Progressive Date Couple dancing, couple in the mountains, couple sitting down with a dark

Progressive Date

First I want to point out that the word “progressive” here does not refer to anything political. It is a group date that builds upon itself. The progressive date follows a similar format as the progressive dinner, except that instead of restaurants, you’ll pick activities out of a hat. The actual dates themselves don’t necessarily have to be creative, but the very act of putting them in the hat makes it a fun and exciting event, and somewhat of a mystery. Some ideas you can put in the hat are mini-golfing, indoor rock climbing, video games, or bowling, among many other things.

Of course, you could let your creativity flow and have every idea be some wildly creative activity. That would take a lot of planning and the problem is you may not get to all the dates, or will you? It depends on what the activities are and how long your date winds up being. And just like the progressive dinner idea, you could write riddles that make the group guess what the activity is, or you could just be blunt and write what the activity is on the paper.

So to sum up this group date idea, you come up with a slew of fun activities that you think your group would enjoy doing throughout the day or evening. Then you write those ideas down on pieces of paper and put them in a bowl or hat. You plan out each activity in case they get picked. When your group gets together you have one of the couples or someone in the group picks out the first clue/activity. Then go and do that activity. After you are done have someone new pick a new clue/activity. You get the idea right?

What you need for this date: 

Just like the progressive dinner, all you need are some ideas and something to write them down on, as well as something to put them in. Be as fun and clever as you want with the clues. You will also need to prepare for the activities. Is one of your ideas going to the climbing gym? Make sure you know where it is if you need to call ahead, etc. Going bowling? Make sure there isn’t a league going on so you will actually be able to play if that activity gets picked. And so on. It never hurts to be prepared.  

My experience with this progressive date idea: 

One time, my friend Jack and I wanted to do a double date that was exciting, and something new we hadn’t done before. We wanted the girls to have a lot of fun as well, so I came up with the progressive date idea. 

We picked the girls up and explained to them the idea for the date. I don’t mean to brag, but they were really excited.  I even received a few compliments about how clever of an idea it was. That’s right, I’m not ashamed of how proud I am.

My date picked out the first thing to do, which was a sandwich place for dinner. The food was good, the company was good, and dang it, the flirting was good.

Dance Dance Revolution?

The next thing picked was the Dance Dance Revolution video game. It is an old game nowadays Just Dance would be the equivalent. We danced around, failing miserably to win even one of the rounds. I tried my best to have moves like Jagger. Gotta try and impress my date, you know? While waiting for our turns my date snuggled up close to me—definitely a good sign.  

Dollar Store Winner

After about an hour we had the girls pick the next idea out of the hat. The winning activity was called “Dollar Store Winner.”  Basically, you go to the Dollar Store and see who can find the coolest thing for a dollar. You don’t have to buy it, just have fun trying to find something better than the other couple. Lacey, my date, kept bumping into me “on accident” and grabbing my arm; I knew what was going through her mind. Another good sign, maybe I DID have moves like Jagger?

Dress Your Date

thrift store with lots of old clothes

The next activity was “Dress your Date.” This is where you have five dollars, the amount is really to you, for your date and the same amount for yourself, and you go to a place like Goodwill or Salvation Army, any thrift store, to buy the wildest clothes for your date to wear. The best part is that whatever you choose for them, they have to wear the rest of the night. My date dressed me up like an elderly woman. I had to wear a muumuu-type dress and walk around Walmart in it. Classic.

We had a lot of fun that night; I thought she liked me, she said she had tons of fun on the date, she had been laughing and smiling and flirty the whole time, but I was wrong. You guessed it—she didn’t want to go out again after that. Sigh. My experience with dating is kind of like “In the End” by Linkin Park: “I tried so hard and got so far, but in the end, it doesn’t even matter.” But, have no fear; being positive keeps me going, and in all actuality, I know that sometime down the road I’ll meet a really cool girl. Once the stars and planets align, we’ll live happily ever after . . .

Check out the video I made for the progressive date idea

Do you have experience with this creative date idea? Let me know in the comments how it went and if your date, spouse, significant other liked it. You can buy a copy of the book 101 Creative Dates: ideas, tips, and personal experiences from the life of a hopeless romantic here or visit the shop.

Here are other date and gift ideas you might like:

Kite Flying

Murder Mystery Dinner Party

Outdoor Movie