What’s Lollipop Tuesday?

Lollipop Tuesday is a special series on The Jackie Blog, where on occasion I will try something new that I will undoubtedly suck at and share my degradation with you all in a Tuesday post.  Some may be mundane, some may be ridiculous, and when I run out of ideas, some may even be illegal.

Why Tuesday?  Because Tuesday is the most overlooked day of the week.    Mondays symbolize a new beginning – the start of a new diet attempt, the forerunner of the work week.  Wednesdays are hump day – dedicated to a celebration of making it halfway to the weekend.  Thursdays are thirsty and spent in anticipation of Friday, which is the happiest of workdays and the partier of the bunch.  Saturdays and Sundays are no contest.  And poor little Tuesday is left alone in the mix like a redheaded stepchild.  It never did anything to anyone.

So Tuesdays shall henceforth be known as Lollipop Tuesdays.  They will be a celebration of new attempts in unfamiliar territories. Feel free to chime in with ideas, which you can leave in the comments section of this page.  Who knows – I might even use yours. And if you’d like to try to suck less as well, I invite you to try a Lollipop Tuesday of your own (clicky click) and then share it with me. I’d love to hear all about it.

Here’s what I’ve tried so far:

Please note that in 2011 when I posted daily, I did one Lollipop Tuesday each week.  I now post at my leisure and when I have a Lollipop Tuesday to share, it comes in a surprise Tuesday post.
Share an idea in the comments and consider giving it a try yourself. I know it’s scary. But if an awkward hermit like me can survive a pole-dancing class, Bikram yoga, and a civil war reenactment, you’re going to be just fine. 

103 Responses to “What’s Lollipop Tuesday?”

  1. Zenalicious Mommy January 25, 2011 at 9:43 am #

    Sweet!!! Great idea 🙂


  2. jaredblakedicroce February 2, 2011 at 9:32 am #

    Science experiments (this might keep you for a bit with the proper research and an open mind…), volunteering, going to an improv/acting night (where you willingly go up on a stage with no knowledge of what you’re about to say before you’re handed a script in front of a crowd and prompted to, “Go”), Stand up comedy <- that'll test some limits… I've got a bunch more, but i won't talk your ear off. If you are indeed in NYC i can actually suggest places to do these things 🙂 Good luck!


    • Jackie February 2, 2011 at 11:01 pm #

      Jared – thanks so much for the ideas. I’m all for you talking my ear off if it means you’re sharing Lollipop Tuesday possibilities 🙂 Everything on there is certainly an option, except the improv. I’m actually an actor by night and was once the captain of an improv team so that unfortunately does not meet my new experience requirement.

      Stand-up comedy, however, is something I’ve been trying to get the guts to do for quite some time. Thank you so much for the suggestions!


  3. Lori February 8, 2011 at 10:17 am #

    I really think you should try the Diva Cup! But, if that’s not something you want to share on the interwebs (and I don’t blame you), have you ever been to a spinning/cycling class? They’re a great workout and you don’t have to be coordinated (not that you aren’t, but I’m sure not).

    Also, if you end up getting too many people to write names on slips of paper and draw from a hat, other sites have used random.org to choose winners (see: http://dooce.com/2010/11/16/dooce-xbox-joyride-giveaway-2010).


  4. Ro February 8, 2011 at 10:45 am #

    First of all, YESSSS to the tshirt win (that was totally the one I liked, since I’m really excited about the possibility of your website across my boobs). I’m not going to lie, I’ve been trying to think of some Lollipop Tuesday ideas for you since I learned what it was, and I’ve been totally a geek for your blog since your rant about armpits. …wow. So, here are a couple of ideas- for now. Hopefully I’ll have more later:
    -Lately I’ve really wanted to chop off my hair. I’m sick of it. But since I’ve sworn to let it grow to donate, I’d like to live vicariously through you. New cut, color, whatever.
    -Okay, so have you seen The Guild? My boyfriend and I discovered it on NetFlix. Cracks me up, and for whatever reason the lead reminds me of you. And it made me think, you should totally try the blog out, video style.
    -I just tried sushi for the first time. There are lots of new, gross food out there. Eat something, feel sick. It’ll be fun for us.
    -Or, even better, cook a wonderfully complicated dinner. Make other people sick, instead. That’ll be fun for the rest of us, too.
    -Try a new crafts or hobby. Knitting, scrapbooking, constructing bird houses, or hand stitch the days of the week into your underwear.
    -Ooooh. Combining those last two, totally try making a cake. When it fails miserably, post it to cakewrecks.blogspot.com. Then evevn more people can laugh at you. 🙂
    -Start a memior. It’s the cool new thing to do.
    …so… that’s all I have for now. …the end.


