I was recently out of town for a work trip and saddled up to the hotel bar, enjoying my allotment of expenseable per diem alcohol. Drinking alone at a hotel bar can sometimes be awkward, but you quickly learn what all bartenders already know: it's fun to listen in on other people and silently judge them.
I was watching this guy hopelessly flirt with a girl sitting at the bar, too. His pickup line? "Is that an iPhone? Do you like it? What apps do you have?"
It took every fiber of my being to not puke all over the place. Instead, I think just did a whole-body cringe.
First, it's time to stop acting like having an iPhone is anything special at this point. In the first few years of their existence, it was slightly unique. But now any mouthbreathing idiot can walk into a local Walmart and buy one for $49. iPhones are the new Razr phones. Soon they'll be giving away older models for free when you upgrade your McDonald's meal to the larger size.
Don't get me wrong, the iPhone is amazing. It's just not amazing in that, "oh look, we have something in common to talk about at the bar" kinda way. What kind of a question is, "Do you like it?" Of course she likes it! Up until this point, it was a great tool for making herself look busy so idiots like you wouldn't come up and talk to her at the bar.
Lastly, the apps question. C'mon, dude! It's like digging deeper into a hole you've already fallen into face-first. What better place can this conversation possibly go? Is your follow-up going to be, "I've got a great QR code reader I can recommend!" or "Oh, Angry Birds? Me too! Don't you just hate those sneaky green pigs?"
If she had a prototype iPad 7 with 3-D glasses and an attached USB espresso machine, maybe that's something to start a conversation about. Something like, "HOLY SHIT, WHAT IS THAT THING?" is a great starting point. Otherwise, you gotta show up with something more to offer. Or better yet, leave the poor girl alone and let her play Words With Friends in peace.