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Used an iPod Mini since 2006 and got my first cellphone, a flip-phone, in the summer of 2008. Loved the iPod but didn't like carrying both devices around so ended up getting an iPhone 4 in late 2010.

Currently using a 5s, however, my favorite design was one of an iPhone that I haven't owned (yet!), the slate iPhone 5.
 
I saw it when the 3GS came out, wanted it, went in the store and played with it, Walked out with one on contract and have had everyone since including the new 5S. Not much of a story and not one has failed me even though I bought Applecare + on all of them.
 
January 9, 2007: Steve Jobs announces the iPhone. I predicted it would be a total flop. I even wrote blog posts about what a stupid idea it was, and why I thought it wouldn't succeed. Owing to its high price, I even gave it a cheeky name: the iGouge.

January 30, 2007: Windows Vista comes out. Like a Microsoft fanboy, I'm first in line, and plunk down $460 on the Windows Vista Ultimate Upgrade edition.

8 hours later, I'm at home, trying to install it on my then top-of-the-line 64-bit 2.4GHz AMD X2, 4GB RAM, 750GB hard drive custom built system. And I'm realizing what a fool I was. All my data gets trashed. Nothing works.

February 7, 2007: I buy a MacBook Pro and begin switching to OS X. I'm amazed at how great it is, after years of deriding them as being overpriced playthings for artists, but nothing I'd ever do serious IT work with. Fall in love with UNIX. Never want to use Windows again.

I still think the iPhone is a dumb idea though.

June 2007: The iPhone comes out. I'm standing in the Shadyside Apple Store in Pittsburgh with friends of mine, comparing my Treo 750 (actually, the pic on that link IS my phone... I took that pic and submitted it to Wikipedia for use) to the iPhones on display. A bunch of people are around me poking at them, too.

Me: *picks up an iPhone and tries to type on one* "UGH! No hardware keys? I can't type anything properly! Everything gets misspelled!!"

Immediately, a flock of Apple Geniuses swarm on me like a strike team.

Some Apple Genius: "Sir, you can probably type better if you try with your index finger first."

Me: *loudly* "Index finger? That's a STUPID idea! Who wants to type with their index fingers?! A touch screen keyboard is the worst idea, ever!"

Saying this was like striking a nest of wasps with a baseball bat. These half dozen or so Apple Genii totally go into damage control mode, contributing to the scene I just made. My friends pull me out of the store before things get nasty.

June 29, 2007: An iMac at work goes on the fritz (bad WiFi card) and needs to be taken into service. I lug this iMac into the Apple store (a different one) and have to wait around while the Genius tries a few things and fills out his forms. While I'm waiting, I see the display of iPhones again. I go over and play with one.

30 minutes later...

Apple Genius: We'll have that iMac fixed for you by tomorrow. is there anything else?

Me: Yeahhhhh... one 16GB iPhone, please.

And I've not looked back since.
Haha this story is awesome! :D
 
I've had every iPhone model since the original was announced in 2007. I briefly went from the iPhone to a BlackBerry because of work in 2008, but came back when the 3G was released and have purchased every model since.
 
The Intro

The path with iOS started when I bought my wife a second gen iPod touch. I liked the idea of a media player with a built-in web browser, but didn't pull the trigger until the app store went live and I saw the incredible array of apps coming out.

Once that iPod touch came home, it was in use all the time. When my wife didn't have it with her, I was playing games on it, and when neither of us used it, our one-year daughter had it.

The Disaster and Recovery

Unfortunately, that iPod touch ended up going through the laundry. We had the LCD screen replaced, and miraculously, the thing still worked (albeit a lot less predictably and with really bad battery life). But, my wife could not go without it for the time it was in the repair shop, so we bought a third gen iPod touch -- the first one with a camera and retina display. I wound up with the other iPod, and carried it with me along with a feature phone.

The Miracle

Three years ago, I talked my technophobic parents into buying an iPad 2, primarily so they could FaceTime their granddaughter. Understand that my mom had never touched a computer. Yet, FaceTime was so simple that she regularly used it, as well as several other apps.

One year after that, they bought an Apple TV, and now use that with the iPad for watching movies and old TV series.

I regard that iPad as a miraculous device, because it brought my mom out of the dark ages in a way that a PC never could. It keeps her connected to our daughter, and it keep adding functionality as she branches out into new apps.

The Family Grows and the Seed is Planted

Two years ago, we pulled the trigger on the iPad 3 (I was waiting on the retina display to go large before buying an iPad). As before, the iPad has everybody in the house clamoring for their turn.

But, unlike our other iOS devices, I bought the cellular-enabled iPad. This was our first celluar data-enabled device of any kind, and the flexibility of the contract-free, data-only plans allowed us to see if we liked it without having to commit to a contract and to only use the mobile data when we actually needed it.

