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5 Tips on How to Book Now & Tell (Your Significant Other) Later

Should you book your trip first and then deal with your significant other’s objections?

Here are some tips on how to handle a partner who needs convincing to go ahead and take that much-needed vacation.

I used to get frustrated trying to book a trip for me and my husband. He is the type of person who hates people, lines, waiting, and the chaos of traveling. He needs a lot of convincing and begging. Don’t get me wrong, he enjoys vacation when we actually get to our destination, but he hates the process of getting there. Both the planning and the booking of our vacations have always been my responsibility. The truth is, I enjoy doing the research and looking for the best deals.

My husband wouldn’t even know where to start (or want the pressure of making sure it all “falls into place”). We have been together for more than 20 years, and I’ve adopted the approach of “book now, tell him later.” I do this probably around 5 times a year (for both family trips and quick romantic getaways).

Here are my 5 tips on how to do this while (hopefully) keeping your relationship intact.

#1 – Always check the cancellation policy

Since the start of the pandemic, the travel industry has been forced to adjust their cancellation policies to be more accommodating and accepting of last-minute cancellations. In doing so, many travel companies from airlines to hotels and cruise lines have waived cancellation fees all together, or at least offered a credit for future use. For me, this was huge! As we all get back to travel, we need that level of comfort in knowing that if our plans had to change, that we would not be subject to crazy cancellation penalties. Just be sure to read the full terms and conditions. Sometimes, you may have to pay a little more for refundable options, which may be worth it in some cases. Nothing annoys me more than getting zapped with a “one-night’s cost” of a cancellation fee. You could be out several hundred dollars in many cases, and that’s money that you could spend on experiences or food during your actual vacation. Plus, when you go to tell your significant other that you already booked something, it’s imperative that you can fall back on the fact that it can totally be cancelled without penalty if you need to change it. 😉

#2 – Look for early booking deals

Many hotels and travel companies offer discounts if you book early, and if these deals are combined with no cancellation fees, it’s worth booking the deal as soon as you see it. Be sure to do your research. I like to use sites like and Expedia, who clearly list the cancellation penalty and early booking discounts.

Plus, we all need something to look forward to… a light at the end of the tunnel and motivation to help you get through the next few weeks or months.

I recently booked a hotel and airfare to Key West for our anniversary. It was compulsive. I did not want to miss out on the deal and had to act fast! I was able to book the hotel and not pay anything now (full payment wasn’t due until check-in). I can cancel up until 5 days before check-in without any penalty. I did have to provide a credit card, but it will not be charged. Then I went to book my airfare. I had a previous air credit from a trip that was cancelled back at the beginning of the pandemic. I applied that to my flight and had a small difference to pay. To this point, I booked a vacation and only had to pay $23 for each of us. My airfare was protected such that if I had to cancel, I’d get another flight credit for future use. In my head, I would not be losing any money on this venture. It’s a win!

#3 – Set a reminder a few days before the last day it can be cancelled

Once you go ahead and book something (or maybe you even booked multiple options), be sure that you set a reminder on your calendar or your phone a few days in advance of the last date you have to cancel without penalty. There’s nothing worse than getting ready for your trip only to realize you forgot to cancel that other hotel you booked months ago just to have a backup. This will also create a deadline for you to speak with your significant other and get their buy-in on the trip ahead of time.

If either (or both) of you need to request time off from work, it’s also a good idea to know that deadline and set a reminder for that too.

#4 – Pre-plan the logistics

Now that your trip is booked, it’s time to think of all the logistics that also need to be handled ahead of time. The more prepared I am, the less objections (and stress) my husband will have in advance of the trip. First things first, for this Key West getaway I am planning, I need to find childcare. Luckily, I have grandparents close by who are willing and able to help.

I also have neighbors and friends willing to step in if needed and help with the kids. You may have pets to think about, or even a parent or loved one that needs care while you are gone. Set a plan for all of this in advance, so when your partner asks, “Who’s taking care of the kids?”, you’ll have it covered. Once I feel confident that I have a childcare plan, I can step it up and test the waters.

#5 – Warm them up for the big reveal

Timing is the key to success here. Unless your significant other is spontaneous and can drop everything at a moment’s notice, you probably want to give them ample time to prepare. It’s super important to find the right moment to bring it up. Their attitude and mood will have a major impact on the outcome. You know your loved one the best, but for me, I prefer to bring it up when my husband is super relaxed, maybe even after he’s had a few drinks. And it’s even better if we’re around friends (because they are always on my side). I may mention how much we both really need a break. The last few years have been chaotic, and we all need some relaxation, right?! I may say, “It just so happens that I booked us an anniversary trip to Key West. Your mom said she’d watch the kids for us.” Then smile lovingly (maybe some puppy dog eyes) and…wait for the reaction. There’s a great chance that our friends will chime in and say, “You have to go!”

Now you may get a “yes” in the moment, but a change of heart the next day…but don’t give up. Be patient and give them more time to think about it. My husband often gives me a lame excuse about how he can’t take time off work or how we need to fix something around the house. Either way, I just hold on to the trip until the last minute (that’s where the reminders come in handy), and I keep working on it, until he finally realizes that he does need this trip -- that we both do -- and remind him that I’ve scored a great deal and handled all the logistics, so we can just go and enjoy.


By Jen Urban


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