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

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

Like The G Man from First Date #1 (see blog), SS is another gentleman I’m impressed by because … he’s got the balls to go on a fake date, the openness and optimism to “see what happens” and the generosity to share and receive: his story and my fake date feedback. Bravo.

Dating Site: match.com

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

First thing I liked about this man is that he respects my “loathe” of texting, IMing (instant messaging), emailing and so on. (Significant.)

He doesn’t “bother” me all week prior to our date, and I appreciate that he understands I’m busy. He listened, heard and respected my needs!

I follow up with him the day of to confirm plans, and we meet at a fancy dessert house near Gastown on Saturday at 3:00pm, which is a great time to meet—between shifts so it’s not loud or busy.

He’s on time. Early in fact. Check.

He sits with his back to the room. Check. (See last Project: 50 First Dates blog for significance.)

I walk up to him and greet him; we shake hands. I take off my coat and sit down across from him.

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

As I’m saying this, he’s already tucking his phone away in his pocket. Check.

I order a decaf Americano and we agree to share the cheese plate. (TMI and note to self: I will never do a #2 again, as in poop. Cheese does that to me. Sorry, carry on.)

We share stories and cheese but no cheesy stories. He is a gentleman. He avoids eye contact and instead gazes off to the side Heavenward. He slouches, and I have the feeling he feels the weight of the world, despite his easy smile.

He asks how I became a dating coach, and I reply, “I got into the [dating, love and relationship] 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, hey, men need my help—95% of dating site profiles suck!”

He laughs and agrees. “Women’s aren’t so great, either.”

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

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

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

We both laugh.

I tell 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 the one that got left finds out you’re moving on, they’re 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)

We talk for a couple hours, then take our leave. He walks with me on my route home until we come to where he needs to go a different direction to his car. He offers me a ride home (check), and I decline.

We thank each other and part ways. Later, he texts me asking for feedback on how he did: “attractiveness, first impression, personality?”

The Takeaways:

  1. Don’t be afraid to ask for her preferences. Respecting a woman’s communication needs means knowing them.
  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 Stripper 😉 #makeherfeelsafe

Slouchy Stargazer is a solid seven in my estimation. Fix slouching and stargazing, and he’ll get an extra point. (Men like points—and scoring them!)

Additional online dating tips for men here and women here.

Comments welcome!

P.S. Remember how I was thinking about going out with The G Man again? Well, he messed up and made my decision to not see him again way easier. I’ll tell you how in my next blog post for Project: 50 First Dates …

About the Author Anna Jorgensen

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

Leave a Comment: