She loves all the little surprises you shower her with. She glows when you bring her flowers and tells all her friends when you leave her notes. You’ve mastered the art of the sweet surprise but pulling off a big surprise takes planning, organization, and really knowing your woman. If you think you’re lacking in any of these skills, don’t even try. If you think you have what it takes to really surprise your girlfriend, read on.

Step 1 – Do your reconnoissance.

Ask her friends what she likes. Ask her family for suggestions. Ask them to help you out. You don’t want to be alone on this in case things go awry. Calling for allies and testing the waters is important. If you’re getting a lot of pushback at this stage, abort your plan now.

Step 2 – Clear the calendar. 

Make sure she has no plans. Make sure at least one of her friends is free that day as well to help you out. And make sure there’s nothing standing in your way. If you’re planning on taking her away for the weekend, make sure she won’t be coming back to a hectic week at work.

Step 3 – Have a plan. Have 2 plans.

“Winging it” doesn’t work well for surprises. Make necessary reservations and make backup reservations just in case. If you plan on flying her somewhere, make sure both of you have valid passports and the right visas. Have a “if everything goes perfectly” plan and have a “when everything goes wrong” plan. You’re plan to take her on a week long holiday to the Mexican Riviera could backfire at the airport with cancelled flights. Make sure you have though through ways to make it painless for both of you to overcome challenges. Being stuck at the airport is exactly the kind of surprise she hates. Here’s a list of things to think about:

Restaurant reservations. Make one. Always have a backup. Bonus points if the backup is walking distance from the first one. Extra bonus points if it’s a place she loves.

Hotel reservations. Give them your credit card to make sure they have a room for you. Know where you can go in case something goes wrong with booking.

Transportation. Whether it’s making sure you have gas in your car, double checking train times or picking seats for a flight, make sure you’ve covered everything. If you’re not the one who typically takes care of tickets in your relationship, ask a female friend for help to make sure you’ve covered all your bases.

Clothes. What are you going to wear? Make sure you’ve done your laundry or paid a visit to the dry cleaners. If you need a suit, get it pressed. Get your shoes shined. Make sure she has something to wear as well. If you’re planning to take her out to a nice dinner, ask her to put on a specific dress or if you’re having her friends help you out, make sure they know to tell her what the dress code is. If you’re bringing her on a small holiday, DO NOT pack for her. Let the surprise be where you’re taking her or plan on buying her whatever she needs once you land.

Extras. Flowers, an engagement ring, balloons, a string quartet. Whatever you’re planning, make sure you call in advance and then call the day of to make sure everything is still going as planned. (We told you this would take a lot of planning and organization).

Other people. If it’s a surprise party and you need her friends to be there, make sure you tell them explicitly. Don’t assume just because you asked them for advice that they’ll be there.

Step 4 – Don’t be afraid to back out.

The perfect surprise shouldn’t be stressful for you. It should be challenging but something you know you can look forward to and something you’re certain she will enjoy. If things get messy or you’re getting overwhelmed, leave the surprise for next time. You’ll need to be able to roll with the punches, but you need to know when to quit as well. Whatever you were planning, a proposal, a birthday party, a weekend getaway will be just as appreciated knowing in advance. Surprise her with flowers anyway.


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