October 16, 2018

I have an account on Instagram where I post dating messages. Sometimes they’re ones I’ve received myself, sometimes friends’ messages, clients’ messages, or messages submitted to me by other users of Instagram. The common theme of these messages is that each one highlights something—usually a problem to be fixed—and asks people who follow my account to comment on what I post.

A couple weeks ago, I posted this exchange below from the dating app Bumble, with my comment below it. The conversation picks up where the gentleman asked her what days worked to meet for a drink after work.

Her: Friday happy hour works! (I’m seeing a show at 8.)

Him: Happy hour Friday is perfect! What area do you need to be at 8? I will find a place convenient for where you need to be. Want to plan for 5:30/6?

Her: Perfecto! Let’s do 6 pm. And the show is at [insert location].

Him: Plenty of options around there. Want to meet at [insert bar]?

Her: That’s perfect! Looking forward to it. I also appreciate your taking the initiative in planning. 🙂

Him: Great! Looking forward to it as well. No problem on the planning, it’s my pleasure.

Him (a day before): Good morning! Just wanted to say hello. Looking forward to tomorrow. Have a great end of the week.

Her: Confirmed! Looking forward to it, too. Happy TGIF eve. 🙂

I then wrote to my Instagram followers this: “Take some notes… this is the proper way to arrange a date. He’s decisive, chivalrous, and responsible. Most women (and men) appreciate all of these qualities, especially the ‘confident confirmation’ vs. the weak ‘Are we still on?’ that many do. So many people struggle between asking someone out and then making the actual date happen. (And many clients complain about someone dropping the ball.) Follow this person’s lead to have a much better conversion rate.”

This post got comments from women like, “OMG, THIS IS A HUSBAND RIGHT HERE!” and “I would date him based on that conversation alone.” All it takes is some good ol’ planning. Nothing more, nothing less.

Now, let’s compare that conversation to one a female client received that same day:

Him: Was [asking you out] too forward?

Her: Not at all! Was just looking at my schedule actually. 🙂 I could do next Wednesday or Thursday. Either work for you?

Him: Let’s shoot for Wednesday. Shoot me a text and we’ll play it by ear. [Inserted his number]

Her: Wednesday it is. How’s 6:00? Let me know if you have a favorite place to meet. (I’d actually rather just make the plans on here if that’s okay… keeps me organized.) And since I have a daughter, I’m more of a “write in stone” than play by ear type. Cool?

The comments people wrote for this one included, “People today don’t write anything in stone and flake out too easily because of texting,” and “Play it by ear means ‘We’ll see if something better comes along.’”

Both men wanted dates. Both men asked. Both women said yes. Then things diverged. Bachelor #1 stepped it up, committing to plans and maturely scheduling them. Bachelor #2 is slowly losing his chance at getting to the date simply because he’s hedging his bets. Both men are in their 30s. Both live in major US cities. The difference? Commitment, maturity, and follow-through. Those things? Apparently “husband material.”


This is How to Properly Plan a Date

4 thoughts on “This is How to Properly Plan a Date

  • December 27, 2018 at 4:55 am

    If people that write articles cared more about writing great material like you, more readers would read their content. It’s refreshing to find such original content in an otherwise copy-cat world. Thank you so much.
    Visit us: http://lovedatingout.com/

  • February 8, 2019 at 4:16 am

    Could it be that the guy in the first example was just way more interested in the woman, than the guy in the second example?

    • February 20, 2019 at 12:33 am

      While that is a definite possibility, there’s also an element of maturity there, too.

      • April 15, 2019 at 8:07 pm

        It’s not so much maturity as taking charge (while giving the woman the opportunity to change details if she wants to).


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