Five iPhone Dating Horror Stories That Will Make You Glad You Don’t Have A Date This Valentine’s


Has your iPhone ever caused trouble between you and your significant other?
Has your iPhone ever caused trouble between you and your significant other?

iPhone use and dating don’t really mix very well. Even if you follow our Gentleman’s Guide To Using Your iPhone On A Date, you’ll still probably do something really dumb if you try to pull out an iPhone on a date. Their feelings might get hurt. Heck, your feelings might get hurt. You’re both going to walk away more sexually frustrated than ever. It’s a bad idea.

Yes, there are apps out there that can help you get some action on Valentine’s Day, but the regular apps on your iPhone are probably going to destroy the hard work you put in.

Here are five stories that should encourage you to just leave your iPhone at home on Valentines Day.

Siri Ruins a Date


For their first date, Jon and Keri decided to meet up in Philadelphia and take a walk through the park. Things seemed to be going swell, but then Jon got a little too eager to show off the new iPhone 4S that he recently bought.

When trying to figure out which wine to choose, Jon consulted Siri, and then grew erratic when Siri couldn’t understand his request.

“Siri, I will run you over in my fucking car if you don’t suggest a good wine.”

I cut in, “Maybe just open up a search engine and look some of these wines up?”

“I shouldn’t have to do that. What am I paying over a hundred bucks a month for if my personal assistant can’t even assist me in picking out a good wine for me and my date?”

Jon excused himself to try to go fix his iPhone, while Keri ordered a glass of wine, downed it, and quickly left the restaurant for the night. Where did Jon go? He headed on down to the Apple Store to try to get Siri fixed, and seemed actually startled that Keri had decided to call it a night.


A Photo Album of the Competition


Weird iPhone dating habits don’t just afflict men. At the very beginning of Jan’s date with Molly she handed him her iPhone which was opened to an album called “Da Guyz!” Jan scrolled through the photos and saw picture upon pictures of dudes he didn’t recognize hanging out with Molly.

“Who are they?” I asked her.

“Guys I’ve dated,” she replied, “Just thought you’d want to see.”

I handed it back to her and asked, “Is it my turn, now, to show you an album of women I’ve dated? I didn’t make a special album, but I can show your their Facebook profiles.”

When Jan didn’t thank Molly for letting him see his competition she called him an asshole and the date was over.


An iPhone Full of Sawdust


Dealing with a water-damaged iPhone sucks. You can try shoving it in a bag of rice for a day but that doesn’t always work. Kendra dropped her phone in the toilet right before her date with Ricardo. Without any rice on hand, she decided to put it in a freezer bag full of sawdust, throw that in her purse, and then head to her date.

Richardo says that other than her sawdust covered sweater, Kendra looked good. They ordered appetizers, and once they were delivered, Kendra’s phone started ringing nonstop…

Her phone rang again. She took the entire bag out of her purse and squeezed it all over, apparently trying to locate the silence button/switch. When that didn’t work, she groaned and slammed the bag against the table until it burst, making me jump and spraying sawdust all over the table, herself, and into my soup.

She looked up at me and said, ‘Your own fault for getting soup.’

Dinner was otherwise uneventful, but it was the couple’s only date. 


 Siri Can’t Keep a Secret


Tom was quite inebriated when he asked Emma out on a date. In fact, he wasn’t even sure that her name was Emma, but he guessed it was, so he put the info of their planned date into his calendar and left it at that.

Once they met up a few days later, Tom found out that Emma’s name was actually Sarah, which didn’t seem like a big deal at the time. Sarah said she was interested in technology, so Tom whipped out his iPhone 5 and they played around with Siri a bit and asked her questions. Then Sarah asked one question too many to Tom’s iPhone.

Sarah: “Siri, what am I doing today?”

Siri: “OK, here’s your event”

And there it was: “Date with Emma”. That was it… She went. Gone. Forever. With tears in her eyes. I was speechless.


Find My iPhone Saves the Date


For all the horror stories we hear of people using their iPhones on dates, sometimes it can pay off in a big way. At the end of Adam’s date with a lovely lady, they were hanging out by her car doing that awkward dance where you’re not sure if you should go in for the kiss or not.

While the sexual tension rose, some guy with a gun jumped out of the shadows and demanded all their valuables. Adam handed over his wallet. The girl gave the thief her purse and rings.

And then I thought, ‘All right, well at least he didn’t ask for my phone.’ But then he asked for my phone, which turned out to be a very good thing.

After the crook ran away, Adam pulled his iPad out of his car and used it to help the police track down the thief using Find My iPhone. They capture him 30 minutes later and recovered Adam’s wallet and his date’s purse and rings, proving that sometimes it pays to be a fanboy.