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Fly Sexy: Skydiving in Hawaii

February 2, 2012

When I begged for your help with the Rioja Wines contest, I promised that if I won, I would do the following with the $250 prize:

I’m going to do something fun with the money. And by fun, I don’t mean put it toward my new car. That would be responsible. I plan on being irresponsible and I’ll share that irresponsibility with you.

Well, as you know by now, I won** the contest while I was in Hawaii. But I had a dilemma. What should I do with the money?

I thought about buying this Tiffany’s necklace I’ve loved for a long time, but just can’t justify the cost. I also considered buying a piece of art work I’ve been eyeing. I even debated blowing it all on a fabulous and overpriced dinner at The Source in Washington, D.C. (the Wolfgang Puck restaurant whose reviews Chef and I have been drooling over but we can’t bring ourselves to spend that much money on one meal).

But none of these options seemed quite right.

They didn’t seem quite fun enough.

They weren’t irresponsible enough.

And then I remembered what Katie from Domestiphobia texted me the day I went to Hawaii:

“Be sure to hit up North Shore if you can and the town of Kailua if you have time. I prefer the small artsy towns to Honolulu. 🙂 Oh and go skydiving!!! That’s where we did it and it was fantastic!!”

So it was decided. I was going to spend the money going to the small artsy town of Kailua.

Syke! (Yes, I just said syke. Hello, early 90s.)

Just like the title of this blog post spoiled, I decided to go skydiving. Okay, I should probably clarify. I half-decided to go skydiving. Because I’m a scaredy-Cat. (Get it, Cat – my name is Catherine – okay. I probably shouldn’t have to explain it. Moving along.)

I’ve casually talked about skydiving for years. It’s on the list of all the other crap I’ve talked about doing, but never actually got around to doing. You know, skydive, run a marathon, get married, write a book, actually keep a New Year’s resolution. The usual.

But here I was in Hawaii, with the opportunity to actually go skydiving, and I was scared out of my mind.

For days, I entertained the thought. I called skydive shops and compared prices. (Because clearly, price is a very important factor when risking your life jumping out of a perfectly good plane). I tried to get others to go with me. One morning, I finally worked up the nerve to book my trip, and then found out that they weren’t skydiving that day because the trade winds were too bad.

I felt like a death row inmate who had just been given a pardon at the very last second. Now, I could say I tried to go skydiving while I was in Hawaii, but the winds were just too bad. I was a total bad ass … but the damn weather got in my bad ass way.

Would you have bought that?

Well, the problem was, I still had about a week left of my vacation. So that excuse wouldn’t really hold up. I called a few other mornings, and found that the winds were still too bad.

Then, I called on January 19. My 27th birthday. And the lady said yes, they were skydiving today.

I panicked and told her I’d call back later. I couldn’t hang up the phone fast enough.

When I told my dad that skydiving was an option today, he said to me, “So, are you going to go skydiving? Or are you going to wuss out?”

I told him I wasn’t sure yet. Shortly after, as I was in the shower, his words haunted me.

Was I really going to wuss out?

I had the money. I was in Hawaii. You couldn’t ask for a prettier skydiving location. It was my birthday for God’s sake. And Katie looked like she had so much fun when she went.

And then it hit me: I cannot handle being the girl who wussed out of skydiving for the rest of this family vacation. Scratch that: for the rest of my life. As I was rinsing the conditioner out of my hair (remember, I was in the shower), I imagined my future if I didn’t go skydiving.

“Dad, I’m thinking of buying a condo/dying my hair red/joining a cult/insert whatever life milestone you’d like. What do you think?” I’d ask.

“Might be a good idea. If you don’t wuss out of it like you wussed out of skydiving,” I imagined my dad replying.

I got out of the shower and immediately began to book the trip.

Some of the fear was released when the lady on the phone basically called me a heffer.

“You not fat, right?” was one of her very first questions.

“I mean, I have some junk in the trunk, if that’s what you’re asking. Child-bearing hips, that’s for sure,” was my response. I really wasn’t prepared to defend my body this morning – especially after spending the past week and a half eating and drinking whatever I wanted while I was on vacation.

