My Husband’s Playbook: How to Plan a Great First Date

Kat and Dan on a Hiking Date

My lovely husband is a lot of things: spontaneous, good-humoured, intelligent, fun, adventurous, a real treat for the eyes, the list goes on. One thing he is not especially great at is organization. He operates according to a map in his head that keeps updating, which is always confusing for someone unable to read his mind.

The reason I bring this up is that Dan was uncharacteristically organized for our first few dates. They were well thought out, he followed up to confirm, and he picked me up on time.

There were no vague texts, radio silence, or presumption. When you’re tired of dating losers, a man with a plan is ultra-refreshing.

If you’re trying to figure out an awesome first date, do as Dan did.

Here are some reasons our first date went so well:

Make Plans Days in Advance

Nothing bums me out more than hearing about somebody waiting to get a last-minute text to go out. People of the world: you deserve better than a last-minute invite. We all know that means that you’re ranking pretty low as a priority. 

The only time a last-minute plan is okay is when impulse strikes and you and your beloved (or beliked) are off on a whirlwind adventure. I’m not sure beliked is a word, but you get what I mean. 

In the get-to-know each other phase of our relationship before our first date, Dan and I had many phone calls. Yes. Phone calls. It’s where you dial somebody’s number and speak to them directly in real-time. Insane in today’s world, no? I found this very endearing and ate it up.

It’s great to get a text message, voice message, or email from somebody you’re fond of, but having an actual conversation–especially a good conversation–is the absolute tops for me.

Before we went out on our first date, Dan and I spent hours chatting on the phone getting to know each other. I mean, getting familiar beyond our first impressions from the barbecue where we met.

Be bold. Make a phone call.

Leave a Little Mystery

Dan wanted to figure out what to do on our date but he wanted it to be a solo mission. That’s cool. His plan for the night tells me more about who he is based on what he wants to do.

Once we decided on when to get together, he said, “I’ll come up with something fun to do and text you the details.”

Texting details is key. What’s worse than getting the date or time wrong because your ol’ noggin remembers incorrectly or your ol’ ears don’t listen properly? Get it in writing.

The day before our first date, I received a text from Dan, “Activewear is required. I’m not giving any hints about what we’re doing.”

I loved this. Clearly, his background in marketing was at work, because I was thrilled, intrigued, and whatever he was selling, I was buying it. There are so many things that we could do in activewear. As long as it’s not running a marathon, we’re good (I’m still trying to convince myself that I enjoy running…we’re not there yet).

This message showed a few things about who Dan is as a person. He didn’t pick a generic first date like dinner or coffee. He knows that I like to move, so he planned an activity where we could make a memory together. 

Don’t Ruin the Surprise, Kat

I couldn’t leave it alone. I’m nosy by nature–I like to think I’m not nosy in a bad way, but what do I know? I’m a buffoon.

After I got Dan’s text about attire, I racked my brain thinking about what we could possibly do. Old habits. I can’t help it.

My brain raced as I mentally dissected our conversations about activities that we may have discussed. This was some of my finest detective work. Based on the evidence, I came up with two thoughts: a parkour gym or a trampoline park. I can’t tell you precisely what led to these possibilities, but it’s where I arrived.

“Are we going to a trampoline park?” I furiously text through my phone.

It took seconds to get a response. “How did you know that?”

Bingo. Oh self, you could have done really well as a crime investigator…if only you weren’t skeeved out by gross stuff.

Offer to Pick Up Your Date

I only give this advice if you feel comfortable. Since Dan was a friend of a friend of mine, I was fine letting him pick me up from my place. If he was some internet weirdo it would definitely have been a meet in a public place type of situation.

I also dislike being the first person to arrive when you agree to meet up somewhere. Waiting isn’t my strong suit. 

Besides, getting picked up has perks.

If your date acts like a gentleman or gentlewoman and opens the car door, there are extra points right there. This is a two-way street–you need to hold doors open sometimes too. All’s fair, right? I don’t care who you are, everyone likes to be treated well. It’s a super sweet move that says all the right things. 

