Can't Get a Date? Hire a WingWoman

Your love-finding sidekick.

This Week: We explore the odd gig of being a wingwoman / wingman.

Today, we’ll chat about the unusual job of being someone’s wing-person as they navigate the challenging world of dating. On Wednesday we’ll profile how one person makes their income by being a full-time wingwoman. On Friday I’ll share odd jobs hiring the wingwoman/wingman space.

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The closest I ever got to a wingwoman was when I crawled into the office of a matchmaker.

I was dateless, hopeless, and pretty sure I was going to live a loveless life.

I had tried dating apps. I had tried letting my mom micro-manage my dating apps. I had even tried out for the Bachelor (TV show) because I was so eager to meet my match.

Nothing worked.

I was about to give up when I found a Groupon (remember how big those were back in the day??) to meet with a NYC matchmaker. I left a pile of nervous sweat outside the door to her office, went inside, answered a bunch of strange questions, and was set up on a date with someone I crossed my fingers I’D NEVER SEE AGAIN.

He was awful.

But the experience?

It was sort of great.

It got me to answer questions I never thought about and it made me feel like if dating was approached with more of a strategy, and a sidekick, I could probably be a lot more successful.

It gave me a confidence kick in the butt.

A year later, I did another wild experiment where I went on 14 dates in one month. I met nobody. I went on date 15 and guess what?

I married date 15 (Hi, Adam!!!)

Which is to say I believe in love and I believe in odd approaches to finding love.


What the heck is a WingPerson?

It’s a person you can hire as your dating sidekick, teaching you flirting tips, practicing body language, optimizing your dating profile, helping you with conversations, and so much more.

What's the pay like?

You could essentially charge whatever you like for this kind of gig - as long as you can prove value, results, and your unique approach.

Here are some examples:

Hire a WingWoman charges $72 an hour, with a two-hour minimum—every half hour after that costs $32.

Erin Davis Wingwoman charges an hourly fee of $150.

If I was doing this bizz, I’d make it a package deal.

Example: The WingWoman Gold Package

  • Dating profile re-do and photo session with NYC famous photographer

  • Dating profile message management and response service

  • (3) 1-hour phone calls as your WingWoman

  • (3) in-person nights out as your WingWoman (2-hour max)

    I’d throw in some extras (books, access to a FB group, etc.) and charge $2,500 for a 90-day service.

What kind of skills do you need?

You’ve got to be someone who loves love, loves people, loves socializing, loves meeting new people, loves conversations, loves connection, and loves talking.

Also, you probably should be the kind of person who can walk into a room where you don’t know anybody and leave with a million new best friends.

Is it fun?

I’ve found that a lot of jobs with catchy and fun titles to them are usually really tough and exhausting.

While being a wing-person probably has it’s perks for a person who likes to go out, hang with new people, and is a true extrovert, I bet it has downsides.

All your social nights you’d spend with friends would be spent with clients and after a while, doing your job would feel repetitive and I imagine a bit boring.

Can you make a lot of cash?

Remember, it’s one thing to have an odd gig as a weekend side hustle, but if you really want to make the BIG cash - you need to make the job scalable.

I imagine, after a few years of being a wing-person, you get burnt out. A lot of the wing-people I looked up seemed to have pivoted their businesses or ended it all together.

To make the big money, you need to scale and you can’t scale yourself.

So you’d have to:

-Hire other wing-people

-Sell a book

-Sell a course

-Sell merch

-Sell retreats or events

-Become an affiliate or sell ads

-Create a podcast or TV show

-& more.

It’s a job that’s a lot of hustle and will require multiple streams of income within the business.

Leave a comment

Would you ever want to become a wing-person?

Ps. I’ll be back Wednesday with a profile of a person who is making $$$$$$ just being a dating sidekick.

-Jen (odd) Glantz


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