Honestly it depends largely on you and what you prefer. Around the city I'd avoid the big cruisers, but a small one (~600) can be nice if that's your thing. A standard bike is a pretty good way to go (not leaned back like a cruiser, not leaned forward like a sport bike).
My first (after college) was a crappy old '81 Suzuki GS 550L. What a brick. But it scooted me around for a year, and I sold it for $50 less than what I bought it for. Second was a '94 Honda CBR600F3. Fantastic sport bike. Pretty much a do-everything bike, and it was reasonably comfortable. Rode that thing all the way to Portland, Oregon (and around Crater Lake too).
After that I had a few other bikes, but bought a brand new 2000 BMW K1200RS. I still have that thing. 56,000 miles and it ticks like it's brand new. Amazing machine. I've ridden it every damn where (down to Phoenix and back up through the middle of Nevada was incredible).
For fun along the way I picked up a '94 Honda Magna and customized the heck out of it (made it a pretty slick looking bobber). That thing was great. But it was a 750 and not fast enough for me these days, so I sold it. Bought a 2004 Triumph Daytona 955i CE. Holy cows what a machine. I split weeks between the BMW and the Triumph now tearing up the road between San Rafael and Oakland where I work.
Wish I still had that Magna though. After I got done with it, it was a real looker, and darned fun to ride. Nimble as can be. Very low slung seat. Great balance.
I usually advise people to go sit on a whole bunch of bikes. New ones, old ones, even bikes you think you'd hate - you'll always learn something. Pay attention to how the bike feels under you. Understand where your feet go and how your back feels when you're on the grips. Keep in mind that a slight forward lean when riding on the freeway neutralizes the wind against your body. That's why sport-touring bikes (like my BMW) can be ridden for so long at a stretch.
When you think you know what style fits you best, go find a small to medium sized bike to start on. It can be old and beat up. And your friends can call it stupid or whatever. Don't give any craps about all that. Just get some bike smaller than a 600, and learn to ride it. Believe it or not 250s are terrific. I'm a big guy (6'2", 240lbs) and I'll ride a 250 all day long and then some. Someone make fun of me? I don't give even half a damn. 250s are fun as can be, they get great gas mileage, and they're easy to ride in an urban environment. Not so great on the freeways, but a great learning platform.
If you MUST ride on the freeways, I'd recommend something a little bigger than a 250. Maybe one of those new 300 sport bikes, or a 500-ish something standard. You want that extra power on the freeways.
Cost for a decent bike these days has gone up a little, but figure that if you keep the bike in good condition (cover it when it's parked - every time), you'll get a lot of your money back when you sell it.
'81 Suzuki GS 550L. Bought for $850, sold a year later for $800. '94 Honda CBR 600F3. Bought for $4300, sold two years later for $4000. '85 Honda Rebel 250. Bought for $1200, sold two years later for $1100. '86 Honda Rebel 250. Bought for $1000, got an insurance check for $1400 when it was stolen. '94 Honda Magna. Bought for $2000, sold two years later (customized) for $2800.
There have been some others. But I haven't lost much money on my rides. These days have a budget of $2000-$2500. Ya ya sure you can find bikes out there for less and there's always a friend or some guy who tells you about some bike he saw for sale cheap and baloney blah blah. But if you have a couple grand at the ready, you can get a decent ride and take it to a mechanic to make sure it's up to snuff. And that's a big deal. I'm 46 and I've got a little over 30 years of riding experience, and I was Director of Service for a major Porsche dealership (and Mercedes dealership, and Mitsubishi dealership, and a BMW motorcycle dealership), and I can say with some certainty that it's well worth your while to have a good tech check out a new vehicle.
When I bought my Triumph, I got it from some random dude way out in the middle of nowhere (I trailered it back from Waterford - east of Modesto). The guy I bought it from didn't know anything about the bike. So I rolled it in to the local Triumph dealership and told them to do a major service. Ya, that service was $2000, but I'm older and have money and the bike is a collector's item, and I ride it fast every day, so I figured it's money well spent. For a decent once-over, expect to pay about $150. If the bike needs something (it likely will), it might run you another $200. Bikes aren't all that expensive until you get way up in to the performance levels - ugh.
Sorry, I appear to be writing a book here.
Go look around. Sit on bikes. Learn stuff. Then, when you're about 75% sure you know what you want, go and get it. Don't over think it. It's a first ride. Learn to ride it. Then get your motorcycle license. Ya, it's a bit of a catch-22, but that's the way everyone does it. Sure you can take a class. Those are good. They cost money and take time and while good, they don't prepare you for much of what you deal with on the roads. If you've got the money and the time, go do the class. It's a good idea. I never did, but hey - I'm me.
Ride that first bike for about a year. Take good care of it, but if it gets a little messed up along the way don't worry too much about it. Then, after a year, sell it and buy what you want - by then you'll know.
Make sure you get a good helmet. My first helmet was literally a 'came-with-the-bike' thing from the early 1980s. Wow what a can. Made me hate riding - even in the city. Once I stepped up to a Shoei things got good. Then I bought an Arai - and I've never looked back. A good helmet makes a huge difference. There are lots of good ones out there these days. Don't be a brand snob - go try a lot of them. I'd avoid Bilt, or some of the other bottom-of-the-barrel brands, but AGV is good (Rossi knows what he's doing) and there are some others.
Get a good jacket with a zip-out liner too. The textile (cordura / non-leather) jackets are good, but if you ride fast they tend to be loose and flap and lot. That's annoying. There are some leather jackets out there which are good and not too expensive (I read Joe Rocket has a good one). And get a good set of gloves. Make sure you try on the gloves before you buy them - no mail order. I've made that mistake more than once.
And then just go ride. Be careful - far more careful than you think you need to be. And if you're riding with a group who wants to do things you don't feel safe about, to Hell with them - stay safe. I once told a motorcycle club full of millionaires from San Francisco to get bent because they wanted to carve up the Marin County back roads at stupid speeds. Can I do that? Ya, I ~can~ do that. But I prefer to take it easy out there and I give no damns about what those millionaires think of me. And there will be plenty of stupid kids on hot bikes wanting to bolster their self-esteem by getting over on you. Give no damns. Don't take those idiotic risks. I ride bikes which can go faster than most of the bikes those idiots can afford - and I let them pass me all the time.
(Oh - pro tip: When splitting lanes, it's great to have a bike in front of you to 'part the waters', so to speak. If some A-hole wants to go faster between cars, then let him - he'll make the hole and you can comfortably ride in his wake.)
Okay, enough of all this. Let me know when you get a bike.
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