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3GS: 2009 - 2012, (I loved that phone back then 🙂)
5: 2012 - 2018
SE2016 for a couple of months
7: 2019 - 2020 but smashed it, but it was too big anyway
SE2016 again 2020 - 2022
13mini now, probably the best iPhone yet
 
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6S Plus (still have and use it as an alarm clock)
8 Plus (traded it in for the XS Max)
XS Max (gave to my mom)
12 Pro Max (gave to my dad)
13 Pro Max (still have and use it to watch media)
13 Mini (currently using, and absolutely loving it; it's probably my favorite phone of all time)
 
4S: I lucked out in getting it. I found an iPhone 4s on an older cousin's couch, it was locked and he didn't have much use for it. He told me I can have it, a few days later I got it unlocked and had my first iPhone. It was a nice HS Graduation present.

5s: First iPhone I bought for myself, got it used on Swappa late 2014. Within the first week, I dropped it in a bucket of hot water. The rice trick did the job after about 3 days in there, Iphone was working great again.

7 Plus: First iPhone I bought on preorder.
XS Max: Preordered. 7 Plus screen breaking was my mine reason for getting it.
13 Pro Max: Bought it on the crazy BestBuy deal last year.
14 Pro Max: T-Mobile basically gave me the phone for free, so I decided to upgrade.
 
iPhone 4 in black at 16gig

iPhone 6S Plus in white at 128gig

iPhone 12 Pro Max in white at 512gig

iPhone 14 Pro Max in white at 512gig
 
iPhone 5 - Black/Slate
iPhone 6S+ - Rose Gold
iPhone X - Silver
iPhone 11PM - Midnight Green
iPhone 12P - Silver
iPhone 13PM - Sierra Blue
...iPhone 14P if 13PM breaks before 15 unveiling!

I really miss Rose Gold. Midnight Green is a close second, Product Red in third, despite never owning a red iPhone.
I know it wasn't asked for, but my Apple Watch journey has been:
Series 2 - Silver
Series 3 - Silver (SS)
Ultra
 
2005: Nokia 8801
2007: Original iPhone
2008: iPhone 3G
2010: iPhone 4 Black
2012: iPhone 5 White & Silver
2014: iPhone 6 Plus Silver
2015: iPhone 6S Plus Space Gray
2016: iPhone 7 Plus Black
2017: iPhone X Space Gray
2020: iPhone 12 Pro Max Pacific Blue
2022: iPhone 14 Pro Max Deep Purple
 
iPhone SE 1st Gen 32 GB since Nov. 2017, hopefully for one or two more years.
My only regrets : buying one so late + so little storage...
 
I'm a yearly upgrader since the 3GS, while the original iPhone and 3G had nice UIs the hardware mainly the cellular modem was really crap compared to the Windows Mobile PDA phones were at the time, wasn't until the 3GS that the hardware finally caught up.

While the original iPhone was stuck on crappy edge Windows Mobile was on was on 3G with HSDPA. The UI may not have been pretty but at least email and looking up things online were quick.

3GS 32GB
4 64GB
4S 64GB
5 64GB
5S 64GB
6 128GB
6S Plus 128GB
7 Plus 256GB
X 256GB
XS 512GB
11 Pro Max 512GB
12 Pro Max 512GB
13 Pro Max 1TB
14 Pro Max 1TB
 
2G (Original)
3G
3GS
4
4S
5
5C (about 2 months, I didn’t like the plastic back)
5S
6 Plus
6S Plus
7 Plus
8 plus (1 month)
X
XS Max
11 Pro Max
12 Pro Max
13 Pro Max
14 Pro Max

Do I have a problem? 🤔
 
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2G > 3G > 4S > 6 > 7 > SE (2016) > 12 mini

I think I only tolerated the (then) larger size of the iPhone 6 because it was novelty, but by the time the iPhone 7 dropped I was just over it. Downgraded to an SE and im still stubborn about having a small phone. Thankfully the mini came out and should last to the end of the decade hopefully lol
 
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3G - 3GS - 4 - 4S - 5 - 5S - 6 - 6S - 7 - X - XS - 11pro - 12 mini - 13pro

This is my first year not upgrading since my first iPhone. I really think the 13pro has everything I want but would have upgraded if they made the pros lighter or added promotion to 14. I really liked the weight of the mini but the battery life was horrible and the screen was just a little too small. I wish I would have just hung on to the 11pro. The 5.8 inch screen was the perfect size. My favorite was definitely the 11pro. If I could get that with an aluminum frame and 120 hz screen that would be my perfect phone.
 
