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

My third official first date for social study “Project: 50 First Dates.”

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

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

The rundown: Somehow, he 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.)

The seeming familiarity of him knowing (of) me leads 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 calls me, which is a ballsy move. Kudos.

He’s witty and fun and way too long-winded, facetious and frustrating.

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

“I’m just kidding,” he offers.

He’s 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. Why? 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 actually said, “Women want to know how to get the guy. I know how. Since I was 20, I got every guy I ever wanted and went for―”

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

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

I continue, “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 agrees that I am good at selling.

That’s as much as I can get out of him before he goes on his own rant about how ridiculous it is 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’s got a valid point.

Therefore! Social study modification: If I meet the man of my dreams, I’ll write about my friends’ first date stories, though I’d prefer to be with a man confident enough to be OK with me finishing this study if only to give professional feedback to love hopefuls (who aren’t hoping for me).

Facetious and I go on a date.

He is tall, dark and handsome wearing a perfectly pressed business shirt, smartly tailored blazer, dark denim jeans, and what look like hand-stitched Italian loafers. I’ve inadequately planned my wardrobe and show up in jeans and a t-shirt to a 5-star lounge. *meh*

We talk for two hours. It’s easy, light, fun, and stimulating conversation. I decline an invitation to continue chatting over dinner because I’ve used my own advice and made plans with a girlfriend right after our date.

Will I see him again? We’ll see.

The Takeaways (written for “him” but all 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, Anna―shows self-respect. Check.
  4. When you’re wearing eau de bold, it doesn’t matter if you’re in a T and jeans in a venue where the cocktail servers are in red carpet couture.
  5. Motto: Always leave them wanting more. Have after-date other-plans.


P.S. If you go to Vegas and wear a Vegas outfit with your arse half hanging out, Facebook will find a way to take what happens in Vegas out of Vegas. Baby. (And yer arse may not be where it once was.)

P.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.P.P.S. Up soon: First Date #4: Not A Stalker.

About the Author Anna Jorgensen

Dating, Love and Relationship Coach Founder: Wingmam, Vancouver, Canada Warning: Not PC, not a feminist ❤️

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