    • Ro February 10, 2011 at 10:52 am #

      Oooooh! Dr. Horrible’s Sing Along Blog is my new favorite thing. Do a singing blog!!! Or try to take over the world. That could be fun, too. Or spend a day at a homeless shelter. Or dig a spork into your leg. Joss Whedon is so innovative. bhahahahaha.


  5. Zenalicious Mommy February 8, 2011 at 4:58 pm #

    If it doesn’t have to be a single attempt then perhaps you could start a worm compost 😉 So trendy and environmentally friendly.

    Or here’s a few other suggestions:
    – Eyebrow threading (quiet an experience)
    – Accupuncture (would your health insurance cover that?)
    – Professional bra fitting
    – Scavenger hunt


  6. Caitlin February 8, 2011 at 6:53 pm #

    Alright – here we go. I’m gonna just sit here in my bed and give you every fabulous or lame idea I can think of. I want a freaking t-shirt!!


    – Reconnecting with Kindergarten craft day – make something paper mache or out of popsicle sticks

    – Learn to knit

    – Read a book or watch a movie you swore you’d never read/watch

    – Volunteer someplace you’ve never volunteered before

    – Go an entire day without one sarcastic comment (I’m curious to see if you’ll ex/implode)

    – Eat a gosh-be-damned PLUM!!!

    – Sing. In. Public. (not as a character, but as yourself)

    – Learn the same phrase in 10 different languages

    – Attend a service of a different religion

    – Dress as a mime and do some sort of mild mime stunt (like “picking flowers” outside your apartment for half an hour)

    – Get your shoes shined

    – Watch a foreign film you’ve never heard of

    – Find out how many licks it takes you to get to the center of a tootsie pop

    – Attend an orchestra concert or ballet

    – Go get a professional massage

    – Spin Class!

    – Use a neti pot (do you do that already)

    – Take a cooking class

    – Take a lesson in something from someone on Youtube

    Ok – I think that’s all I have for right now.

    Love you.


    • pezcita August 15, 2011 at 9:10 pm #

      Didn’t Stephen King have this running joke about (against) deifying plums? It was the funniest part of his biography!


  7. Ker-Bear February 8, 2011 at 10:16 pm #

    OK… so here are a few that I’ve come up with:

    Rock Climb.

    Be an EMT for a day… take CPR/1st Aid ,run calls, drive an ambulance, etc. -&/OR- Become a fireman for a spell: put on fire gear, learn the tools, do some practical/training exercises.

    Work a summer camp for children (I know a great weekend bereavement camp).

    Run a 5K (I plan on doing one this summer, you can join me).

    Go Scuba Diving… Sky Diving… Skinny Dipping! 😉

    Bungy jump.

    Go to a diner & buy a little old man who is eating alone his dinner… don’t tell him, just take the check & leave. Also works with someone that looks down on their luck!

    That’s all I can give ya for now. I will work on others in the meantime.


  8. Tara Schiller February 8, 2011 at 11:20 pm #

    Love this idea! Way to get out of a rut… if that even applies. Here is my idea:
    FAN MAIL! Write a letter of adoration to a favorite author, actor, or singer. You never know. They could be so moved by your letter that they invite you over for dinner and decide to be your best friend. It could happen…


  9. sheila February 9, 2011 at 8:51 pm #


    you should…

    -make your own paper camera and see if it works (it’s a real thing! google it!)

    -eat nothing but asparagus all day…see how this effects you…

    -write the opening chapter/scene of your debut novel/play and post it

    -dine and dash (do you dare?)

    -superglue a quarter to the ground and sit around for a few hours to see how many people try to pick it up (classic)

    -write a last will and testimony (dun dun DUUNNN)

    -eat 25 lbs of chocolate so you can get its benefit as a legal psychoactive drug

    -don’t let yourself watch TV or play video games for one week (see what else you accomplish)

    -try a food that scares you (bull testicle, anyone?)