“You not too fat to skydive though, right? You not over 200 pounds? You over 200 pounds, we charge you extra. You way too fat, you can’t skydive at all.”

Phew. Her definition of fat and my definition of fat are definitely different. Happy to say, I was not too “fat” to skydive.

Within two hours, the trusty bus from Skydive Hawaii picked me up at my hotel. After making sure my seat belt was securely fastened, we were off to pick up my fellow skydivers.

bus to go skydiving, Hawaii skydive

Loving the rainbow theme

Because even when you are about to jump out of a plane, you better buckle your seat belt. Safety is key.

On the bus, I met a group of college students that were in Hawaii on a school trip. They made me feel slightly old, as well as wish I went to a different college (I don’t remember any trips to Hawaii at my school!), but they were a fun bunch of kids.

Jesus, I am old. I just called college students a “bunch of kids.” I digress.

The college kids adopted me into their group and agreed to be my jumping buddies.

Skydiving in Hawaii

The college kids

Immediately upon arriving at Skydive Hawaii, you are accosted with a clipboard and a super scary contract that you must sign before moving forward. The key points of the contract were:

  • You are going to could die.
  • You can’t sue us when if you die or get seriously injured.
  • Your health insurance will laugh in your face if you try to get them to cover any skydiving injuries.
  • You are crazier than shit to be doing this. You don’t have to do this. Actually, we suggest you don’t do this.
  • Have I mentioned that you could die?
skydiving contract

Here's where you sign your life away

contract to skydive in Hawaii

No really, you could die. OK with you?

Skydiving in Hawaii, contract

Love the bold print at the end. Not scary at all.

As I’m reading through the eight pages – each page reminding me of how I could be making the biggest mistake of my life – I hear a video playing.

Oh, it’s the maker of the parachute I’ll be using. A sweet, grey haired fellow. Great, I’d love to hear all about how effective your parachutes are. I listen to the old man talk.

“I’m here to tell you that there is no perfect parachute. My parachute isn’t perfect. It could fail at any time for any reason. Skydiving is extremely dangerous.”

That’s reassuring.  

I signed the contract. My whole reason for going – not wanting to be a wuss – is the only thing that kept me moving forward with this ridiculous plan. How much of a wuss would I be if I turned around and went back to the hotel now? I’d never live it down!

For the next hour or so, the college kids and I watched several planes take off, and the skydivers safely reach the ground.

Well, that doesn’t look so hard. They all survived. Maybe this isn’t so dangerous, after all?

But what if the fact that they survived means that I have statistically higher chances of dying myself?

Yes, that’s where my mind went. I’ve never been so scared in my life.

skydiving instructor

Big Jim and me, getting ready to go

At this point, I met Big Jim, the guy who would be tandem skydiving with me at 14,000 feet. When he started to suit me up, I expected some serious instructions. I wished that I had a notepad to keep track of all the life-affirming skills he was going to teach me about skydiving. (Speaking of wishes, I also wished that I’d worn pants, because wearing shorts with this skydiving gear is simply a terrible idea. I basically looked like I wasn’t wearing any shorts at all. And like most girls, I absolutely love my thighs. And showing them off to the world in their full glory. Insert sarcasm.)

Here was my lesson:

  • When we jump out of the plane, keep your arms crossed across your chest. Arch your back and lean backwards.
  • When I tap your arms, open them.
  • When we land, lift your legs and let me touch down first.

Umm, the shortness of that lesson was just a bit disconcerting. What about if you pass out and I need to open the parachute myself? You gonna show me how that thing works – just in case? Apparently not.

I asked him what the biggest mistake I could make would be. “I’m glad you asked. There is one mistake you can make, and I’ve seen it made tons of times. It’s really important,” Big Jim said, very serious.

Where is my damn notebook when I need it? I thought. “What is it?”

“Don’t forget to fly sexy.”

Here is the little plane in which I would be risking my life.