Dan kicked off our first date by holding a door open for me and years later he still does this. Yes, my husband is a catch with old school charm (with some things). I like him heaps.

Also by picking up your date, it breaks the ice. You get some time to familiarize yourself with the other person’s energy rather than figure it out at the same time you’re doing an activity.

The trampoline park was a 45-minute drive from my place. Dan and I had a great time swapping stories and making each other laugh on the drive. We weren’t competing with loud music or getting distracted by other people, we were able to just chill and be nerds in a car. Happy times.

An Active First Date is a Memorable First Date

Not to sound like a floozy (yes, I use words like floozy), but I can’t recall much of any first dates that consisted of just dinner. Or a movie. Or getting a drink. I know they happened, but they didn’t leave much of an impression.

Movement leaves an imprint on your memory. You’ll be able to recall how you felt doing something better than how you felt eating a starter salad. Tell me I’m wrong. 

Feel free to steal Dan’s idea and go to a trampoline park. It was a brilliant first date. I hadn’t been on a trampoline in years and we killed some calories by having childish fun. Highlights included tandem flips into the foam pit, double-bouncing each other like children, slam-dunking basketballs, and racing across the small trampolines to see who was fastest (I was not…).

I have a mind like a sieve when it comes to some things, but this night is locked in the ol’ memory bank.

Leave Some Time to be Impulsive

I love a person with a plan, but not everything needs to be scheduled.

After the trampoline park, Dan drove to a park by the airport. We sat on statues made to look like paper planes and wandered down a path that looked like an airport runway. I’ve never been there before (mostly because I didn’t know it existed).

While we were there, many planes flew overhead and they were so close they looked enormous. When you usually see them, planes fly across the sky looking like small insects in your line of vision. This was a different experience for me and now anytime I go near that park I think of dear old Dan.

The park was not an intended part of the evening, but Dan slyly wanted to extend our time together. I also would have settled for ice cream, but seeing something new was a delight.

Don’t Rush the First Kiss

I don’t know about you, but when a person rushes in for a kiss too early into a first date, I’m a little repulsed. Dude, get to know me first (along with the word floozy, I also use the word dude).

Dan didn’t kiss me until well after our time at the trampoline park. We were outside, the stars were out, planes flew overhead, you could hear the cars whizzing past in the background. Not the location where I expected a first kiss, but sometimes there are some things you can’t plan. 

Also, if you’re actually PLANNING the first kiss, you should know that it’s weird. Don’t do it.

Make Plans for Your Next Date

If you truly had a good time on your date, pre-emptively make plans to see each other again. This whole ‘wait three days to call’ situation is stupid. I don’t know why it’s a thing.

If you like somebody. Tell them. If you’re not feeling the spark, don’t lead them on. Super simple stuff, guys.

If you have intentions to see somebody again, tell them. Get something planned for your next date. Remember, there are plenty of people in the world, so if you don’t express your interest, the other person may move on.

A simple, “Can I see you again?” Goes a long way. If the answer is yes, set something up! Why wait? It’s a telltale sign that they’re not super interested if they don’t immediately want to make a plan.

Although…don’t go overboard and try to schedule yourself into the person’s every waking minute. That’ s red flag territory. Stay out of that territory. It’s not a good look.

I love first dates. Well, no. Let me clarify since I’m a married woman and I haven’t had a first date since I met Dan: I love first date stories. There’s something so great about them: the energy, the anticipation, the creativity that some people exhibit.

Think a little outside the box and find some fun things to do with someone you like.

Here’s my thought about going to a restaurant for a first date: you need to eat. You’re inviting someone along to do something you’d be doing anyway. That’s not exactly charged with romance. This is ideal for some people, but not me. I need more.

My idea of a great first date is inviting someone to try something new with you. Or creating an experience that involves doing something fun like the driving range, going for a hike, taking a cooking class, shooting some hoops, the possibilities are endless.

You only get one first date, friends. What’s the story you want to tell people when they ask how you met?

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