    -do a self breast exam (its for your own good!)

    -try your hand at conceptual art

    -have a big (verbal) fight in public

    -learn to read tarot cards

    -cut someone in line to see how they’ll react

    -get a radical new haircut

    -ignore your cell phone for one day

    that’s all i got for now…


    • Tall Pajama Man March 18, 2011 at 9:50 pm #

      sheila, you have a great list of things to try. I might have to try some of these…


      • Jackie March 19, 2011 at 4:48 pm #

        oooh do! and blog about it! haha


  10. Brad February 10, 2011 at 12:17 pm #

    Draw cartoons of everyone you know, and display them on the website. I’m talking captions and ascessories and the works.


  11. Jeff_the_Jew February 10, 2011 at 4:40 pm #

    You should try and keep Kosher all day. It’s harder than you think.


  12. Devin February 24, 2011 at 8:29 am #

    Write a song, then perform it.

    or you could eat a goldfish.


    • Jackie February 24, 2011 at 9:08 pm #

      the mere idea of eating a goldfish is simultaneously disgusting and morally opposable. but I love it nonetheless.


      • phonymahoney March 19, 2011 at 12:52 am #

        My sister swallowed a live one to get into a party. In the projects. Which part is worse?


        • Jackie March 19, 2011 at 4:45 pm #

          LOL thanks for sharing.


  13. Podunk March 20, 2011 at 1:51 pm #

    Maybe you could pop in to the library and check out a book in a genre you never read. And then read at least the first 20 pages.


    • Jackie March 20, 2011 at 2:27 pm #

      Not a bad idea! Thanks for sharing 🙂


  14. KristenSays March 21, 2011 at 3:46 pm #

    OK I’m new to your blog and absolutely love your writing style. And since tomorrow is Lollipop Tuesday and you’re going to try something new, why not come over and help me cut my cat Lulu’s claws? She twists & screams bloody murder, and I can get about one a day. Which means that by the time I finish them all, I just have to start over. Which really cuts into my free time. So I figure it’s a win-win. You: something new CHECK. Me: Lulu’s claws cut in one sitting CHECK.

    But if you can’t make it, I really like someone’s suggestion of sewing the days of the week into your underwear. And the mime is pretty good too. And singing in public, like at a restaurant during dinner or something. Just stand up and belt out one of those classic ’90s songs! 🙂

    Happy writing!


    • Jackie March 22, 2011 at 12:06 am #

      haha thanks for the suggestions! I actually thought about doing the claws thing tonight for my own hellian, but I’m sure I’d severely injure her. She can’t stay still; it’s impossible. I will, however, consider the days of the week underwear. 😉


      • Lori April 20, 2011 at 9:04 am #

        The solution to a cat that won’t stay still for nail trimmings is to burrito them. Wrap them in a blanket and only let the paw you need out. I’m serious.


        • Jackie April 20, 2011 at 7:17 pm #

          I keep imagining this with different paws coming out of the burrito. hilarious.


  15. Adora March 27, 2011 at 6:05 am #

    I absolutely LOVE this concept! A friend and I are going to try to implement it (we can get lazy and end up in front of the tv with a movie). One thing I want to try is laser tag.


    • Jackie March 31, 2011 at 10:24 pm #

      Definitely do! First of all – you should do it because you’ve never done it before – but most of all, it’s a FREAKING AWESOME TIME.

      lol sorry.. I feel very strongly about the awesomeness of laser tag. It’s like paying 10 bucks to be 10 years old. Glorious.


  16. Sarah March 30, 2011 at 11:26 am #

    – Put wedding music on and throw rice at random couples from your window (I actually did that with my roomie)
    – Ball room dancing (fancy dress and shoes recommended)
    – Go to a restaurant, the movies or a play alone
    – Make a round in your building/block and collect funds for the WWF
    – Go to a beauty counter and ask one of the sales people to make you up, then go home, change into dressy clothes + heels and clean your place
    – At a bookstore/movie store go through the shelves and randomly put your finger on a book/movie and read/watch it.
    – Take up a Tai Chi class
    – Go to a wine tasting course


    • Jackie March 31, 2011 at 10:43 pm #

      Thank you so much – I love these!


