50 First Dates—First (Faux) Date #10: The Chatterbox

How to Approach a Girl on the Street

Meeting Place: On the street
Stats: Mid 40s, no kids
Work: Performing Arts

I was on my way to the grocery store. He walked by me going the opposite direction. I noticed him because he looks a lot like a fairly well-known actor, Michael Fassbender.

He might have mistaken my noticing him for interest because he about-faced and walked back to me to ask, “Do you happen to know the time?” He has an accent. Irish, it turns out.

I tell him, “It’s 4:35. Ish.” And laugh at the “ish” bit.

My laughing persuades him to walk alongside me and chat about the magic of the twinkling Christmas lights in the Yaletown trees.

I’m open and friendly, so he continues walking and chatting with me, occasionally asking me a question, but more so rambling on in an extended monologue of his life.

What we have learned so far—

  • An easy way to strike up a conversation is to ask someone what the time is. Asking for directions also works.

Example: “Do you know where the nearest Starbucks is?”

More effective: “Do you know where the nearest Starbucks is—or a good coffee shop?” (laugh)

Best: “I’m looking for a decent coffee shop. Do you happen to drink coffee and know where one is close by?”

Ultra smooth (but risky): “…If it’s in the direction you’re going, perhaps I could walk with you…” And then at the location where she points you in the right direction and if you’ve had an easy conversation thus far, you could ask to buy her a coffee or exchange contact information for a future decent coffee.

Back to the Faux Date story …

He walks me all the way to the grocery store. We chat outside for a bit—or rather, he continues his monologue.

Finally I say, “We need to get collard greens and spinach.” The “we” gives him permission to accompany me on my get-green-groceries excursion. He does.

Two and a half hours later, after much distraction and physical shenanigans consisting of him providing bits and pieces of theatrical performance—displaying different accents, sweeping hand gestures of Shakespearian romance with exaggerated declarations of devotion (to me)—I’ve got my greens and we (we!) are at the checkout.

I allow him to carry my grocery bag. All the way home. I’m in an easy-going mood and haven’t had to make conversation. (He’s done that all on his own.)

Too Much Talk + Exhaustive Humour = No 2nd Faux Date for You

At the front door to my building, I give him a hug and thank him for an entertaining evening. The message is clear—I am going into my building alone.

I don’t ask for his contact information or give him mine, though I do say, “You know enough about me to find me online.” I don’t say, “You should find me online” just “you can.”

What else we have learned—

  • If you talk too much for too long without feigning interest in your romantic interest, she’ll feel exhausted. Watch for the signs.
    Exiting stage left early is better than waiting for a third standing ovation when you didn’t even get a first. (In this case, my faux date did not leave me wanting more. In fact, he didn’t leave at all!)

Chatterbox Takeaways:

  1. Only show them enough to win―aka always leave them wanting more.
  2. All chuckles without some serious substance is great for stage comedy, but not street “meet & greets.”

By the way, ladies, other than the ultra-smooth move, we can also meet & greet in the street by asking for the time or directions! This is called “dropping the handkerchief,” as in: giving a guy permission to pursue.

xo AJ

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About the Author Anna Jorgensen

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

Leave a Comment:

2 comments
Ron Werner says December 17, 2016

Good story. I’ve met some women I’ve dated by simple comments and then talking. You never know who you’ll meet.
Enjoy your greens!

Reply
    Anna Jorgensen says December 17, 2016

    You’re right, Ron… The best approach is ANY approach!! 🙂

    Reply
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