Insights from Dana
Date Night Guidelines for Business Owners

When was the last time you went on a real date with the person you love?

As a business owner, date nights are haphazard, right? You’ll schedule date nights, and they’ll get canceled for one reason or another. Either you have to stay at work, nobody booked the babysitter, for so many reasons God only knows. And that’s so romantic. NOT!

As a high-strategy coach who guides business owners to step fully into their role as CEO, we focus on their personal lives as part of their growth into badass business leaders. So, I developed a specific set of guidelines around date nights. 

Number 1 is Set a Schedule.

Schedule a regular time for date night instead of haphazardly trying to fit in an evening out at the last minute. If you can manage once a week, that’s the best, although that just isn’t realistic for some folks. So every other week will work. Once a month is too few to keep your relationship going on a consistent basis, but it is better than nothing. 

Something to remember…. People say that relationships are hard work. The truth is, it’s not that it’s hard work, but it takes consciousness and intention. It takes thinking about it. It takes putting your energy into it. It takes effort. 

Do you have to have a date night? Of course not. But, if you’re not going to commit to spending quality time with your partner, what’s the point of being in a relationship?

So set a schedule!

Number 2 is Take Turns Planning.

This is the best thing! One of the things I really hate is having to make all the decisions, all the time. By the end of the day, let alone week, I’m so tired of making decisions. When you alternate planning and take turns owning date night, it isn’t always on one person to make it happen. You don’t have to make all the decisions, and you get to be surprised half the time. SO much fun!

When it’s your turn to plan the date, you decide the activity, plan all the logistics (including getting the babysitter if you need one), and the only thing your partner can ask about is how to dress. 

You don’t want them to show up in a cocktail dress or a suit If you’re going on a hike. That would be embarrassing, and it wouldn’t create the container for having a good time. Do not plan something you know your partner doesn’t like to do. That’s just not fair, and it’s not in the spirit of date night.

When planning date night, often the easy route is to think “dinner and movie.” This can be fun once in a great while, but it is not a good, ongoing solution. When watching a movie, you may be spending time together, but you’re not sharing yourselves with each other. Keep this plan in your pocket for times when you really can’t think of anything else to do. 

Remember, you don’t have to spend money when you’re on a date. Hell, you don’t even need to leave your house! During the pandemic, we’ve had picnics in the living room, game night on the porch, and of course, a walk by the river. You can be as frugal or as extravagant as you want, as long as you stay within the limits you have created together around date expenses.

Number 3 is Talking Topics

This is so important! Back at the beginning of your romance, when you were first dating, what kinds of conversations did you have? You bantered; you flirted; you got to know each other. You listened deeply, and gave each other space to think and respond. 

You didn’t talk about things that pushed each other’s buttons. 

You didn’t talk about money. 

You didn’t talk about your kids all the time. 

I’m not saying don’t talk about hard things, because, in retrospect, we talked about a lot of hard things in the beginning. Those hard conversations were born from a place of vulnerability and exploration, of sharing ourselves and discovering each other, not from a place of stress or tension. 

Don’t bring up trigger issues, unresolved arguments, those topics that you fight or bicker about. Date night is about rekindling your love, putting on your lover role, your infatuation hat, not an opportunity to dig at each other. 

Share yourself. Talk about something you’ve been thinking about, perhaps something new that happened, a funny story you heard, or just hold hands. 

I was watching a snippet of a TED talk on TikTok recently about how laughter increases the same hormones as falling in love does. Keep that in mind. The more you can laugh together, the closer you will feel to one another. 

Knowing that you’ll be ‘dating’ your honey again may inspire you to start a new project, or learn a new skill, so you’ll have something to talk about beyond the day-to-day, kids, business, etc. If you spend your entire time, week after week, talking about work, the kids, or the same old troubles, it’s not going to feel like a date. 

I’m not saying you should never talk about these things, but, to keep the spark alive, keep the mundane and hard topics for other times.

Number 4 is The Gratitude Moment

This one is a little mushy, but essential. On every date, take a moment to express your gratitude to your partner for something they did that week that you really appreciated, something that made you smile, or made your life easier in some way. One of the things that happens over a long-term relationship is that you take the people you love the most for granted. 

You forget to tell them how much you care and how important they are to you. 
If you want to go the extra mile, make gratitude moments a daily practice. Be grateful and express your love whenever your partner does something that makes life easier. It can seem silly to thank your partner for doing mundane tasks that have to be done on a daily basis, but it makes such a difference knowing they’re being seen and appreciated. When this is a habit for both of you, you will both feel so loved every day!

Number 5 is Have Fun!

It seems silly to have this here, but having fun is the most important ingredient! If you’re not having fun dating, why would you keep doing it?

Important caveat!

Going on date night never implies or creates an obligation to have sex. 

Date night is about being connected intimately, it’s not a bribe to get you in bed. 

The same rules apply as when you were just getting to know each other. I never want anybody to feel like because they’re scheduling, or planning, and having regular date nights with their partner, that it means they have to put out. 

You never “have to” have sex.

It can be fun when sex happens, but it isn’t a “requirement” – enthusiastic and ongoing consent IS.

Here are the Date Night Guidelines for Business Owners again:

  1. Set a Schedule – Every week or every other week
  1. Take Turns Planning – Surprise each other
  1. Conscious Talking Topics – Leave the mundane and triggers behind
  1. Gratitude Moment – Express your love and appreciation
  1. Have Fun!

I’ve told you mine, now you tell me yours. 

How do YOU do date night? 

Are there tips, tricks, or strategies that you have around date night that I haven’t mentioned? 

I’m always looking for ways to make this more fun!

It’s so easy as a business owner to lose touch with the people that matter most to us because we take them for granted. It’s easy to single-mindedly focus on building our businesses – so make sure you’re prioritizing spending time with the ones you love!

dana corey signature

Like it? Share it!


Are You an Overloaded CEO?

Which of the 5 Swamped Business Owner Syndromes is keeping you overly busy, stressed, and exhausted?

Take this personalized assessment to find your strategic next steps.