Turned out that having mobile data was pretty cool (although we still only use a $30 1 GB/3 month AT&T plan). Up to this point, none of us had smartphones ... yes, up to this point.

A Hold Out Falls

Ever since the iPhone came out, I gave only fleeting thought to getting a smartphone. Yes, it had cool functions that I might use and use quite a bit. But, I could never get past the ridiculously opaque and confusing cell plan pricing. I did the math, and found the subsidies and contract terms to be a ripoff. The data allotments were a joke.

Loved iOS, hated the telcos. So long as the iPhone was joined at the hip with the telcos, I stayed out.

Then one-by-one, the barriers cracked. More MVNOs began supporting the iPhone. Apple started selling factory unlocked iPhones. T-Mobile went contract-free. AT&T began offering more realistic data allotments with their prepaid plans. By last summer, it was time to start looking again.

After weighing the options and doing the math based on my particular usage needs, I decided on T-Mobile's $30 prepaid plan (low minutes, high data, no contract). Then, it came down to deciding between buying the iPhone 5 and waiting on the 5s.

Ultimately, I decided to wait a few extra months for the newer models. Midnight on Sept 20, I ordered the 5s right when Apple's site went live, and haven't looked back.

And that's the story so far...
 
The Intro

The path with iOS started when I bought my wife a second gen iPod touch. I liked the idea of a media player with a built-in web browser, but didn't pull the trigger until the app store went live and I saw the incredible array of apps coming out.

Once that iPod touch came home, it was in use all the time. When my wife didn't have it with her, I was playing games on it, and when neither of us used it, our one-year daughter had it.

The Disaster and Recovery

Unfortunately, that iPod touch ended up going through the laundry. We had the LCD screen replaced, and miraculously, the thing still worked (albeit a lot less predictably and with really bad battery life). But, my wife could not go without it for the time it was in the repair shop, so we bought a third gen iPod touch -- the first one with a camera and retina display. I wound up with the other iPod, and carried it with me along with a feature phone.

The Miracle

Three years ago, I talked my technophobic parents into buying an iPad 2, primarily so they could FaceTime their granddaughter. Understand that my mom had never touched a computer. Yet, FaceTime was so simple that she regularly used it, as well as several other apps.

One year after that, they bought an Apple TV, and now use that with the iPad for watching movies and old TV series.

I regard that iPad as a miraculous device, because it brought my mom out of the dark ages in a way that a PC never could. It keeps her connected to our daughter, and it keep adding functionality as she branches out into new apps.

The Family Grows and the Seed is Planted

Two years ago, we pulled the trigger on the iPad 3 (I was waiting on the retina display to go large before buying an iPad). As before, the iPad has everybody in the house clamoring for their turn.

But, unlike our other iOS devices, I bought the cellular-enabled iPad. This was our first celluar data-enabled device of any kind, and the flexibility of the contract-free, data-only plans allowed us to see if we liked it without having to commit to a contract and to only use the mobile data when we actually needed it.

Turned out that having mobile data was pretty cool (although we still only use a $30 1 GB/3 month AT&T plan). Up to this point, none of us had smartphones ... yes, up to this point.

A Hold Out Falls

Ever since the iPhone came out, I gave only fleeting thought to getting a smartphone. Yes, it had cool functions that I might use and use quite a bit. But, I could never get past the ridiculously opaque and confusing cell plan pricing. I did the math, and found the subsidies and contract terms to be a ripoff. The data allotments were a joke.

Loved iOS, hated the telcos. So long as the iPhone was joined at the hip with the telcos, I stayed out.

Then one-by-one, the barriers cracked. More MVNOs began supporting the iPhone. Apple started selling factory unlocked iPhones. T-Mobile went contract-free. AT&T began offering more realistic data allotments with their prepaid plans. By last summer, it was time to start looking again.

After weighing the options and doing the math based on my particular usage needs, I decided on T-Mobile's $30 prepaid plan (low minutes, high data, no contract). Then, it came down to deciding between buying the iPhone 5 and waiting on the 5s.

Ultimately, I decided to wait a few extra months for the newer models. Midnight on Sept 20, I ordered the 5s right when Apple's site went live, and haven't looked back.

And that's the story so far...

Great story! I love to hear about how everyone got into iOS :D I was the exact same way, I HATED the cellular plans and contracts, so i just stuck with the iPod Touch (4th gen at first, then got a fifth gen)! I was looking at the iPhone 5 last year, but the contracts were just too much and WAY to complicated!!! Now this year (a few weeks ago to be exact) I actually really sat down and did the math, and found out I COULD afford the monthly cost!! So now I'm happy with my first iPhone!
 
My iOS journey started with a first gen iPod touch a few months after it came out. I was just getting into tech at the time and I really liked the idea of upgrading my slightly broken click wheel iPod with a touch screen device. It was my first foray into iOS. Though at the time there was no App Store. Jailbreaking was what kept me tied to the system.

