In any case, I do think that much of this comic feels more appropriate to a ten-year, rather than a five-year reunion. Acting careers can spike as rapidly as Sara's seemingly has, but most others (such as fashion) take years post-college to actually become a known presence in, unless you happen to win a reality show competition on Bravo. The fashion angle actually bugs me LESS than that, simply because, as T notes, fashions often move with surprising speed to somewhat absurd positions. I find it much stranger, honestly, that virtually everyone seems to have settled into their career paths and have an established significant other (both are currently trending later in life, not earlier, at least outside of the Deep South, where teen pregnancy is more endemic to shotgun weddings) than to see them wearing outfits that leave me scratching my head.
Nowadays most people are just picking a college at random and moving on with their career from there(since so far the comic has been unaffected today's economy, let's assume the economy is KICKING in 6 years). Fred as a PR guy doesn't strike me at all out of place, particularly since I know many guys that just went to PR school and instantly got well-paid jobs at some multinational(and one of them was organizing prett important events when he was 19). Then again, I also met a chick who was a copywriter for Leo Burnett when she was still in highschool...maybe I just met the right people.
Daphne as a successful fashion consultant is directly related to Brandi's decision to endorse her. Being a new sport, it might not be too big, but enough to gather a small number of fans. Whether it will grow enough to become a viable future choice is debateable of course, but if that happens they're good; even if it stays a minor sport, it might still be good enough to support her. If it flops...well, Brandi'll think about that if that happens. Daphne's future is already boosted anyway and she has a good spot on her record, helping her out in the future.
Sara was good enough to be on a memetic show(as we are given to understand via the #hellyeah twitter tags), which can be a huge jumpstart. She also has a colaboration with a huge director under her name(no one has to know it was a failure of a show), so she can quickly gain at least a minimum of success in 5 years' time. Even if she doesn't become a celebrity, keeping to minor roles is good enough for a career.
Tharqa probably wrote a "how I lost 100pounds quickly" book and got a bestseller(that and the fact that these days the stupider the book the more it sells can also boost her success...or she can be just bragging with being published despite not having any success, which is why she's trying to get daph and sara close; it's not hard to get published, after all, and anyone can write).
Katy and Jack were going out for quite some time, and with Katy's Christian beliefs it shouldn't be a surprise that the marriage came early(where I'm from the really religious people get married before their twenties, if that's not true everywhere I apologise; still, going out for a while), and Jack is clearly not really sure what he's doing but is biding his time thanks to Stan. Stan was always charismatic, and was probably there at the right place and time and had the wits to recognize and opportunity and take it(or it might have been one of those many, many, many huge cash prizes handed out at Uni contests, if you want a more realistic way of getting money:P).
Shelly is doing relief work, but whether or not it's a viable career choice is debateable. She might have something else on the side but it just doesn't make that good of a story to tell at the reunion. We don't know what Duane does, but he always a lit enthusiast so it's not out of place to assume he kept on that road.
Just because people are bringing their girlfriends doesn't mean they're married or anything; they could be going out for a while, and there's nothing to stop people from bringing a new SO to the reunion if he/she feels like it. And anyway, they're what, 23-24 now? Most people are in serious relationships by then anyway.
So yeah, I don't find it that surprising. And I am totally loving Brandi. (and only after reading the comments did I realize that Bri is Fred's boyfriend, not Brandi's. I can be slow)