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What does he like? I always get in trouble with my girlfriend when I buy toys. I recently bought a Nokia 3650, and in order to convince her that it is "cool", I showed her features that she would be interested in. Like how she can take pictures with the phone, email people and send pictures as attachments, browse the web for news and horoscopes, etc. She would never buy that phone on her own, but now she accepts it because of its functions. She now can use it whenever she wants to. (Not my choice)
To convince him that YOU need it, you must convince him that HE needs it.
Is he the frugal type? (Is he cheap? :p) Show him that its on sale, and theres free shipping, and these prices won't last long... Show him how much cheaper it is than comparable models of different brands.
Does he like to surf the net? I moved up from a Palm IIIx so I had no idea that PPCs were even capable of connecting to the internet, among other things. Let him know it can be done! If you don't yet have a wireless LAN in your house, that will require separate convincing.
Maybe you could tell him that he could listen to music and watch movies on it. This would be a good arguement if you guys are on the road often. If not, then he would counter that with "but we can already listen/watch on our stereo/TV."
If he likes to read, the previous point can also be used with books/eBooks. Make sure you emphasize quantity as well as quality. "The screen is big and bright so you can read wherever you go. I couldn't do that on my old Palm. Plus, you can have literally hundreds of books on it!"
If all else fails you could always try Plan B: "Valentine's gift", "can I buy it then return it after we try it", "it's more efficient and easier to carry around than my appointment book and calendar and notepad", "I need it for work", "I've been saving up for it"...
These reasons are in no particular order. Determine what features he would like, them arrange them accordingly. I would put them in the order of: best feature, low price, 2nd best feature, and go from there. Don't go to Plan B unless you've exhausted the main points. All right, good luck!
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