  17. A. Ryan April 4, 2011 at 7:42 pm #

    Dog walking or pet sitting! Tuesdays is usually my ten dog Tuesday. I care for 4 Newfies, 2 Goldens, 3 Cavaliers, and 1 Pekingnese who really thinks he is a Newfoundland! Get them out for their business details 3-6 times a day depending on the client’s needs etc…feeding and lots of puppy love, attention and massages for all canines! It is a fun time and obviously you really have to love dogs!


    • Jackie April 6, 2011 at 4:36 pm #

      Ten Dog Tuesdays – I like that 🙂 I can’t imagine caring for all of them at once!


  18. rachelleverton April 15, 2011 at 12:10 pm #

    You should walk around town with your camera, and ask random people to take pictures with you. I’ve done this before with my friends and it’s highly entertaining.


    • Jackie April 17, 2011 at 12:39 am #

      oh that’s definitely a good one – thanks so much for sharing!


  19. Alyson April 17, 2011 at 3:41 am #

    Was looking up sock bunnies and came across your site (which, on Google, is right after the site you reference) – cracked me up! You sound like me – I wouldn’t have the patience to wait for the sock to dry either. (And just FYI – the Magic Eraser was the most frequently suggested favorite cleaning product in a recent Real Simple magazine poll!)

    How about hosting a Tupperware or Mary Kay party? Or a Bunco party?


    • Jackie April 20, 2011 at 7:35 pm #

      I don’t know if I could get away with that being a “new” experience because I used to sell that stuff – but maybe I could come up with some kind of twist 🙂 Thanks so much for stopping by and sharing! Did you ever get around to trying a sock bunny?


  20. jensfoodadventures May 24, 2011 at 12:35 pm #

    This is great! I’ve made a vow to take on one adventure a week.

    Try disc golf – most courses are free, discs arecheapand way easier than traditional golf. If you’re in cleveland I’ll show you how!


    • Jackie May 25, 2011 at 4:06 am #

      YES! just one new thing every week! It’s such a great thing to do for yourself. Let me know how it goes 🙂

      I was once a pretty avid disc-golfer, actually, so I can’t do that one. Buuut I’ve never been regular golfing. 😉


  21. Mitzi Magpie May 25, 2011 at 12:08 am #

    Congrats on being Freshly Pressed! That’s how I found you.

    Lollipop Tuesday is such an awesome idea!! My suggestion: learn/try to play the bagpipes, or violin. I don’t know how you would go about borrowing a set of bagpipes unless you know someone who plays; but you should be able to rent a violin for a day from a music store. 😀 I’m sure that all kinds of hilarity would ensue because it would probably really scare your cats. 😉


    • Jackie May 25, 2011 at 3:24 am #

      Thanks! So glad you dropped in 🙂 If I can get my hands on a bagpipe or accordion… or lessons for either, that would just be the bee’s knees. Love the idea – thanks!


  22. eva626 May 25, 2011 at 12:25 am #

    host a HUGE brunch party for the neighbors!


    • Jackie May 25, 2011 at 3:22 am #

      nice! I love that idea 🙂 I have a lot of neighbors so that would be quiiiite an undertaking. (I live in an apartment). Thanks for sharing!


  23. kitchenmudge May 26, 2011 at 12:51 am #

    No excuse for running out of ideas. If all you need is something at which you will surely suck, think of how many musical instruments there are. No one will be any good on any of them without practice (barring the occasional genius).


    • Jackie May 27, 2011 at 6:36 pm #

      yes definitely – agreed! plus I’ve got this huge long list from all you awesome folks. No excuses for the whole year because there is enough right here. Thanks for moseying on by 🙂


  24. thesunnygirl May 26, 2011 at 6:58 pm #

    What a great concept! I love this. I have a similar list, which I call my Sunny Set if you want some extra inspiration:


    Best of luck with your Tuesdays and every other day of the week. I hope you find happiness in each day!

    Keep shining,
    The Sunny Girl, Lauren Cook


    • Jackie May 27, 2011 at 6:31 pm #

      oh how lovely! Thank you for sharing!


  25. Marylou June 6, 2011 at 1:40 pm #

    I think you may have inspired me. 🙂 It may not be Tuesday, but having a weekly Lollipop day is a great idea.


