Project 50 First Dates — First Date #2: Slouchy Stargazer

My 2nd Official 1st Date for Project 50 First Dates

Many years ago when I’d just started coaching, I launched Project 50 First Dates, and was offering “real fake date” coaching options.

Like The G Man from First Date #1 (see blog), SS was another gentleman I was impressed by.

He had the balls to go on a real fake date, the openness and optimism to “see what happens” and the generosity to share and receive: his story and my real fake date feedback.


Let’s explore what happened and see if the advice I gave still applies in today’s dating scene!

Dating Site:

Age: late 40s
Kids: two—tween and teen(age)
Work: executive management

The first thing I liked about this man was that he respected my “loathe” of texting, IMing (instant messaging), emailing and so on. (Significant.)

He didn’t “bother” me all week prior to our date and I appreciated that he understood how busy I was.

He listened, heard and respected my needs!

I’d follow up with him the day of the date to confirm plans and we met at a fancy dessert house not too far from where I lived at the time.

The date was on a Saturday at 3:00pm, a great time to meet between restaurant lunch and dinner shifts so it’s not loud or busy.

Right away he got two points! (Don’t deny it, men love scoring! 😉 )


  1. Was on time. Early in fact. Check. (But no need to be early without reason.)
  2. Sat with his back to the room. Check. (See last Project: 50 First Dates blog for significance.)

I walked up to him and greeted him; we shook hands.


Even in today’s #metoo era, I suggest asking if she’s “a hugger” as it’s always a good idea to break the appropriate touch barrier sooner than later.

I took off my coat and sat down across from him.

Right off, I placed my cell phone on the table face up and apologized, “I’m so sorry, but I’m waiting for a call from my banker that is urgent.”

Anyway, as I was providing my excuse for having my phone rudely out, he was already tucking his phone away in his pocket. Check.


When you’re on a first date, give your date your whole attention unless urgent and disclosed.

Urgent = sick kid at home or loved one in hospital or getting mortgage confirmation on place you’re buying. “Time is of the essence” type of stuff.

I ordered a decaf Americano and we agreed to share the cheese plate.

We shared stories and cheese but no cheesy stories.

He was a gentleman, but avoided eye contact and instead gazed off to the side Heavenward.

Also, he noticeably slouched and I had the feeling he felt the weight of the world despite his easy smile.

He asked me how I became a dating coach and I replied, “I got into the business after years of obsessive study, testing theories, practicing strategies, and fine tuning … but it wasn’t until I went on [dating site] and was sorely disappointed by the photos, write-ups and communications that I realized men need my help—95% of dating site profiles suck!”

He laughed and agreed. “Women’s aren’t so great, either.” (True!)

But he had a positive attitude about his last relationship, “The girls are handling it well, the split. I take them to school …”

I found out that he was only a few months out of a marriage and “not quite divorced” as in: “not even legally separated yet.”

“Ahhh,” I said, trying to recall if I read this disqualifier in his profile or if I’d missed it, “So, you’re really fresh meat!”

We both laughed.

I told l him not to be too quick to settle down again, “It’s okay to get out there and taste some different ice-cream flavours. Just don’t tell your girls until you’re divorced! They’ll tell mom, and she’ll make you pay.”


I sold real estate for 20 years. I saw a lot of divorces. When she finds out you’re moving on, she’s not all: “Oh, that’s cool, here let me be generous in our settlement so you can spend our money on your new sweetie.” #truth

This also applies to bitter fellas feeling hurt if she moves on first.

We talked for a couple hours, then took our leave.

He walked with me on my route home until we came to where he needed to go a different direction to his car.

He offered me a ride home (check), and I declined. Women always have safety first at the forefront of their minds.

We thanked each other and parted ways.

Later, he texted me asking for feedback on how he did on “attractiveness, first impression, personality?”

The Project 50 First Dates Takeaways:

  1. Don’t be afraid to ask for her preferences with regard to communication. Respecting a woman’s communication needs means knowing what they are.
  2. Know that dating sites are the first place single people who are “back on the market” go to get back into dating. Understanding this means asking the right questions before you meet—are you up for fresh meat?
  3. Be honest about your relationship status. You’ll have a better chance of meeting someone in the same place emotionally and not disappoint nor be disappointed.
  4. Forge your own path—without “oversharing” with your past partner—when you’re going through a legal “sedation” or divorce. Divorce requires delicacy in the delivery of information, especially when children are involved. Most breakups are highly emotionally (and often negatively) charged. Let’s face it: even though you were supposed to share everything with that person while you were with them, you didn’t. Don’t start now. P.S. If you want to sleep well at night, be fair in the settlement. (You know what that looks like.)
  5. Always offer to walk or drive your date home. That’s called being a gentleman. Understand that, if it’s the first date, she just met you and doesn’t know if you’re a John Ritter or Jack the Ripper 😉 #makeherfeelsafe

Slouchy Stargazer was a solid seven in my estimation.

Fix slouching and stargazing would get him an extra point.

xo AJ

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If you want to get the maximum points possible so you can score the best gal for you, get my WakeUP2Luv program today!

Think you’re all that and a bag of kettle chips? Ok, fine, but if you’re on a dating site, guaranteed your profile needs work. Get my Double Your Online Dating program here. Cheap like borsch!

About the Author Anna Jorgensen

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

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1 comment
Fazal Mayar says July 12, 2020

Great stuff anna, 7/10 means it didn’t go bad 🙂

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