Big Jim swore he was having an "on-day" at work. As the plane ascended, I asked him a million frantic questions, and he answered each one calmly. Loved Big Jim.

I had just found we were going to be the first tandem group to jump out of the plane. The view was beautiful. This expression on my face is not me admiring said beauty, but me being scared out of my mind.

Everyone looks pretty intense. I took a moment to pray. Then I figured God probably didn't appreciate me praying as I unnecessarily risked my life, so I just hoped for the best.

skydiving in Hawaii

I think my eyes were completely shut during the leap from the plane.

Seriously the coolest feeling of my life.

Once I felt the tap on my shoulders, I was able to open my arms.

Of course, we had to do some peace signs and the like.

Definitely flying sexy and getting the hang of it now.

This is seriously not my normal birthday view.

Just before our parachute opened. When it did, it scared the bejesus out of me.

This is such a cool shot.

view above Hawaii

Upon seeing this view, I cried. No longer out of fear, but because it was so beautiful and I was so proud of myself for conquering my fears. I've never felt emotions quite like these before in my life.

skydiving in Hawaii

After an amazing ride, we came in for the landing.

skydiving descent

I was suddenly really scared again. I mean, this is when people break bones and stuff!

Big Jim's plan was for us to land our butts. And that we did.

skydiving end Hawaii

The adrenaline, relief and pure joy I felt when we hit the ground was overwhelming. Big Jim exclaimed, "Happy Birthday, Catherine!" It was definitely a birthday I will never forget.

I also bought a video of the experience:

Goals: Spend the prize money in a fun, irresponsible way; and make my birthday in Hawaii an unforgettable one.

Mission accomplished.

Copyright 2012. Simply Solo blog by Catherine Gryp. All Rights Reserved.

58 Comments leave one →
  1. February 2, 2012 9:14 am

    Amazing!! What an amazing thing to do in such a beautiful place! Congratulations to you Catherine. And happy, happy birthday. 🙂

    • February 6, 2012 9:18 pm

      That was one of the deciding factors for me. I could totally go skydiving in the US, but when would I ever have this view again? It was absolutely perfect. Couldn’t have asked for a better day. Thanks for reading and commenting!

  2. February 2, 2012 9:15 am

    This post really made me smile! 🙂
    (although I’m not about to go and jump out of a plane! :D)

    • February 6, 2012 9:17 pm

      LOL Rachel. Glad you liked the post….and I totally think you should jump out of a plane. But don’t sue me if something goes wrong. LOL 🙂

  3. February 2, 2012 9:17 am

    Best use of contest cash ever!

    • February 6, 2012 9:15 pm

      Thanks! I think so too! I’m glad I picked this over my other options, that’s for sure!

  4. February 2, 2012 9:22 am

    Awesome pictures and video cat!! Best way to celebrate your birthday! thanks for sharing! Wheres your next skydive? lol

    • February 6, 2012 9:16 pm

      Haha, Ashley. I don’t think this bug is out of me … I do want to do it again sometime! But I’ll take a break for a little bit, just to get used to the ground beneath my feet 🙂

  5. February 2, 2012 9:30 am

    oh my gosh katherine!!! you are incredible. seriously. i wish i were as brave as you! i dont even think id consider this — especially on my bday — but you are a rockstar.

    • February 2, 2012 9:31 am

      and i totally know your name is spelled with a c…… *CATHERINE! sorry!

    • February 6, 2012 9:15 pm

      Thank you, Mallory!! And no worries on the name. At least you remembered it at all! Thanks for reading and commenting – I had an amazing time and it was even better because it was on my birthday! Appreciate the kind words.

  6. Zak permalink
    February 2, 2012 9:31 am

    Wow. Amazing. Great job and I love the write-up.

  7. Katie permalink
    February 2, 2012 9:51 am

    It’s like I told you, if you have to die, I can think of worse ways to go than with a view of the Hawaiian islands and a hot guy strapped to your back. 😉 So proud of you and glad you had an unforgettable birthday!!

