Skylar is a Texas-based wedding planner & designer sharing her sanity-saving processes & templates.


How I Date My Partner

After over a decade together, including five years of marriage, you would think we’d have dating each other all figured out. However, like many couples, work, routines, and the demands of life had made date nights a nearly non-existent celebration in our home.

Determined to change this, we embarked on a mission to plan 24 special date nights for the 2023 calendar year. In this post, I’ll share our journey of creating and implementing these date nights, allowing us to intentionally connect and nurture our relationship.

The Date Night Draft

While I’ve been referring to it as “The Date Night Draft,” I’m fully aware that sports aficionados are running to my comments to contest this. Like all good millennials, I picked up this idea from a (un-saved, oops!) TikTok I saw in late 2022.

The concept was simple: write down date night ideas on sticks and randomly select one to determine our activity for the evening.

However, as a planner by nature, I knew that relying on spontaneous choices on the day of the date might result in us opting out due to a case of the “I-don’t-wannas”. To ensure we followed through, we decided to have a “draft night” instead, where we would collectively schedule and loosely plan our dates.

Inside Dates & Outside Dates

Another TikTok-inspired idea provided us with a framework for our date nights.

In a video, a young couple shared their budget-friendly approach to dating: alternating between “inside” dates and “outside” dates. Inside dates were designed to be low-cost and enjoyed at home (think cozy movie nights on the couch), while outside dates allowed for a bit more indulgence (such as dining out and catching a movie at the theater).

Although we’ve surpassed the days of tightly rationing our spending on dates, we loved the idea of balancing simpler, intimate experiences with occasional splurges, ensuring a variety of experiences as a couple.

Putting it on the Calendar

As a self-proclaimed “if-it’s-not-on-the-calendar-it-isn’t-happening” kind of person, I knew the importance of scheduling our date nights. I also understood my tendency to get carried away with exciting ideas but sometimes falter in execution.

Therefore, we sat down at the beginning of the year, armed with our calendar, and worked with my quirks instead of against them. Drawing date ideas from our designated bowl, we assigned activities to each month.

Skylar & Matt’s 2023 Date Night Plan

Here’s a sneak peek into our carefully crafted date night plan:

  • January
    • Breakfast for Dinner with a Childhood Movie (Inside)
    • Happy Hour (Outside)
  • February
    • ‘Italian Job’ and Italian Food (Inside)
    • Bowling (Outside)
  • March
    • Nostalgia Movie Night (Inside)
    • Local Art Installation Museum (Outside)
  • April
  • May
  • June
    • Private *cough cough* Photoshoot (Inside)
    • Ice Cream Date (Outside)
  • July
    • Painting with Bob Ross (Inside)
    • Local Museum and Dinner (Outside)
  • August
    • Spa Night (Inside)
    • Dinner at the Movies (Outside)
  • September
    • Bake Bread for Charcuterie Board (Inside)
    • Indoor Go-Karting (Outside)
  • October
    • Spa Night (Inside)
    • Bowling (Outside)
  • November
    • Puzzle (Inside)
    • Color Factory (Outside)
  • December
    • Rom-Com and Puzzle (Inside)
    • Coffee and Cards (Outside)

How It’s Going

Implementing this strategy has been a resounding success for us. We review and adjust the calendar at the end of each month to align with our schedule. Surprisingly, the dates we chose were well-spaced, and I’m hopeful the duplicates turn out to be unique experiences.

Of course, we’ve had a couple of missed date nights out of the ten opportunities we’ve so far, but we’ve learned to prioritize progress over perfection. Some of our most memorable date nights have happened when we pushed through, even if we weren’t initially in the mood. We’ve enjoyed the opportunity to create these date nights together, sharing the mental load of planning and ensuring a well-rounded mix of activities that cater to our individual interests and our connection as a couple.

As we journey through life and grow as individuals, it’s equally important to nurture our relationship by carving out time for one another, regardless of the season we find ourselves in. Our date night draft has allowed us to prioritize our relationship and create unforgettable memories together.

I hope this glimpse into our journey inspires you to make intentional efforts to date your partner and foster a deeper connection. Remember, it’s not about perfection but the progress you make as a couple. Cheers to many more date nights filled with love, laughter, and endless possibilities!

© 2018 showit template BY WITH GRACE AND GOLD.

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Photography by Smith House Weddings