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I am an idiot for not recording the chat transcript but I was talking to Apple via Chat to resolve this quick issue

- I want to return my iPhone 6 Plus for a 4.7 inch but the order was under my dad's name (his account etc)

The guy told me to bring my dad to exchange it "just in case"

I told him we live in different areas and the said the following:

"Oh man, that must be tough. I would miss my dad like crazy if we lived apart. Then again, it would be a lot easier if he bought me an iPhone 6"

I was absolutely shocked an Apple rep was blatantly trolling me. I closed the chat transcript instead of recording it LIKE AN IDIOT.

He/She probably thought you were a 7 year old living at home and are now apart from each other. He/She took on the emotional side of your chat.
 
I don't see the problem either. What am I missing here?

He was being friendly and lighthearted after he'd given you the information you require. That's good isn't it?
 
"The person acted like a human for a moment and I didn't document it to try and get him and trouble!"

or

"They just answered my questions like a robot reading from a script, bad customer service!"
 
I am an idiot for not recording the chat transcript but I was talking to Apple via Chat to resolve this quick issue

- I want to return my iPhone 6 Plus for a 4.7 inch but the order was under my dad's name (his account etc)

The guy told me to bring my dad to exchange it "just in case"

I told him we live in different areas and the said the following:

"Oh man, that must be tough. I would miss my dad like crazy if we lived apart. Then again, it would be a lot easier if he bought me an iPhone 6"

I was absolutely shocked an Apple rep was blatantly trolling me. I closed the chat transcript instead of recording it LIKE AN IDIOT.

Apple probably keeps copies of their chats if you truly feel that the rep was behaving in some type of demeaning manner. Perhaps you can escalate the issue.
 
Then again, it would be a lot easier if he bought me an iPhone 6 (meaning, jokingly because material items cannot replace a family bond and this person obviously feels that way, he wishes his father would buy him an iPhone.) "

Or, attempt at clever marketing: if he buys you an iPhone, and (presumably) your Dad has an iPhone, that makes FaceTime possible, and thus makes it easier to be far away.

But I see no trolling from the Apple rep here, either.

----------

I've dealt with Apple's call centers several times, and they are definitely instructed to be more personal and friendly. It's pretty much a job requirement for them. They always make small talk with you in between technical questions.

This, exactly. Every time I've been in touch with them and present a problem that needs fixing, their first step is to come back with the "oh, I completely understand how frustrating it is for x to happen" or "I can see where that would be a problem and if it were happening to me, I would want it resolved too."

It's part of their training. They're supposed to relate with you so that you're put at ease and (hopefully) convinced that they're on your side. Admittedly, once you've talked with Apple reps a few times and they all do it the same way, it kinda gets predictable and almost comes off script-like.

And yeah, if someone isn't used to it, it can come off a little weird and reactions like the OP's can happen if it isn't done just right.
 
I worked Apple Chat and I can't remember saying anything like that. But it's not a totally out of the blue thing to say as empathy is emphasized a lot.

Was this the Apple Store Chat, btw?

Apple Store Chat, when I worked there (which was a long time ago) was exclusively for helping people buy things. Unfortunately it wasn't marketed as such which meant we would get a lot of requests for tech support, customer service, plus a lot of pranks in general.

Interesting factoid: the person you are speaking to is handling 3-4 chats at once and has about 15 seconds (iirc) to respond to the last message you sent them. Also, Apple Store Chat is all about sales conversion rate. The idea drilled into your head is that the customers are at the online store because they want to buy something. They are talking to you because they need help buying something. Any purchase they make while they're chatting with you is considered a sale you helped make.

As I was leaving, they started changing the process where we could no longer set up carts for clients and the system by which we looked at which page a customer was on started not working as well. So it might be completely different now. This was through Arise (one of Apple's many contractors for its services).
 
I am an idiot for not recording the chat transcript but I was talking to Apple via Chat to resolve this quick issue

- I want to return my iPhone 6 Plus for a 4.7 inch but the order was under my dad's name (his account etc)

The guy told me to bring my dad to exchange it "just in case"

I told him we live in different areas and the said the following:

"Oh man, that must be tough. I would miss my dad like crazy if we lived apart. Then again, it would be a lot easier if he bought me an iPhone 6"

I was absolutely shocked an Apple rep was blatantly trolling me. I closed the chat transcript instead of recording it LIKE AN IDIOT.

Grow up /trolling
 
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