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I spent yesterday afternoon immersed in a modern-day holiday tradition — helping my parents shop for their first smartphones. Three hours after we arrived at the mall, they each walked away with an iPhone 4. But the most interesting part, to me, was my unsuccessful attempt to convince my mom to buy a Windows Phone instead.

Here’s the story: My mom was the key person driving this purchasing decision. At 73 years old, she has become an avid texter, but she has been texting in the style of a teenager circa 2006, using the numerical keypad on her standard-issue cell phone. Not ideal, to say the least. Initially our plan had been to make a more modest upgrade, getting her a simple phone with a slide-out keyboard for texting.

But as we were talking it over the night before, she decided she wanted a smartphone instead. My mom listens to our GeekWire podcast, so she recently heard our 97-year-old Geek of the Week Bill Sleeper pitch the benefits of smartphones for seniors, and that seemed to influence her thinking.

As long as my mom was taking the leap, my dad decided that he would, too.

As first-time smartphone buyers with Windows 7 PCs at home, they were in many ways Microsoft’s perfect target customers. Also, I admit, there was a bit of an ulterior motive behind my Windows Phone pitch. I envisioned doing a series about my mom and her Windows Phone, similar to the Surface Diary in which I persuaded my wife to spend our iPad budget on one of Microsoft’s new tablets.

So after we walked into the first store and put our names in to talk with a sales rep, I went over to the Windows Phone display and showed my mom the new HTC 8X Windows Phone, which is my favorite of the new Windows Phone 8 devices. It’s sleek and light with a colorful, curved backside and a bright screen. I really think this is a nice phone, so it wasn’t tough for me to make the pitch. I showed her the Windows Phone live tiles vs. the comparably boring and static screen on my iPhone.

But as it turned out, it wasn’t much of a pitch, because my mom wasn’t really interested in listening. Her first objection was predictable: She was concerned that it wouldn’t have the apps she would want. (She has been listening to our podcast more closely than I realized.)

Were her concerns about apps valid? I explained that all the basics are there on Windows Phone, and then some. We didn’t discuss this until later, but a good example for my mom is the Kindle app for Windows Phone, letting her access her books if she happened to leave her Kindle at home. On the other hand, I also suggested that my mom use Stitcher to stream her favorite podcasts, rather than download them manually, and that app isn’t available for Windows Phone yet.

But as we talked about it more, the bigger issue for my mom was the familiarity of the iPhone to the people around her. If she needs help figuring something out, she can turn to one of her friends or one of my sister’s kids, who live in the next town over and all use iPhones and Apple devices.

“It’s a known quantity,” she said.

At that point I gave up. As I told my dad, it’s a new spin on the old saying about IBM: Nobody ever got in trouble for letting their parents buy an iPhone. Of course, all of this speaks to the larger challenge that Microsoft faces in the world of smartphones and tablets.

The other hurdle was that the HTC 8X was on sale for $99, but my parents were each able to get an iPhone 4 for free, although they still had to pay sales tax, which added up to about $60 total.

(Side notes for anyone else who does this with your parents: If one of them is a veteran, check with their wireless carrier to see if they can get a discount on their monthly bill. Also, the way the sales reps explain data limits, storage capacity, monthly plans, etc., is still way too complicated, to the point that I felt like I was translating a foreign language. Huge need for improvement here.)

Back at home, this morning, my mom had me show her how to set up her contacts and text with her friends. Since it’s the device I use every day, it was quick and easy for me to walk her through the basics. She has already sent five text messages this morning, and counting.

“I’m so glad we got this!” she said, saying it’s something she’s thankful for today.

Happy Thanksgiving, everybody — no matter which phone you happen to choose.

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