    • Jackie June 7, 2011 at 7:56 pm #

      As a bit of a disclaimer, Tuesdays are just the day I have delegated to blogging about my experience. It holds me accountable to do something new once a week, even if not on a Tuesday. But yes, absolutely – I’m so glad it’s got you thinking. Give something ridiculous a try and let me know how it works out. 🙂 Hope the married life is just lovely.


  26. sinavratil July 6, 2011 at 12:33 pm #

    Your blog is entertaining and realistic. I love your Lollipop tuesday idea.
    Suggestions: 1. Try walking backwards everywhere you go for one hour. 2. learn a card game. 3. volunteer at a shelter (homeless or animal). 4. Go christmas shopping in July.

    Thanks for writing! Keep it up!


    • Jackie July 9, 2011 at 9:43 pm #

      Thanks so much, Sin. Ooooh I like the idea of volunteering at a shelter especially. Thank you for the great suggestions 🙂


  27. Laura July 7, 2011 at 5:12 pm #

    I found you via freshly pressed and added you to my reader. Love the post-a-day idea.

    I’m actually doing something like a lollipop Tuesday year, something new every day, but I do get behind in posting.

    Feel free to check it out for any Lollipop ideas, and I may teal one or two as well!


    • Jackie July 9, 2011 at 9:30 pm #

      Thanks so much for checking me out and for linking your blog. I love it!


  28. pickle August 15, 2011 at 2:02 pm #

    Love this idea! I randomly think of things I want to do and then do it…like learning how to skateboard…piercing my ears…dying my hair black with blonde stripes in the front (fondly referred to as my skunk stripes…)

    Check out the Bucket List portion of my blog…if you use any let me know so I can read how it goes!!


    • Jackie August 17, 2011 at 9:02 pm #

      LOL “Find my abs” is hilarious. And I ADORE the “get locked in a store overnight” that sounds fantastically scandalous.


  29. Dark Star Rising August 15, 2011 at 3:44 pm #

    You should hand out balloons (or lollipops) in a bunny suit! Why not?



    • Jackie August 17, 2011 at 8:42 pm #

      LOL That could be just slightly disturbing to passersby… but perhaps that’s all the more reason to do it.


  30. pezcita August 15, 2011 at 9:14 pm #

    If you’ve never done it before, you might want to try baking a pie from scratch. It’s loads of fun, but it’s also nearly impossible to get them to turn out perfectly. Visually perfect that is, making a tasty but ugly pie isn’t hard at all!


    • Jackie August 17, 2011 at 7:44 pm #

      I never have! I like that one. Sounds like it could be a glorious mess 🙂


  31. igardendaily August 16, 2011 at 1:17 am #

    Cool blog, love your premise. For a new Lollipop Tuesday idea how about planting an herb garden or since it will be Fall soon, planting spring bulbs. Getting your hands digging in the dirt always seems to be a bit fun… Look forward to reading more….


    • Jackie August 16, 2011 at 9:54 pm #

      Thanks so much! I’d have to fashion some sort of window garden, as I live in the city – but that could be part of the fun! thanks for the idea and for dropping in 🙂


  32. ikokitu August 16, 2011 at 10:02 am #

    Take a homeless guy out on a fancy dinner


    • Jackie August 16, 2011 at 6:59 pm #

      oooh very cool. I wonder how I’d manage to do so without the assumption of flirting 😉


  33. Neeka August 18, 2011 at 10:11 pm #

    Hmm… Okay, how about THIS:

    Set up a stand and sell gum. I don’t mean packs. I mean, sell INDIVIDUAL sticks/squares of gum.
    Or(I saw a guy in Times Square do this) go to a crowded street and start offering “free hugs.” 😀 Crazy enough?


    • Jackie August 20, 2011 at 10:23 am #

      LOL thanks for the suggestions!


  34. themcrmysoldierpotpourri April 21, 2012 at 10:44 pm #

    I love this blog! Very funny!


  35. savankiran101 August 31, 2012 at 12:42 am #

    take a board game and a few of your best buddies to the most ridiculously busy area, sit down there and go about playing the game as if you don’t give a damn to the world


    • Jackie September 6, 2012 at 12:34 am #

      love it! now I just need some friends…


  36. donofalltrades March 4, 2013 at 2:49 pm #

    See if your local police department allows ride alongs. That can be fun and interesting. Riding in the front of the care without handcuffs, of course!


