50 First Dates—First Date #1 (New video!)

Project 50 First Dates — AJ: Master Dater

Several years ago, obviously when I was still “on the market” and single, I embarked on a 50 First Dates project.

I thought I’d go back to my first official date for the social study and share the findings in story time format.

Yes, I did tell him the what’s-what and he agreed to meet me, anyway.

Dating Site: match.com

Age: mid-50s
Kids: two; grown & gone
Work: government; upper management

We’d agreed to meet at a lounge-y—uh, well—lounge near my residence at the time.

It was raining.

I walked over to the venue only a few blocks away as the rain squished the traffic exhaust fumes into the greasy pavement.

The air was fresh, refreshing.

It was a Thursday at 5:00pm, so the venue was almost empty when I arrived and my date was easy to spot at the bar.

He stood as I walked toward him while shaking out my umbrella. He stuck out his hand to shake mine, but I swooped in for a hug instead. I’m a hugger.

“Oh, look how handsome you are!” I said. “This is a nice surprise. Not that your photos weren’t good, but you know.”

Just the Tip Mid-Story Takeaway:

So many people on dating sites/app post misleading photos! Knock it off!

Back to the 50 First Dates Story…

It was too dark to see if he blushed, but he looked down and away while trying to refrain from smiling at the unexpected compliment.

I quickly learned this was his auto response to compliments, which was endearing.

Humble: Check.

After the host took us to our table, I slid into the booth seat (facing the venue) while he sat in the chair opposite me (with his back to the venue).

Seating arrangements are significant. Details to follow.

Meanwhile, the chair he sat on sank under his weight and then sat with his head level much below mine.

“Let’s switch sides,” I offered and he accepted.

Both our actions are significant. Details soon, I promise.

I’ll skip the specifics—we were together three hours—but will point out the important stuff that you care about—or should if you want to be successful in love.

I had one glass of wine. He had three beers. (Three hours, remember.)

We shared a charcuterie (fancy name for: cheeses, meats and accompaniments). We chatted.

He told me “his story” (sorry, confidential), but it wasn’t unlike many I’d heard, maybe even yours, including “looking for the right one.” (Significant.)

“My story” included how I’d taken a relationship sabbatical but was ready to date again, though with a disclaimer: “The next guy to bed this gal, weds this gal—I’m not interested in casual sex.” (This gets a hesitant chuckle and a raised eyebrow.)

I changed topic: “What would you do if you won $10,000,000?” (Significant.)

He replied immediately, snapping his fingers for emphasis: “I’d quit my job and travel.” (I raised my eyebrow.)

At the finish of the evening, he offered to walk me home, but I declined—significant—so we hugged and I told him I had a good time and would like to see him again.

Which was my bad. Why? Because … I regretted it as soon as I said it.

I did enjoy his company, but.


I did not want to kiss him, and he was my first real fake date, after all.

I had another 49 fellas to date, and at that time, I was willing to set aside exactly three hours a week for a Plus One.

Most men that are looking for long-term love want a bit more than a few hours a week with a “no texting—I loathe texting” condition attached, and since I’m not casual sex gal … well, I shouldn’t have said I’d like to see him again.

(Even though I was following my own dating rule: Don’t write off Mr. Potential Right just because you don’t want to get naked with him immediately.)

Significant 1st of 50 First Dates Takeaways:

  • Genuine modesty is attractive.
  • A woman feels more secure facing the crowd and men have fewer distractions (hot-ass servers, sports TVs, etc).
    • However, when the man is “below” her—physically—it takes away from his masculine confidence, in both the woman’s and man’s perceptions. Swap seats.
  • Booze: keep a level head.
    • Intoxication is not sexy. First impressions!
    • Ok, if you’re a (motor)biker, rocker or … nope, that’s it. If you’re a biker or rocker, drink whatever the F you want. But don’t get shit-hammered. Still not attractive.

Fellas: even though one per hour is within the legal limit for a lot of guys (people), best keep it to two to three maximum over the entire date. Maximum! Yes, you’re nervous. So is she. Deal with it. Sober.

  • If a gal tells you right off that her “clam” isn’t open for business without a commitment, believe her.
    • If you’re looking to settle down without settling you want a woman with respectable standards.
  • The 10 mil question is a classy way of finding out if the man must work and/or enjoys his work.
    • Relevance: If he hates his work, why’s he still doing it? Fear? Security? Lack of options? Lack of creativity? etc
    • The answer says a million different things about the person. Try it, you’ll see.
  • Walking (or driving) a gal home is a gentle way to tell if she wants more of your company and can be a signal from her as to whether or not you should attempt to kiss her.
    • As noted in my last blog, it’s ok to not kiss on the first date.
    • If there’s mutual interest, her lips will be there next time.
    • If not, you haven’t shared spit with a stranger.

In Summary

You may need to go on 50 first dates or 100. I ain’t gonna fib, online dating is work.

Online dating is like dumpster diving for diamonds. If you’re diligent, you might discover a gem amongst the rubbish.

In my next 50 First Dates update, I’ll let y’all in on my second first date with Slouching Stargazer.

Stay tuned!

xo AJ

In the meantime, consider my WakeUP2Luv program, it’ll help you become the kind of man who naturally wins the respect of women, peers and most importantly – himself.

Or start with the basics of online dating with my uber affordable Double Your Online Dating training.


Double Your Online Dating program
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Initiate Touch on a 1st Date
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When to Kiss Her

Since my $10 million question maybe made you wonder if all women are money grubbing gold diggers…

Here’s a short playlist on understanding women’s nature aka #hypergamy to consider: