I'm a prime lens guy, as the image quality is superb and the fixed focal length forces you to be more creative with your shooting... I'd avoid the zooms, but your mileage may vary.
IMO, going the macro route on a 550D is the best option... You may find you like doing closeup work, and then it becomes two lenses in one. Before I went crazy and did full frame, I used my 50/1.8 and my 100mm macro (non-L) for portraits. You can get a fair bit of background blur with the 100mm wide open given enough distance between your subject and the background, and the minimum focusing distance isn't an issue if you want to get close to your subject. The 85/1.8 is great, but it's definitely a one-trick pony and if you're trying to get the best bang for your buck, you probably want to look elsewhere... The 100/2 also fits this description as it's essentially just a longer 85/1.8.
I'd definitely avoid the 60mm macro, it's just not an exciting focal length IMO and the 50/1.8 can do portraits on the cheap, plus it's full-frame compatible... Much better value, IMO.
All of the following on a 450D and with the 100mm non-L macro.
Macro on an engagement shoot:

Portrait-type shot:

Bit of silhouette stuff:

Close-up portrait:

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Canon EOS 5D MkII | Canon EOS 7D | Canon Digital Rebel XSi | EF 35mm f/1.4L | EF 50mm f/1.8 II | EF 85mm f/1.8 | EF 100mm f/2.8 Macro USM | EF 135mm f/2L | EF-S 18-55mm f/3.5-5.6 IS | 580EX II | LumoPro LP-120
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