Project 50 First Dates―First Date #3: Facetious Financier

Welcome to Date #3! “Project: 50 First Dates.”

Let’s go back a few years to First Date #3 of Project 50 First Dates…

Dating site:
Stats: Mid 40s, no kids
Profession: finance

He messaged me this: “Hey, did you used to be in real estate? … Never mind, I Googled you … [something about a risqué Halloween costume from a decade ago …].”

I was thinking: Oh, shit. (And) He’s kinda hot! (And) Wait, I’m sure I’d remember meeting him.

The Rundown:

Somehow, he’d remembered seeing a photo of me in a not-for-public outfit that I wore out in public. (But it was Vegas, baby, so that hardly counts and this was years ago before I became a “classy lady” after all.)

The seeming familiarity of him knowing (of) me lead to texting (which isn’t my thing) and a lot of innuendo (which is my thing).

In the midst of the back and forth, he called me, which is a ballsy move. Kudos.

Hint: Calling a woman out of the blue is a ballsy, sexy move. Do it!

He was witty and fun and way too long-winded, but also facetious and frustrating.

“I haven’t even met you, and you’re irritating me.” I remember telling him.

“I’m just kidding,” he’d offered.

He was needling me about how “a single woman can’t have enough credibility to offer love advice.”

Here’s the rant I didn’t say but thought of saying way after the fact:

“I’ll have you know that there are plenty of people in relationships who haven’t got a clue and who aren’t happy―you want advice from them?

And the most successful dating coach in the world right now is―hello!? Single.


Because love is about being happy (within yourself first), not about being happy only when in a relationship. I’m not hitched, but I am happy, mister! I learned how to love myself, and I know how to fast-track others to the Happy Meadow!

And happy people are more attractive―so, ha!”

The rant I’d actually said, “Women want to know how to get the guy. I know how.”

*Rolls eyes at self for saying such a cringeworthy thing and for admitting it publicly*

He interrupted me with a chuckle: “―you do remember that you’re talking to a potential date, right?”

Hint: Playfully teasing a woman without getting pissy at her audacious behaviour is a ballsy, sexy trait. Do it!

I continued, “Yes, yes, let me finish. I didn’t say ‘any guy’ and besides, getting the guy isn’t a badge of honour. It’s a ‘here’s why you need to love yourself first’ lesson: learn from my mistakes!

They―my exes―were good guys, well mostly, but anyway, they weren’t the right guys for me.

But when you get to a place where you’re whole on your own, you know your ‘Top Five’ and you know how men think―um, that’s valuable info! Wouldn’t you agree?”

He agreed that I am good at sales.

That’s as much as I could get out of him before he went on his own rant about how ridiculous it was for me to “expect any man to want to wait in the queue while I finish this 50 first dates project.”

Ok. Fair enough. He had a valid point.


Social study modification:

If I met the man of my dreams, I’d write about my friends’ first date stories, though I’d have preferred to be with a man confident enough to be OK with my finishing the study if only to give professional feedback to love hopefuls (who weren’t hoping for me).

Facetious and I went on a date.

He was tall, dark and handsome wearing a perfectly pressed business shirt, smartly tailored blazer, dark denim jeans, and what looked like hand-stitched Italian loafers. And he smelled good.

Hint: Having this outfit in your closet and ready to go is sexy AF. Have it!

I’d inadequately planned my wardrobe and showed up in jeans and a t-shirt to a 5-star lounge. *meh*

We talked for two hours. It was an easy, light, fun, and stimulating conversation.

I declined an invitation to continue chatting over dinner because I’d used my own advice and made plans with a girlfriend right after our date.

Even though this first date #3 was mostly a success, would I see him again?

I wasn’t sure at the time, but no, I didn’t. Looking back it seemed he was more interested in my Vegas, Baby personality than the real me.

Either that or he was unimpressed I showed up so shoddy and didn’t continue the date after dinner.

Or who knows, but it wasn’t a loss for either of us because I’d totally forgotten about him until I was updating the post.

First Date #3 Takeaways (written for men but these apply to dames, too):

  1. If you’re engaged in text chatting with enough immediate back-and-forth action to know she’s not busy doing something significant, call her. Ballsy / brave / bold = confidence (real or not) = Sexy. Side note: If you’re the one to call, be the one to end the convo. (See #5.)
  2. Disagreement and differing opinions offer stimulating conversation. As long as you don’t push too many buttons, you may get to her button faster. 😉
  3. Setting standards―I ain’t waiting while you’re dating 47 other men―shows self-respect. Check.
  4. Smell good, but not too strong. One spritz on the chest is enough. Hint: Make her want to get close!
  5. Motto: Always leave them wanting more. Have after-date other-plans.
  6. If it doesn’t work out, that’s A-okay!


P.S. New Just The Tip videos show up first on my YouTube channel―WingmamTV. Subscribe and have educational dating, love and relationship hilarity delivered straight to your in box, so to speak.

P.S.S. Get the woman you really want with my WakeUP2Luv program. Do it!

About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

Leave a Comment:

Death, Dating … Dominatrix? I Am Disturbed. says June 29, 2017

[…] of oneself by displaying one’s ass can make a lasting impression. If you read my original blog, First Date #3: Facetious Financier, you also know I showed up to the high-end venue in jeans, a t-shirt and converse runners because I […]

Dave Olejnik says August 27, 2020

That photo of you in a not-for-public outfit that you wore out in public in Vegas sounds interesting – will you post it?

    Anna Jorgensen says August 28, 2020

    um, no

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