A Memorable First Date

Dear Justin, I want to ask this girl out, and while I’m confident about asking her out, I have no idea how to ensure that the first date goes well. I want to make sure it doesn’t descend into awkwardness, and is actually productive. Can you give me some pointers on making a great first date? –Pete in Dayton

Firstly, hi folks! I’m back after being on a month-long hiatus. A few of you have sent me some questions that I haven’t touched on, so, if you don’t hear from me in the coming week—send me another email. I’ll respond to you personally if not in next week’s column.

I love first dates, Pete.

Congrats on being confident that she’s going to accept your date request. The majority of folks that ask me for advice aren’t nearly that confident. First dates aren’t rocket science, but the old clichés of dinner or a movie, or both, aren’t necessarily the best options. I’ll touch on why it’s not the best option in a bit. The biggest thing is, don’t stress. If you’re having fun, she’ll have fun!

Now, the old standbys have some major flaws. A movie, for example, doesn’t allow you any opportunity to talk to each other. It’s a pretty weak first date if you don’t have the opportunity to learn about your date and tell her a bit about yourself! A classic dinner date is a little cliché, and again, a crowded restaurant isn’t the best place to build intimacy. So what are the alternatives? Well, there are plenty! The route to go with depends on what your goal for the evening is.

Allow me to elaborate…

In my younger days, I was much less of a reformed playboy, and much more of an actual playboy. My classic first date move was simple:

  1. Schedule a very non-threatening date, such as lunch, or early afternoon coffee.
  2. Call her the morning of and say something came up
  3. Ask to reschedule for drinks later that night (as late as you can get away with)
  4. Have drinks, be amazing, bring her home.
  5. Repeat every time you meet a new girl, ad infinitum.

Now, I’ll be the first to admit that my intentions in using this move weren’t exactly to find a girlfriend or future wife. I’m sure you can imagine what I was going for, and frankly it was incredibly affective. The problem is, it’s also really douchey, and a little bit manipulative.

When you actually like a girl, there are much, much, better first dates that will allow you to have fun and build a real connection while also getting to know her better. Here are three of my favourites:

    • A picnic in the park that consisted of appetizers, champagne, and a Frisbee.
    • An evening stroll through the market in Ottawa with smoothies that ended at Major’s Hill Park (best view in the city).
    • Minigolfing, particularly if they serve drinks! Make sure to make it fun, and not uber competitive though!

Basically, the trick to putting together a fun first date is combining something you would enjoy doing anyway, with something that has a touch of romantic in it. Adding a picnic to a Frisbee is the perfect combination. You can go with the old standards of just drinks or dinner or something, if you’re more comfortable with that, but you should know in advance that you’ll be just like every other schmuck that’s ever asked her out. Try to be a little more memorable!

PS: If you’re ever in London, Ontario, there’s a beautiful spot on the roof of the city place that you can only access by going through one of the theatres at Rainbow Cinema. True story.


Justin Samlal is a reformed playboy, and is now blissfully engaged. He has been dubbed a master of social psychology by his peers, and has a wealth of experience in the dating scene. Justin is now Landmark Report's resident relationship guru, and is here to answer your questions! Please send them to: Letters@LandmarkReport.com.

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2 Responses to “A Memorable First Date”

  1. Denycom says:

    Picnic is always a great idea whether it’s your first or 1001st date!

  2. Brendan says:

    First date with Hope, took her to the ROM, then hot dogs from a street vendor, then drinks at my place. Epic

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