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I’d agree on the 8 Plus, in the sense that it’s the only phone I’ve had that I actually miss. I only replaced it because my mother needed a new phone, and I knew if I gave her my old one she’d accept it when she wouldn’t let me get her a new one (and because if left to her own devices she’d get some knock-off Android I couldn’t help her learn to use). I sometimes see that phone though, when I go and visit her, and though I really like my 12 sometimes it just isn’t the same.

Sigh.
 
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I'll always love my iPhone 3GS the most. Just the coolest thing ever and it will always be so nostalgic. Reminds me of when tech was constantly evolving, what a great time!
 
The 2016 SE. A thing of beauty! 4-inch is super portable and not as small as you think – I watched entire movies on it and I could still read the subtitles!

Of course nowadays, while it can still run iOS 15, the main problem with it is that iOS and many apps “assume” you have a big screen. So unlike five years ago, using a 4-inch screen has become really impractical. Things like speed, camera and battery are also problematic. But well, we have the 12 mini now I guess.
 
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Top three would be the 4S (first iPhone), X (revolutionary design), and the 11 Pro Max (just one hell of a phone & gorgeous in the Midnight Green).
 
iPhone 5S because of the size. The most similar now would be iPhone 12 mini. I would get the mini if there was a Pro version of it. As there isn't, I have to settle for the bigger iPhone (but smaller than the Max)
 
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Right now I’m loving my mini and will probably get a 13 mini. I figure the form factor will return as an SE somewhere down the road. The 4 was sexy. The 5 was nice and light. I really liked the 11 Pro, too. The 6, 6s and 7 were great, size wise. Only ones I’ve skipped were 5C, 8, all the plus/max versions.. the X and XS were so heavy!
 
I’d agree on the 8 Plus, in the sense that it’s the only phone I’ve had that I actually miss. I only replaced it because my mother needed a new phone, and I knew if I gave her my old one she’d accept it when she wouldn’t let me get her a new one (and because of left to her own devices she’d get some knock-off Android I couldn’t help her learn to use). I sometimes see that phone though, when I go and visit her, and though I really like my 12 sometimes it just isn’t the same.

Sigh.
This is pretty much my exact situation.
 
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Right now I’m loving my mini and will probably get a 13 mini. I figure the form factor will return as an SE somewhere down the road. The 4 was sexy. The 5 was so thin and light. The 6, 6s and 7 were very nice! ThE X, XS and 11 Pro were heavy! The only ones I skipped were 5C, and all the plus/max versions. Sorry for the duplicate! I thought I navigated away before posting!
 
6 plus for me.
Another 6+ here too. That phone was AMAZING - huge - a joy to use. Coming from a 4s and a 5... it was revolutionary - had insane battery life - and was just about perfect in my hand.

Phones after this one felt OK, but never quite as great as the 6+ did. After almost a year with flat sides, I think the rounded sides felt better.

I find I enjoy the screen/cameras more of my 12 Pro Max but it doesn't feel as nice as the 6+ did in the hand.
 
My original iPhone and the iPhone X were my two favorites. They both looked and felt incredible.
 
5S, 4S and 12 Pro Max.

The 4S design was probably my favorite, but I loved the extra screen real estate of the 5S. The design of the 12 took me back to that 4/5 time frame, but with all of the modern tech.
 
The iPhone 5 slate was gorgeous. My first iPhone.
My first iPhone was a 32GB 3GS. My sister's old iPhone, she gave it to me as a Christmas gift (Christmas 2011). I was on Sprint at the time (and Sprint did not get the iPhone until the iPhone 5 launch) so I used it on WiFi to familiarize myself with iOS. That was in preparation for getting the iPhone 5.

My 5 stayed on iOS 6.0.1 (jailbroken) until about 2014 I think.

The whole Black/Slate thing was a major reason I never went to the 5s. I have Spaced Out Gray on several devices now, but only because that's the closest thing to black Apple offered for those devices. Thankfully, with my 11PM it's much darker now.
 
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The 11 Pro Max was the phone that felt most comfortable in my hands...I think the flat sides of the 12 look better, but the curved sides of the 11 felt better.
 
The original iPhone SE. iPhone 5 design but with such long term OS support and amazing performance.
 
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12 Pro. Nice size screen and comfortable to handle at home and on the go. Super fast and while my battery health is at 95% it still lasts at least 2 days on one charge.
 
I'll still always have a soft spot for the 5s. Such a great phone. Waaaaay too small for me now but before the plus sizes, it seemed about as perfect as things could get.
 
My iPhone X. How I got it and why. I had the smaller ones, that were used phones including the 4, then 5 and then the SE (original) When the Iphone X was being released my dear husband who loves to tease me kept saying he was buying the 10 and what would I if he did? I laughed because paying $1000 was just not in our budget or so I thought. He kept saying it for quite a few days when I finally laughed when he once again asked me, "If I get the iPhone X what will you do?" I answered, You will never see it, as I will always have it in my hands. Not realizing then that he was testing me. I am always one to never want much of anything but I do love my phone. Little did I know that he had bought it but for me. I will always cherish the memory but it stopped working so I ended up getting the iPhone 12.
 
I phone 5 and 5s were my favorites by far. I loved the design and the bigger screen and 4G felt like a huge improvement at the time. Touch ID on the 5s was revolutionary for me too
 
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6s. Sleek, rounded edges. Great size. Still have it just lying around because I hated to get rid of it.
 
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