How to plan a surprise date night

1. Getting the timing right

Timing is incredibly important for a date night and that goes double when it’s supposed to be a surprise. Even if you nail absolutely everything else on this list, it’ll all be wasted if your partner simply doesn’t have the mental space or the time to enjoy it properly.

Here’s a few key points to keep in mind for timing your surprise date night.

• Dont double book. Always double and triple check that you absolutely, 100%, do not have something else on for that slot. And check again closer to the time to ensure that your partner hasn’t made plans without mentioning it to you.
• Try to avoid busy days. Long meetings and major events throughout the day can be very draining. You might find that if you try to head out on a surprise date night on a weekday evening, your partner will simply be too tired to enjoy it properly. Avoid busy days completely if you can.
• Consider what’s happening afterwards. There’s nothing that kills a date night vibe more than knowing that you have to Do Something Important afterwards. Just like avoiding a busy day, try to avoid planning a surprise for a time when your partner has a commitment afterwards as well. Otherwise, they might spend more time thinking about that than the awesome surprise you’ve planned.

Timing is one of the reasons why we designed Cupla as a shared calendar app! Sure, we provide tips, tricks and suggestions for date nights too, but if you don’t have the right timing with your partner, that’s all moot. 

2. Getting the activity right

When you’re planning a date night that you’ll both enjoy, communication with your partner is key. But when the date night is supposed to be a surprise, it’s not as easy as clearing the date with your partner first – all that will do is spoil it.

Don’t fret! There are ways around this. Our suggestion is to plan your date night activities well ahead of time with your partner. Often, the whole point of a surprise date night isn’t the activity itself, but rather the timing of it. If you’ve already decided that, say, dinner and a movie is something you’d both enjoy, all you have to do is get the timing right and you’re golden.

On that note, don’t be fooled into thinking that a date night has to be some enormous, creative, and incredible event. It certainly can be, and don’t let us clip your creative wings, but again: the surprise is often in the timing, not the activity. Sticking with something you know you and your partner will both enjoy will be just as successful.

Related: Planning Date Night: The Busy Person’s Guide

3. Plan and book ahead

Ironically, lots of planning goes into spontaneity. Booking your surprise activities well ahead of time is absolutely mandatory. Nothing kills the vibe more than rolling up to the location and being turned away because the restaurant is full or the activity is at capacity.

It’s also a good idea to pick a couple of different activities. Variety is the spice of life after all, and if, somehow, something does go awry for the evening, a secondary activity will ensure the date keeps going and your effort – and the surprise – isn’t wasted.

Looking for a few ideas of what to do? Cupla has a bunch of awesome suggestions for date nights, surprise or otherwise.

4. Get friends/family involved

We get it. Planning a surprise date night is a lot of work. So don’t be afraid to ask for help from friends and family. In fact, getting them involved can make your surprise date night feel even more special!

This can range from something simple like babysitting on the night (without running the risk of a hired babysitter showing up early and spoiling the surprise) to something more devious like dropping your partner off to your secret date location without spilling the beans.

You’ll find that friends and family are often more than willing to help out, and it’ll free you up to concentrate on making your surprise date night truly memorable.