conversations, researching places and events where I can meet people, and helping organize dates and social activities.

You will also help me:

* Research the best social events, activities, venues, and experiences each week
* Manage and proactively organize my personal calendar
* Keep me accountable for commitments I make to myself
* Help organize fitness, wellness, and personal routines
* Research and plan travel and weekend activities
* Track personal goals and results
* Help move personal projects and ideas forward
* Use ChatGPT and other AI tools extensively for research, communication, planning, and organization

I am looking for someone who is **proactive rather than task-driven**. I want someone who understands my priorities, recommends what I should focus on, helps put those activities on my calendar, and follows up to make sure they actually happen.

### Ideal Candidate

You should be:

* Excellent in written and spoken English
* Highly proficient with ChatGPT
* Socially perceptive with good judgment
* Extremely organized and proactive
* Strong at online research
* Comfortable with dating apps and personalized online outreach
* Comfortable managing calendars and follow-ups
* Persistent and willing to hold me accountable
* Discreet and trustworthy
* Able to work independently and make recommendations

Previous experience with **personal assistance, executive assistance, dating or matchmaking support, recruiting, online outreach, lifestyle management, travel planning, or concierge work** is highly desirable.

Experience successfully helping someone generate conversations, introductions, meetings, or dates would be particularly valuable.

### To Apply

Please provide:

1. A brief summary of your relevant experience.
2. How you currently use ChatGPT or other AI tools.
3. Any experience with dating apps, matchmaking, recruiting, or personalized online outreach.
4. An example of how you would hold a busy person accountable for an important personal goal.
5. Your availability and compensation expectations.
6. **A short video of approximately 2 minutes introducing yourself and explaining why you believe you would be a strong fit for this role.** Please speak naturally rather than reading a prepared script. I am especially interested in seeing your communication style, confidence, personality, initiative, and understanding of the position.

Please start your application with **“PERSONAL VA”** so I know you read the full posting.

Applications without the short video may not be considered.

SKILL REQUIREMENT

Personal Assistant Market Research

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Personal VA - Dating, Lifestyle & Accountability

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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