    • February 6, 2012 9:13 pm

      Thanks Katie! And I appreciate the pre skydiving pep talk!! I’m not sure I would have done it if I didn’t know you had done it and had such an amazing time!

  8. Terry Kilgore permalink
    February 2, 2012 11:09 am

    “Upon seeing this view, I cried. No longer out of fear, but because it was so beautiful and I was so proud of myself for conquering my fears. I’ve never felt emotions quite like these before in my life.”

    Reading your words brought tears to my eyes. You should be so proud of yourself! You rock!

    • February 6, 2012 9:12 pm

      Aww thank you!! That was the most moving moment of the entire experience for me. I really haven’t seen anything so beautiful in my life and I’ve never felt so courageous. I’m glad someone picked up on the significance of that moment and enjoyed that part of the post. Thank you for reading and commenting!

  9. February 2, 2012 11:41 am

    Wicked telling of a great story. Was both nervous and excited for you. Congratulations for taking both the metaphoric and literal leap.


    • February 6, 2012 9:10 pm

      Thank you!! I get nervous when I see the video – it’s like I don’t know that I survived! 🙂

  10. February 2, 2012 12:16 pm

    Awesome post! Loved it!!!!

  11. February 2, 2012 12:19 pm

    Wow! Not only am I extremely jealous, I wanted to do this in Hawaii but the boyfriend couldn’t build up enough nerve, which I then used as my excuse not to do it. I wish I has the courage you had! I am also proud of you, you definitely spent your winnings irresponsibly and conquered your fear, way to go!!

    • February 6, 2012 9:09 pm

      Aww, amanalynn! You gotta go back and do it!! In fact, I had a friend I met in Hawaii that was supposed to go with me, but then he couldn’t go, I almost backed out too. So I totally feel you. But I just kept telling myself I’d only be in Hawaii once. You can definitely still go while you are back in the states – let me know if you need a partner! 🙂

  12. Nick H. permalink
    February 2, 2012 2:11 pm

    I love watching this video. I get nervous for you every time I see it. Kinda makes me wanna skydive now….SYKE!! I will save my adrenaline rush for going 60mph on a jet ski this summer at Lake Gaston. That’s about all I can handle. Congrats on being awesome!

    • February 6, 2012 9:07 pm

      Ha, talking with you on the phone before I went almost made me back out! Lesson learned: don’t call someone who loves you and is afraid of heights an hour before jumping out of an airplane 🙂

  13. February 2, 2012 2:47 pm

    Love the look of terror and full body lockup when Big Jim pushes you out of the plane. Great job Catherine!

    • February 6, 2012 9:06 pm

      Haha, yeah I’ve never been so scared. You should see the rest of the pictures! 🙂 Thanks for reading!

  14. Aunt Patty permalink
    February 2, 2012 3:06 pm

    what a great gift to yourself!

  15. Danielle's Dish permalink
    February 2, 2012 4:24 pm

    Love this post!! So awesome! I could never do it. 🙂

    • February 6, 2012 9:05 pm

      Thanks, Danielle! You totally could. Especially once you say you are gonna do it, it’s kind of hard to back out!

  16. Victoria permalink
    February 2, 2012 5:36 pm

    Well done Catherine! Awesome clip! Watching it brought back the most amazing memories for me of when I too was voluntarily strapped to a strange guy I’d never met and let him throw me out of a plane! Best 4 minutes of my life!

    • February 6, 2012 9:04 pm

      Thanks, Victoria! Glad you enjoyed the walk down memory lane 🙂 Congrats girl.

  17. Michael permalink
    February 2, 2012 10:07 pm

    What fun! I like the spur-of-the-moment (delayed) approach. The opportunity of a lifetime and you just nailed it, even after the rethink. Cool. Great contract shots!

    • February 6, 2012 8:20 pm

      Thanks Michael! I’m just so fortunate I had the opportunity! And you know I don’t make any impulsive decisions without thinking about them a ton and calling them impulsive. That’s how I roll. 🙂

  18. February 2, 2012 10:41 pm


    I couldn’t have done it. I’d age ten years if I jumped off an airplane.