I eventually ended up getting an iPhone 3GS once I saved up enough money to purchase one. Though at the time I was in high school and my parents weren't willing to pay for a data plan. This got me even more invested in the iOS ecosystem as I kept downloading from the App Store.

In 2010 when the first iPad was released I dismissed it as a ridiculous device that I insisted I would never use. Because of that, I never really put an effort into trying one out. It wasn't until January of 2011 that I properly used the iPad for the first time. I was at a friend's house and it was sitting on the couch. I picked it up and once I started using it I realised just how fantastic it actually was. It was in that moment I realised I wanted one. However since it was already almost a year old and since I followed MacRumours I knew it wasn't worth it to get one then. I waited for the iPad 2 to come out and bought one on release day. I used it all the time and the various iPad optimised apps enhanced my iOS experience even more.

Later that same year I purchased an iPhone 4S to replace my aging 3GS. The speed increase was a huge welcoming change. But the retina screen was honestly the best part of that entire update. It made my iPad 2 screen (which I had purchased less than a year ago) look terrible. Based on the rumours I new a retina iPad had to be coming.

Sure enough, that next March I replaced my iPad 2 with a 3rd gen iPad. That retina screen was perfect and I used both my 4S and the iPad super regularly.

However later into the year my interest in iOS was starting to wane on the iPhone (I was still enjoying it fully on my iPad). Android had started improving considerably and Windows Phone was the new kid on the block with a fresh and exciting interface. When the iPhone 5 first came out, I was not wowed much by the upgrade so I decided to dabble a bit with other options. I picked up an HTC HD2 and had a hell of a time tinkering with that (it reminded me of how it felt to jailbreak the first iPod touch and customise it to my heart's content).

Soon after though, I started to see how unpolished and disjointed Android felt (I used Android from Froyo to Gingerbread). It was decent, but it wasn't for me. I also had to sell my iPad for financial reasons so I figured rather than replace my nonexistent iOS devices I'd just try Windows Phone instead.

For a while I was super happy with Windows Phone. I purchased the Lumia 920 and despite it being pretty bulky, it was a fantastic phone. The WP OS is super fast and fluid and I actually rate it on par with iOS in that regard. I tried to wait out the app gap, but it seemed like developers were taking ages to get the major apps to the platform. The final nail in that coffin came when I dropped my Lumia into some water. It still works, but the cellular radio is kind of flaky. I needed a replacement.

At this point (summer 2013) I hadn't had iOS in a long time and I was beginning to miss the cohesiveness between the iPad/iPhone. I also missed being able to literally find any app I wanted without wondering whether or not the developer actually bothered to create a compatible version or not.

I knew the iPhone 5S was due in a couple of months, but I needed a new phone right away. I opted for a used (but mint condition) iPhone 5 and my love for iOS was renewed.

I'm still using that same iPhone 5. And while nothing is wrong with it, I know for sure I will upgrade to the 4.7" model whenever it is released. One thing I realised from my experience with Android and WP is that 4.3-4.7" screens are my ideal screen size for a smartphone. I'm waiting for the successor to the iPad Air now that I'm in a better financial situation and I'll probably also buy that this fall along with said new iPhone.

So yeah, that's my super long and rambly iOS story.

tl;dr, my journey was first gen iPod touch > iPhone 3GS > iPad 2 > iPhone 4S > iPad 3rd gen > Andorid/Windows Phone > iPhone 5 > patiently waiting for the iPhone 6/iPad Air 2

I remember how common jailbreaking was back in those days. First off it was very easy compared to today, and secondly it just added SO much. Heck originally jailbreaking added the ability to add APPS. I think my original iPhone was jailbroken a month or so after it came out.

I actually consider modern day jailbreaks much easier than they used to be. I remember having to force DFU mode manually, move a couple of files, and check various options to get the jailbreak to work. Now it's pretty much always a one click affair.
 
It was between a Palm Pre and a 3gs for me.

They were out of palm pre preorders so I ended up getting a 3gs (lucky me haha).

Since then I started developing for ios around the time of the 4 and I really have not looked back. I think the iphone 6/iPhone air is going to be a huge launch way bigger than any other and big enough to see a large shift away from andriod.
 
My first smartphone was a Motorola Droid. At the time, my wife wanted a Blackberry, because in those days everyone in her office had one. And at the time, the iPhone was still AT&T-only, so screw that. It is true that I thought I was going to prefer the slide-out keyboard to the touchscreen keyboard, but after a while you get used to it, and I ended up not using the slide-out that much. After three years with the Droid, I switched to an iPhone 5--I could have switched sooner, but I figured it wasn't really worth it until the iPhone got 4G. By that time the Android phones had all grown into little monsters, and I wanted something smaller and lighter than the Droid. Now that the iPhone is following that trend, I plan on holding on to my 5 as long as I can.
 
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