3G, 4, 5, 6, OG SE, 7Plus, X, XR, OG SE again, 11 Pro, 12 mini, 13 mini, 13 Pro and now my 14 Pro.
I’ve also dabbled occasionally with android devices (a Samsung Galaxy and a couple of Google Pixels) in between/ as well but always went quickly back to iPhones.
 
iPhone 8 >>> iPhone 13 mini

I really love the 8 design, home button and screen size.
Super comfortable so I was thinking about buying SE 2022 but the battery and lack of MagSafe is stopping me.
 
iPhone 5s - iOS 8.2 (Feb 2015-Sep 2016): got it after the 6 came out because of the size, loved it. Battery life was paltry, however. Currently in a drawer, on iOS 8, with a broken screen after I dropped a powerbank on it.

iPhone 6s - iOS 9.3.3 (Sep 2016-Apr 2017, Feb 2018-Aug 2019): My favourite iPhone ever. lightning fast, significantly better battery life, headphone jack, I couldn’t ask for anything more. Tried a 6 Plus, loved the battery life, got a 7+ in April 2017. Went back to it in 2018 because of the 7+ issue. Used by a family member until recently, destroyed into oblivion and uselessness by Apple after the infamous A9 activation bug on iOS 9 which forced it into iOS 13. Currently in a drawer.

iPhone 7+ - iOS 10.2 (Apr 2017 - Feb 2018): Got it due to battery life, like I said. Came with a broken camera and some odd hardware glitch that presented itself in the form of weird glitches and crashes throughout some native apps. Used it for almost a year, got tired of the glitches and went back to the 6s. Traded in to Apple for an iPhone Xʀ.

iPhone 5c - iOS 9.3.2 - iOS 10.3.3 (Mar 2018 - Aug 2021): got it as a second phone alongside the 6s, then the Xʀ. I have no idea how I put up with that thing, though. Forcibly updated by Apple from the pretty bad iOS 9 to the unusable iOS 10 after it bootlooped. Currently in a drawer.

iPhone Xʀ - iOS 12.3.1 (Aug 2019 - current): My current iPhone. I love it. Battery life and performance are flawless on iOS 12, but my favourite iPhone ever is still the 6s, which…

iPhone 6s - iOS 10.0 (Aug 2021 - present): Got this from a family member to replace the unusable 5c as a second phone. My favourite iPhone, ever, no question. Currently in use as a second phone.
 
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7E3C354E-B81E-4981-8B19-DA5930E608F1.jpeg


2007: iPhone, 8GB. July 9, 2007 from Apple Store on Stockton in SF. Still boots. Jailbroken. Has hilarious collection of apps and old emails.

2010: iPhone 4, Black 16GB. Now dead. Just discovered battery expanded and ruptured back glass.

2013: iPhone 5s, Black 64 GB. Best iPhone ever. Still boots.

2014: iPhone 6 Plus, Black 128GB. Stolen from car while traveling

2015: iPhone 6s Plus, white 128GB. Still in use but barely.

2016: iPhone 7 Plus, Black 256 GB. Still in use

2018: iPhone XS Max, Black 256 GB. Daily driver still going strong.

202x: the first iPhone with USB-C
 
4S
5S
6 -> 6 Plus 2 months later
6S Plus
7 Plus
XR
11 Pro
13 Pro

In my opinion, the 7 Plus will go down as one of the greatest iPhones released. It had an amazing camera setup, great battery life, waterproof, solid state home button, super fast A10 that has stood the test of time, 3GB of RAM, and the matte black and jet black finishes. I still miss my matte black 7 Plus.
 
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iPhone 3GS
iPhone 4S
iPhone 6S
iPhone 8 Plus
iPhone 11 Pro Max
iPhone 14 Pro

Experimented with a few Moto X models in 2014.. and before I got my 14 Pro I tried a Samsung but I just like iPhone better. Also tried the 1st gen SE but returned it and went back to my 6S.

I was absolutely blown away by the 4S's build quality and retina screen at the time. The 6S felt like an absolutely massive upgrade in terms of speed. The 8 Plus / Pro Max I was mostly impressed by the bigger screen but I'm glad to be back to a smaller phone.

As for the 14 Pro.. the 120hz screen is my favorite part.
 
64GB iPhone 6 for 3 days in 2015 due to the size I was having headaches & nausea
64GB iPhone 6 Plus in 2015
128GB iPhone 6S Plus in 2015 (Gave my 6 Plus to my Sister)
256GB iPhone 7 Plus in 2016
512GB iPhone XS Max in 2018 (Didn't like the design of the X initially, but it grew on me so I got the XS Max)
1TB iPhone 13 Pro Max in 2021 (Current phone)
 
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