    • Jackie March 5, 2013 at 1:27 pm #

      I have an EMT friend who offered to let me take an ambulance ride, but I pass out at the sight of blood. Perhaps this is a better option 😉 Thanks!


  37. Bella March 20, 2013 at 10:17 pm #

    Babysit a bratty child (neighbour’s, friend’s or relative’s kid) for the day. Try to make him/her slightly less bratty by the end of the day.


    • Jackie March 20, 2013 at 11:45 pm #

      Super Nanny: Jackie Edition. Nice!


  38. bikerchick57 March 30, 2013 at 3:06 pm #

    I have a few ideas: 1) Get a tattoo. 2) Learn how to drive a motorcycle. 3) Sing an Adele song on karaoke night. 4) Swim 10 laps at the pool (that’s the number I started with).


    • Jackie April 3, 2013 at 11:47 am #

      I’m a terrible swimmer. In that I don’t even know if I can be considered as truly knowing how to swim. I love that idea – I should certainly consider at least a class. Thanks!


  39. jfoerhirsch April 1, 2013 at 5:55 pm #

    Try bathing a cat sometime. It’s a fine line between brave and stupid…


  40. Ice_Badger June 7, 2013 at 4:50 am #

    hmmmm…maybe this will make tuesday not the worst day of the week…


    • Jackie June 10, 2013 at 12:11 am #

      Is Tuesday the worst day of the week? Actually, it kind of is. You’re still in the first half but not fresh, and you can’t use the tired Monday excuse… Here’s to more Lollipop Tuesdays 😉


  41. Shannon June 7, 2013 at 1:44 pm #

    Enjoyed your freshly pressed post on dance! Here’s an idea, become pen pals with a soldier or marine overseas and send them care packages. Beneficial to them, which will make their day, and you make a new friend, all while being helpful and showing love. (:


    • Jackie June 9, 2013 at 11:50 pm #

      This is a great idea – thank you!


  42. JenerationLife July 19, 2013 at 2:45 am #

    Genius and creative idea!


  43. technophile9 July 30, 2013 at 4:03 pm #

    Lollipop Tuesdays? What about Cotton-Candy Thursdays?


    • Jackie August 7, 2013 at 6:44 pm #

      Throw the elevator pitch at me and let’s try it. 😉


  44. scarlettsands August 6, 2013 at 12:48 pm #

    awesome idea and fricking awesome blog 🙂


  45. lolaclementine December 12, 2013 at 6:27 am #

    you’re so cute and i feel like we could be friends.

    that is all!


    • Jackie January 2, 2014 at 11:29 pm #

      We could be friends because my cat’s name is Lola. Or maybe not because I only have room for one Lola. I’m not sure.


      • lolaclementine January 7, 2014 at 6:30 pm #

        I vote for yes. Two Lola’s is never too much.


  46. dharrisxv January 16, 2014 at 7:46 am #

    WOW! Love the idea of a different challenge and pushing your boundaries – so therefore I chanellenge you to go hand-gliding! Such a great name too…Poor Tuesday!


    • Jackie January 25, 2014 at 11:16 pm #

      that would be absolutely terrifying. I should definitely do it. I wonder how much a thing like that would cost me… there is research to be done.


  47. Little Miss Menopause January 24, 2014 at 2:06 am #

    You’re adorable! Plus I have a dog named Lola. But seriously, Lollypop Tuesday…LOVE, LOVE, LOVE! Can I put it up as a “sticky” on my blog. Okay, okay…bad. But everyone gets one miss after 11 pm at night. Don’t they? Can’t wait to follow you.


    • Jackie January 25, 2014 at 11:09 pm #

      haha thanks for the love and thanks so much for following – I really appreciate you dropping in.


  48. FitsofWit January 24, 2014 at 10:52 pm #

    Hi! I’ve stumbled across your blog and LOVE this idea! I love bucket lists and pushing boundaries to prove we can do what we once thought was impossible. Kudos, and I’ll follow you for future adventures!


    • Jackie January 25, 2014 at 11:06 pm #

      Well, thanks! I’ve certainly grown a lot in the process even though every time I do one I get a lot of anxiety. 🙂 Thanks for tuning in! I like your blog name, and I also have to say that you should absolutely go get a professional massage again. Only get it at a high-end place, though. Pay at least 60 bucks for an hour. And get a chick. Never a dude.




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