You don't have to buy phones from the operator unless you're using Sprint or Verizon. He's on T-Mobile which means he can buy a handset direct from their maker or a reseller.

I'd recommend sticking with T-Mobile if possible. I'm a little biased since I'm grand-fathered in on way crazy cheap data plans, but they are the most agreeable about letting you bring your own equipment.

There are a lot of options depending on budget. The Nokia 8800/8801 is a svelte, luxurious handset without a lot of overhead. They are on the expensive end for a lot of people that are used to getting The Free Phone, but not at all unreasonable considering all the factors.

I'm a bit of a smartphone whore -- I love Nokia S60 devices and UIQ devices from Sony Ericsson. I'm not especially impressed or interested in Palm devices, but the BlackBerry will always be interesting to me.

The MOT PEBL is a nice little clamshell that people seem to like, but I've never used one. Again, the smartphone bias. I think you can get one of those from T-Mobile direct, but I don't know what they do to it, or if it supports iSync via Bluetooth or if you have to cave-man it.

The Sony Ericsson K750i is a great little handset. It has some of the bells and whistles you're not interested in, but they're really great little handsets. They have good call quality, and a nice UI. My K700 is its big brother, and it does make a power-down bloop, but an officemate has a K750i and I'll check on it tomorrow.

Most Sony Ericsson devices throb when you plug them in, but the display light doesn't come on. I suppose the easy solution for any device that makes too much light is to either turn it off or put it upside-down or in a case. Or move your charger to the bottom shelf of your nightstand if that is what you're concerned about.

The Walkman phones from Sony Ericsson are almost entirely good. I don't like the design and branding but that is me being weird. They're music-oriented devices and you may be surprised at how nice it is to have a backup music player when you're sitting in a doctor's office and she's got 15 people ahead of you. :P

If you would be interested in a nice in-between, the Sony Ericsson M600i is a smartphone (UIQ) with an integrated thumbboard for messaging and email, but lacks a camera. That one lacks WiFi compared to its more full-figured sibling, the P990i.

The Sony Ericsson phones will almost always allow you to do the cool SMS/Call/Answer thing from Address Book. Symbian handsets from NOK do not, and it really drives me batshit that this killer feature doesn't work on S60 handsets :P

T-Mobile has a nice return policy I bet. If you wanted to try out the 8801 they carry (I think they charge too much seeing as how you can get them unbranded/unlocked for around USD$400 -- which is always the prefered way to go) and the things T-Mobile may or may not have done to it don't bug you, keep it or find the untouched version.

T-Mobile usually doesn't cripple handsets. Two of my BlackBerry devices are T-Mo, two or three of my Nokias are/were, and a MOT V70 was purchased without any apparant beatings from the T-Mo folk.

Sprint and Verizon are the most likely ones to do that shit because they are walled-garden posterboys.