Our 5 Best Dates of All Time and How to Recreate Them Yourself

Our 5 Best Dates of All Time and How to Recreate Them Yourself: from a couple who has been on thousands of dates and loves creative date ideas

We’ve been at this go-on-one-date-every-week-no-matter-what little project of ours for 7 years (whoa!), and we’ve been so lucky to have done a lot of incredible things!

Every time we have a truly incredible date we always discuss if it made the top 5 list, which we’re pretty stingy about new inductions into that club.

We love having this conversation and reflecting on our top dates, it brings up so many fun memories every time we go down that road. I really love that it’s so hard to choose but that there are several that are just clear winners as the best dates we’ve ever been on and our absolute favorites. I really love that we have them all ready to share with details and pictures and all the information you’ll need on how to recreate them yourself.

So want in on our current list of our best dates of all time? I’m so excited to share the Whiting favorites in no particular order because some are a little more favorite for me, some a little more favorite for Jacob. But we both agree, these are tops in our books! 

  1. Indoor Skydiving. There’s nothing quite like an adrenaline rush to get the endorphins going and let your body have the serious chemical rush that helps you feel in love! Indoor skydiving is one of those dates you won’t forget, and one of the best endorphin surges out there! It’s fun, it’s memorable, it’s in a safe environment, there are different levels of intensity for thrill seekers of all levels, and it’s the date that earned me the “Coolest Wife Award” after planning and surprising my husband with it. This is one of our more recent dates, and we both agreed quickly that it deserved to be on the top 5 list beating some other favorites out. There’s an arena in most major cities, so definitely look into the closest one near you, it’s worth every penny!

    Our 5 Best Dates of All Time and How to Recreate Them Yourself

  2. Attending The Lantern Fest. It’s hard to fully describe this event, but it honestly made us feel things we’ve never felt before by experiencing something we’ve never experienced anything like! It’s exciting, it’s romantic, it’s awe-inspiring. As you recreate the scenes from Disney’s Tangled lantern lighting night, you create this really amazing memory and experience. It’s amazing what a little fire, a biodegradable lantern, and a thousand other people doing the exact same thing at the same time to inspiring music can do for a date! I can’t even wait until it comes back again this year so we can experience it again! We shared all the details and a similar light festival links in this Lantern Fest date post.
  3. Recreating Starry Night. This was a date we found on Groupon (affiliate), and we were a little skeptical of but thought it may be fun to try something new. Neither of us is an artist, and it sounded a little out of our league so we went into this with very low expectations. But, we found very quickly that the BYOB painting classes are even more fun the less art experience you have. An instructor walks you through everything, it’s a real party with food, drinks, and music, and it’s something we both couldn’t stop talking about. I love adding this to any recommendation list because there are studios in almost every city and it’s just one of those dates every single person seems to enjoy immensely.
  4. Seeing Hamilton. This was a grand surprise that I’m still amazed Jacob pulled off! But this is one idea that applies even if you’re not a Hamilton fan. The concept is the same, find something at least one of you is a major fangirl/fanboy of, it could be a concert, a play, a touring author, etc. Snag those tickets and surprise your significant other with them. My jaw dropped the day Jacob called me from a business trip in the middle of the day with some really exciting surprise news. No, he wasn’t pregnant, but he made sure we got to be in “the room where it happened” and see the musical we’d both been obsessing about for almost a year! We shared how he got tickets in our Hamilton date post.

    Our 5 Best Dates of All Time and How to Recreate Them Yourself

  5. Romantic Paddle Boats. What I thought may be a somewhat enjoyable activity turned into a night I’ll never forget! We picked up an easy fast-food picnic, we hit the lake in the center of our city as dusk, and we paddled while we watched the sun set one perfect spring evening. We had some of the best conversations, we had endorphins flowing (thanks, minor exercise), and we watched some of the most breathtaking views of sunsets and city lights. I kept thinking how it may have been the most romantic date we’ve ever had, and we both commented how we feel a little more in love that night. Find everything romantic paddle boat dating here.

We’ll continue to look for the most fun, original, and romantic date ideas we can find, but so far that’s our list and most have stuck around for a long time! But don’t worry, I’ll come back and add an addendum if anything should change and ear the title of one of our best dates of all time!

We’d love to hear, do you have an all-time favorite date that you’ve been on? Let us know so others can continue to enjoy the wealth and continue to plan the best dates of all time!

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