Project: 50 First Dates aka AJ—Master Dater

Project: 50 First Dates … Gents: Wanna Date Me?

Here’s a chance for chivalrous men to—Meet Your Match(maker)

Let’s get right to why I’m going on 50 first dates: How many people are you attracted to in the real world? Not that many, right? Right. And how many people are you dating in a week? a month? a year?

Do the math:

Hypothetically, if you’re attracted to one in a hundred and dating one a week. (Which we all know you’re not.)

Then survey says … Ladies: cats. Gents: Pornhub.

The other day when I was explaining this to a client, I had this realization: cats!

That’s when I realize I’m not following my own dating advice! At the rate I’m dating, I have a future with cats.

So, I call my friend, Jane Carstens, founder of Matchmaker For Hire. Yep, she’s Vancouver’s premier matchmaker. And yep, she’s been on Housewives of Vancouver. (That’s TV, y’all!)

“Jane, I want to do a social study on single men on dating sites. I’m taking my own advice and dating as many men as I can, and I want you on this project.”

As a fourteen-year veteran in the Vancouver matchmaking scene, Jane is intrigued. We schedule a meeting.

When we meet and settle in with our lattes, I tell her, “I don’t want to be a matchmaker. I prefer helping singles get ready to get set to get dating. And to teach them how to date better. From the feedback I’ve received from both men and women, people need a lot of help in this area.”

“Okay.” She nods.

Jane matches quality singles, but even quality singles screw up on dates. She advises them with filtered feedback, but of course she’s not actually out on the date with the couples.

I continue: “Since I am single and open to love, I’m going on 50 dates.”—she raises an eyebrow—“As long as they meet my Top 5, I’ll take the chance. If there’s no connection, I’ll learn something, meet some good men, and give constructive feedback that’ll help them for their next date, which helps women, too!”

“How can I help you?” She offers kindly.


So here’s the dating deal:

I date the guys. At the end of the project Jane will select one man to give a six-month trial Matchmaker For Hire membership. (Value $2,000!) The other gentlemen may receive a free consultation with Jane.

Participation criteria:

  1. The men must meet my Top 5. (I am looking, after all.)
  2. A short (maximum 250 word) essay on: Why They Deserve Cupid’s Bow. (Email to me here.)
  3. Be gentlemen on the dates—whatever that looks like for them.

So …

Here are my Top 5 Must-Haves:

  1. Honourable: Does the right thing even when no one will find out.
  2. Affectionate: For the purpose of this project, keep your hands off.
  3. Financially responsible: No debts, no creditors.
  4. Intellectually Stimulating: Knows something about something.
  5. Healthy. Mind: you learn; body: you’re kinda fit; spirit: you love your enemies.

Wanna date?

50 first dates

I know what you’re thinking: cats. This lady better like cats! I’m okay with that, and I can reciprocate my Top 5.

I know my Must-Have list is a rather tall order, but it’s damn close to what most women want (though affection requirements vary).

The other thing most of us want is tear-each-others’-clothes-off chemistry. Again, for the purpose of this project, that won’t matter. Refer back to #3: hands to self.

What does matter is that you’re open to having easy conversation about what you want in a woman worth holding on to, being your true self and keeping an open mind.

Remember the movie What Women Want? This is the What Men Want version. (Minus the film crew.)

Afterwards, I’ll report my findings. (Identities confidential.) And maybe we’ll get a TV show! Or a sponsored web series. Get on Breakfast TV? Make a YouTube video?? Fine, I’ll take a selfie and pretend I was on TV.

I’m doing this for love, people! Because love is the answer!

Ladies, add your burning questions that you want me to ask these gentlemen in the comments below!

Gentlemen, are you willing learn something from a girrrrl or teach a lady something about what men want? Or maybe—maaaaybe—meet your match?

No guts = no glory. And no: Ma’am.


The fine print:

  1. No creepers, no mental illness, no married or “not legally separated” fellas.
  2. Only men between 40 and 55 years young. (Under 40: unless you want kids, you should still be testing “ice-cream flavours.” BTW: I’m 45-ish.)
  3. Coffee, lunch or dinner—you pony up for eats. You’ll get free feedback worth ten times the price of the excursion. (I’ll be gentle.)
  4. You give location options in Downtown Vancouver. I choose and meet you there.
  5. I reserve the right to add any other qualifiers and/or to exit early if you’re an irreparable douchebag.

Who’s first?


p.s. If I do meet the love of my so-far-cat-free life, I need you to accept that I’m finishing this project! But no worries, Sugar Plum, refer back to “hands off.” *kiss kiss*

p.p.s. My Top 20 can be found here on my personal blog. Warning: not PC plus swears and shit.

Cut to next scene: “Here, kitty kitty …” (shakes bag of Whiskas).

About the Author Anna Jorgensen

Vancouver Matchmaker and Dating, Love and Relationship Expert
Founder: Wingmam

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Project: 50 First Dates aka Wanna Date Me? says June 29, 2017

[…] Wanna date me? You’ll have to visit to find out how! And find out the bonus prize from local matchmaker, Jane Carstens, owner of Matchmaker For Hire. […]

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