    I’m proud of you! And great story-telling and pics too!!!

    =)))) xxxxx

    • February 6, 2012 8:19 pm

      Thanks, Larissa!!! I think I probably aged about 6 months….and that was after the shoot opened, Big Jim told me he was going to loosen my harness so I would be more comfortable. He said it would feel like I was falling for a second. I tried to convince him (as we were floating) that he didn’t need to do so. I was soooo scared. He convinced me it would be OK. When he loosened the harness, I swear I almost lost my shit. I definitely aged 6 months in that moment. It literally felt like I was falling with nothing holding me up. But he was right, it’s OK. And I was significantly much more comfortable!

      Anyway, glad you enjoyed the story and could live vicariously through me. 🙂 Appreciate your reading!

  19. February 2, 2012 10:45 pm

    Great photos! But I have to say it:

    You are CRAZY.

    Or loco, as the Hawaiians say. (And 200 lbs. is nothing to them…if you’re a 200-lb. Hawaiian, you’re considered skinny). I’m sorry, but “You may die” and “You may be killed” are deterrent enough for me to remain a grounded wuss.

    • February 6, 2012 8:14 pm

      Haha, Mark. I also wondered about that Hawawiian woman calling me fat. She sounded pretty chunky herself! 🙂
      Trust me, if I’d read that contract in my hotel room, I’m not sure I would have gone. It was only pride that kept me going! But now that I’ve officially survived, I totally think you should do it. It was incredible.

  20. Debbie settles permalink
    February 2, 2012 11:02 pm

    The video was worth it !!! Wow Dallas watched it with me and loved every second now he wants to go skydiving lol

    • February 6, 2012 8:11 pm

      Ha, you will NOT let my nephew go skydiving. (Do as I say, not as I do…) haha 🙂

  21. Oh, my roaring 20's... permalink
    February 4, 2012 1:02 am

    I totally have that bow necklace. I haven’t taken it off in the two years I’ve owned it. BUT, I think skydiving was definitely the better choice! Congrats on conquering your fears! The photos are incredible.

    • February 6, 2012 8:11 pm

      Hahaha, you actually just made me wish I’d gotten the necklace. You’ve worn it every day for two years?? DAMN I WANT THAT NECKLACE!!! LOL!! Skydiving was pretty amazing. Thanks for reading and commenting. Enjoy your fabulous necklace 🙂

  22. February 6, 2012 1:31 pm

    Congrats…but nope nope nope nope nope nope. Never. Not gonna do it.

    • February 6, 2012 8:05 pm

      Thanks Matt! Really enjoyed it. I wanna convince you somehow… there’s nothing like it!

  23. February 6, 2012 7:31 pm

    O.M.G. Never would I ever…. Good for you!

    • February 6, 2012 8:04 pm

      Thanks!! I think you totally should. Scary as hell… but seriously worth it!

  24. February 10, 2012 12:28 am

    That was frickin’ awesome Catherine!! Congrats on conquering your fears and doing something so bold you can be proud of the rest of your life 🙂

  25. macie cottier permalink
    February 19, 2012 4:00 pm

    Catherine! Oh My Gosh I loved reading your blog! I’m glad we could adopt you into our family and that you had a good birthday. Thanks so much for sharing your blog and pictures with the world!!!!

    • March 4, 2012 9:59 pm

      Thanks so much Macie! It was great to meet you guys and I really appreciate your taking me in 🙂

  26. February 21, 2012 6:30 pm

    Congrats on doing something so bold and scary! It’s doing things like this that make life worth living– now you know you can conquer anything 🙂
    I have skydiving on my “life list” for the sole reason that it terrifies me even to think about… which is exactly why I should! You’ve given me inspiration– maybe someday soon!

    • March 4, 2012 9:56 pm

      You totally should! It was a blast. But really really really scary. I’m not going to lie. I almost lost my shit. 🙂 I say it’s a good item to have on your life list!

  27. February 24, 2012 11:00 am

    After reading this I think I can manage the hot air balloon ride tomorrow 🙂


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