Would You Rather: Plan It All Or Be Surprised?

Did we ever tell you all about that time that we went to the mountains with our girlfriends and had hours and hours of amazing conversations about topics ranging from massage etiquette to men wearing ladies’ shoes?


As a blogger, I particularly enjoyed the weekend because we spent a lot of time weighing some interesting Would You Rather scenarios. I feel like that practically qualifies it as a business trip. Wonder if I can write it off on my taxes next year?

Our friend Sheri is about to have a big wedding anniversary, so she was talking with her hubby about what they should do to celebrate. Her hubby said to her, “I got this”.

A few of us kind of did a collective shudder when she told us, only because we are the planning types. We don’t necessarily want to be surprised. We like to know what we are getting ourselves into and have appropriate expectations for the event.

This is how we feel the moment anyone says that they have a surprise for us!

The rest of our group was reassuring her that it would be awesome and that surprises are fun. They liked the idea of not having to think about planning and to just sit back and relax and go with the flow. In fact, a couple of our good girlfriends said that the most romantic thing they could think of would be a surprise trip somewhere.

This is the reaction you want from someone when you are surprising them!

Half of us preferred to plan it all and half of us preferred to be surprised.

So, we decided to ask our Dose Peeps. Would you rather plan it all or be surprised? This can apply to a specific event like a special trip with your mate or just life in general. What are your thoughts?







Would You Rather: Plan It All Or Be Surprised? — 98 Comments

  1. Generally I like to plan and be in control of things…but I’m also extremely lazy. So, I’m going with being surprised – and just showing up on the right day for all the fun without any of the work.

  2. Does it still count as a surprise if I want to be told two days in advance to have the opportunity to veto it? I am not a planner so I think a surprise is perfectly okay with me. I think I can leave enough hints laying around to get what I want. I’d still like the veto thing though.

  3. This is just going to shock the pants off everyone but surprise me. I am a huge planner but I could always use a break. John surprised me this year on our anni and he did a good job.

  4. I totally like to be surprised with gifts and such, so I think I would love to be surprised with a fun trip to celebrate our anniversary. Sounds like fun to me πŸ™‚

  5. Considering the FANTASTIC job my hubby did planning my 40th birthday party and our trip to celebrate, I would 100% trust him to plan something great.

  6. I too go with the lazy factor. I would much rather my husband plan anniversaries – not because I’m lazy, but because I have to plan EVERYTHING else, I’d like him to do a little something. And I’m pretty laid back, so really, as long as he is taking an interest in me and we’re doing something nice together, sans children, I’m game.

    • You are a good wife by setting the bar low…I feel like he can definitely succeed with that attitude! πŸ™‚

  7. I’d love to be the one surprised. After planning everything else in the family from what to pack for lunch to what to make for dinner to should I do laundry tonight, I think it would be bliss to let someone else make all the decisions!

    • In my mind I feel that way, too, but in reality I know I would really still rather be in charge! πŸ˜‰

  8. I would appreciate the surprise, but I would cringe at first! I am so used to planning trips and vacations that it would be GREAT for the man in my life to plan one full of surprises for me! πŸ˜‰

  9. Sometimes surprises are good because its something different, you just relax and go with the flow (like Abby) and see what happens.

    • The fact that you are both planners helps a lot I think…chances are he would do a good job planning! πŸ™‚

  10. I’ve had fun trips where I knew I would stay the first and last nights, but not the ones in between. It made it more of an adventure it seems.
    You can deduct your trip expenses from you taxes, but I think that works only if you are actually making money from the blog.

    • Details, details. I guess getting paid in Bitcoin will probably make it hard to file taxes! πŸ˜‰

  11. I love surprises! I am totally a “go with the flow” type of person and I can make it work in almost any situation. Also, I can safely pick “surprise me: because my husband would NEVER ever plan a surprise. He hates them and would never subject another human being to one.

    • HA HA HA! Nothing better than being able to answer while knowing it would never actually happen! πŸ˜‰

    • Right??!! Business meetings with lavish spreads is my favorite kind of planning session! πŸ˜‰

  12. I hate surprises. Planning all the way. No one’s ever accused me of being flexible and spontaneous. Or fun either, come to think of it!

    • BWAH HA HA HA Liz! This just made me burst out laughing…I am not often accused of being fun either!

    • Because that is like the opposite of a surprise, am I right??!! Totally something a husband would do, too! πŸ˜‰

  13. I would love for my husband to surprise me with a trip, but if it were a surprise party for me I would hate it because I know I would absolutely without a doubt burst into tears. I hate being the center of attention and cry when I’m embarrassed. Awesome life trait, by the way.

    • I should not laugh, especially as you are sharing a part of yourself that is probably awkward for you. But I totally did.

  14. I pick be all surprised as I loathe planning and would probably be seat of the pants on that front. Plus the Caveman is an excellent trip planner and would spend more than I’d ever allow. πŸ™‚

  15. ut uh no one better be surprising me. lol I don’t surprise well. If someone at my house says “surprise mom!” it me means 1 of two things… poop or a mess

  16. I would love to be surprised. Two reasons: I’m always the one who does all the planning and arranging. It would be nice to be relieved of that job once in a while. (This is why I love Disney trips with my adult kids because they are fanatics and plan everything – I’m just along for the ride!)
    Second reason – I tend to be cheap and my dear husband is not so any trip he plans will be a bit more luxurious…no complaints about that!!

