Design A Date (In 4 Simple Steps)

Dates are fun. They’re a way of getting to know someone in a less serious, (hopefully) comfortable environment, and, if done right, can provide some great memories whether the relationship lasts or not. Dates can also be awful. They can be awkward and forced, and leave both of you wondering why you didn’t spend your night at home with Netflix. The purpose of this article to is to make the good dates better, and the bad dates justifiable, because at the very least you did a hell of a job.

The title explains the intention: we’re going to design a date. We’re going to step outside of the conventions, and consciously step up our game on the classic dinner and a show by using it as our example. A brief mention. This article is targeted specifically at the male side of the date (see website title), but if you’re a woman, I think the principles of the article still apply. No guarantee, seeing as I’ve never been a woman of any kind, and aren’t too big on the idea of reincarnation, but regardless I hope you find something of value here.

The idea is simple: you eat dinner, then you go to a show. Dinner and a show. The term refers to Broadway, but any performance will do — I prefer live music, so we’re going to stick with that for the example. Now you could definitely have a decent time just picking a well-reviewed restaurant, seeing the popular movie, or going to see a good local band. All of that is a very respectable way of doing things, and obviously you want both of you to have fun and connect. But, that said, you could do a heck of a lot more with a little thought. So let’s do some scouting.


Part 1: Take inventory.

Stop for a minute and review the situation. You’ve been dating for 3 months, you live in or near a city (or a place with several buildings in a line), and you know that she likes music with interesting lyrics (she minored in literature in college), to try new things and spontaneity. A little hard to seem spontaneous when the title is “Design A Date”, right? No. It’s actually easier. But we’ll come to that.

So you know what she likes. Cool. You want to provide a really stellar experience, one that’s filled with those “moments” that she’ll talk with her friends about when she sees them this week. We’re going to use just those couple of bits about here to really kick it up a notch. Before that, however, I’ll offer the caveat there are undoubtedly bajillions of different things that interest different people, and these three by no means come close to the full range. But I figured that at least the latter two are somewhat common, and the first will give us a jumping off point for the night. Please find what works for you and do that. Now, moving on.


Part 2: Fire on all cylinders.

Keeping in mind her preferences, let’s begin. She enjoys thoughtful music. Think of the artists you know who fit that criteria and won’t obliterate your wallet. A guy I like a lot named Chris Smither meets these parameters, and if you don’t care about money, you could try someone like Bruce Springsteen. Even a street poetry reading can do. Whatever it is, make a decision and pick a day. We’re going to use Chris.

First like met. Now what about new things? Go to the food. Use Google Maps to find restaurants near the venue that are unusual. Ethiopian food? Maybe you didn’t even know that was its own thing (I didn’t). Either way, she probably didn’t grow up with every Friday being “Ethiopian night” (and if she did, sweet). So you’re trying new things, and already this date is taking steps towards being a little adventure.

Before we hit point three, we’re gonna use technology to our advantage. If you use Google Now on your phone, or the Google Maps recommended attractions feature, you’ll find that Google will tell you where there are cool views and photo spots near any given location. Wouldn’t it be a treat if, after the concert, you were able to stop by a view of the river/bay/mountains/coolest skyscraper/local monument? It’s up to you. But that kind of research pays dividends to the “wow” factor. This also meets another standard I think it’s worth mentioning — always keep at least one surprise. You can have a great night made spectacular with just a little surprise. Even something as simple as not telling her about the concert is workable.


Part 3:  Enjoy the work you put in.

Now we arrive at spontaneity. Again, it might seem counter-intuitive to advocate spontaneity in this piece, but it totally fits. When you’ve got a kick-ass night planned, you feel good. When you feel good, you’re confident. When you’re confident, she’s excited, and confident in you. She reflects you. Good vibes on both ends of a relationship can make for some pretty excellent “out of the blue” ideas. Not to mention that all the happy chemicals in your body are congratulating you on your ability to create something great for her, and they contribute the double whammy of telling your brain to be more ok with risks. Both of you feeling good, more ok with new things, and excited to be out together creates those kind of things usually reserved for Walt Disney’s imagination. Feeling solid in what you’ve done allows you to trust yourself to deviate from the plan, and enjoy what the environment’s offering you even more.


Part 4: Index.

In the interest of keeping this article a palatable length, I’ve glossed over a lot more of the minor details that I think bring a lot of quality to the moment-to-moment of a decent date. But I don’t want to leave them out. So this is a “variable index” —  a list of things that you have influence over and can make the time something really special. It’s just shorter to list than to write sentences about each. Take what you like, and leave what you don’t.

>> Music: what’s playing, and when.

>> The Route: find something special to see and walk/drive by.

>> The Menu: does she have a favorite food from her family, or a memory associated with a certain dish? Check out different menus to find it.

>> Memory Links: Esoteric title, I know. Think of something special in your relationship — maybe an animal that you only see together, or a flower type you gave her on her birthday. There are gardens and opportunities for this everywhere. I dated a girl who thought butterflies were just the bees knees (pun intended, sue me). We went out for a walk one time where I made sure we stopped at a lake with plenty of butterflies. It’s the little things.

>> Encounters of Value: another odd title. And another story. I dated a (separate) girl who was quite the pianist. We went into NYC for a day trip, and you can be damn sure we passed by where this one street pianist played (he was very good). I think we stood there for a good 20 minutes listening to him play — that was exciting for her. Think outside the box.

>> Mementos: If you go to a concert, or any venue that has paper with the company name on it (playbill, performance pamphlet, even a business card), keep it and make it a tangible reminder of the evening.

>> Research “Moments” Ahead of Time: If there’s a photo booth one block over from your charted course, give it a swing by and get connected in yet another way.

So let’s take summary of this date. You pick her up — and by the way, go up and ring the goddamn doorbell. Do not text people that you’re outside. Jesus. — with her favorite artist, or style, playing on the car radio (quietly). You go into town and pass through some gardens on the walk to the new type of restaurant. You try new food together, and walk it off by the water or through a historical part of town, before arriving at the thoughtful lyricist’s concert. You enjoy the music and go home, but not before slipping the show program into her purse, complete with something sweet to say. Now that is a next level date. You’ve just shown that you’re really engaged in making her happy, and she knows it. You’ve connected over new experiences, and you’ve got something to talk about into the future. Congratulations — you’ve just made a designer date.


rowan“Rowan Groth doesn’t write bios in the 3rd person. That said, I do edit videos, write articles, travel about, play a couple of instruments (plus singing), and write comedy. Building computers and introspecting go in there too. Late night conversations and good tea are my favorite things.”

Article image by Ashley Blagg Photography 


Please share this article with your friends because they may want to go on great dates too!


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