    • You would be the perfect person to surprise then Mo! I will email your hubby secretly right now! πŸ˜‰

  17. I’m not the best planner, so I’d like to be surprised. Even though I don’t like being the center of attention. Still, it would be nice to know people planned stuff for me.

  18. Surprise me!!! Actually sort of shocking since I have serious control issues but true. Chris planned a surprise trip every year for our first 10 anniversaries. Sadly we had to quit because we didn’t have anyone to keep the boys after those but soon they will be old enough to stay a few days on their own!!

    • Oh my Gosh, that is SO SWEET of him Kim!! πŸ™‚ Tell him that the next one will have a big one since you have had to skip a few years! πŸ˜‰

  19. I like to be surprised, as long as it’s a good surprise. I make the kids wait to open gifts until whatever special day we are celebrating arrives. My husband on the other hand would open all the gifts right away. Now that I think about it, the crazy thing is I’m a planner too.

    • Isn’t that interesting Chastity? I actually am a planner, but definitely hold off on opening gifts until the appropriate time, too. πŸ™‚

  20. Oh, I’m definitely a planner. It’s shameful, really. But if I don’t plan it, I don’t know what to wear, whether or not to put on makeup, or actually put some thought into my hair. You know…instead of just throwing on whatever fits that’s presentable for the day. I love surprises…but only if I’m the one planning them.

    • HA HA HA! I have a feeling in the same boat I would definitely be hitting the local Target for some forgotten items! πŸ˜‰

  21. Surprise! I ABSOLUTELY ABHOR SURPRISE PARTIES. There. Said it. My late husband agreed to allow my running pals and his workmates to organise a surprise baby shower for me a mere 3 weeks after our first child was born. What was he thinking? Picture it: you’ve had a whole 2 hours of sleep the night before and you’ve not considered a shower (the hair washing kind) for yourself. You are in your standard baby attire – baby puke decorated sweats. Contemplating an afternoon of nursing and more nursing. “Ding dong!” Doorbell? Doorbell. Window peek reveals huge balloons, excited well rested fit nicely dressed women. Majority of them complete strangers to you. Oh my god. Noooooooooooooooooooooooooooo …

    • OH MY GOD. Kelly, that is the WORST!! I seriously cannot imagine the horror you must have felt in that minute!

  22. I hate surprises. Truly. I’d rather plan it all. I’d rather be prepared than caught in an uncomfy situation if I didn’t like what the surprise was and trying to be excited or happy when I’m not. I just can’t pretend to like something when I don’t. I’m too honest. LOL πŸ™‚

  23. Oh boy. In general, I don’t like surprises because I’m so type A. Also because usually when my husband tries to surprise me I either A) find out before the big reveal or B) am super disappointed and then have to act as though I love it. Either way, it’s not good!

    • I know exactly what you mean! I have definitely had to do the whole pretending I loved something, and it is not fun at all!!

  24. LAUGHING SO HARD RIGHT NOW!!!! Oh you pick the BEST videos to portray your hilariousness!!!

    Please oh please don’t – I repeat- DON’T surprise me! Unless it’s Ed Mcmann with a check. Then I will gladly be surprised! BUT I will freak if the tv cameras are there. Cause I will surely be in my fleece pj bottoms and hair glued by grease to my head and mascara smeared down my face. THAT would not be good. But I’ll do it for the money. Any day.

    • That is EXACTLY how I feel, too! Ed can surprise me anytime…although, I think he is dead, so that really would be the ultimate surprise! πŸ˜‰

  25. I’m not a big surprise person. I would not mind if my husband planned something…in fact he usually does because planning is not my strong point right now…I have too much going on, and I can’t juggle anything else. The last big surprise he planned for me was 15 years ago and he had both of my college roommates fly out for my birthday. That was a wonderful surprise!

    • That is a fantastic surprise, so I can definitely see why you would trust him to plan something fabulous! πŸ™‚

  26. I want to plan it all, but then realize the best moments are the ones you never really expect. I have learned to let go control and just be and enjoy what life brings…so even though surprises scare me, I still rather be surprised.

  27. Ooh, when I saw the title of this come up in my email subscription earlier this week, I knew I couldn’t miss it! See, some days (my birthday, Mother’s Day..) I would give anything for just ONE surprise. But really, if it came down to it, let’s get real- Plan. It. All. There is simply nobody as efficient as I am. In this house, of course… πŸ™‚

    • I cracked up at this comment Stephanie, as I feel like this is EXACTLY how I feel about this topic. Perfectly said my friend.

  28. In theory, I love a good surprise, but I’m also a control freak. But since Sam planned a really awesome engagement (that was definitely a huge surprise), I have total faith in his abilities. And honestly, I’d rather not think about all the little details and have him do it all!

    • Sounds like Sam definitely gets an award for knowing how to plan a cool surprise, so I would totally trust him, too! πŸ™‚

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