Let's get judgmental.
Occupation: Real Estate Agent
Can he win?: Yes. Real estate agent is one of the top 10 Bachelorette jobs.
Occupation: Information Systems Supervisor
Can he win: Yeah. This is one of those jobs that it doesn't matter if anyone outside of your workplace understands it as long as they know you're paid well to do it.
Occupation: Education Software Manager
Can he win?: You didn't really think you were getting out of this without meeting a software manager, did you?
Occupation: Aspiring Drummer
Can he win?: A 31-year-old aspiring drummer is the perfect joke to undermine the prestige and achievement-orientedness of these jobs. Kudos, The Bachelorette. You're really good at this. He's not supposed to win.
Occupation: U.S. Marine Veteran
Can he win?: Yes. And he's the only vet this season, which increases his chances even more. Also it's very, very funny that The Bachelorette has two Blakes on one season. I'm surprised that hasn't happened before.
Occupation: Male Model
Can he win?: Remember last year, when Daniel was originally described as a "male model" and then partway through he got changed to "Canadian?" I wonder what Brady's true identity is, other than "guy who won't win The Bachelorette."
Can he win?: Sure, that's doctory enough.
Can he win?: Yes. Firefighters are sexy (applaud my restraint for not saying "hot").
Occupation: Startup Recruiter
Can he win?: There's no reason a startup recruiter couldn't win, but Dean won't win because he already told Rachel "I'm ready to go black, and I'm never going to go back."
Occupation: Executive Recruiter
Can he win?: Uh, yeah, sure. It's more like his job doesn't disqualify him.
Occupation: Personal Trainer
Can he win?: Yes. Kaitlyn's winner Shawn Booth was a personal trainer, and still is, kinda. This franchise loves personal trainers almost as much as veterans.
Occupation: Executive Assistant
Can he win?: No. The fact that he's not already an executive proves he's not ready.
Occupation: Emergency Medicine Physician
Can he win?: Hell yeah, dog.
Occupation: Consulting Firm CEO
Can he win?: Sounds boring but lucrative, so yeah.
Can he win?: loooooooool this guy's name is Jack Stone? Is he an attorney or a character in an action movie? I don't see this guy winning.
Occupation: Sales Account Executive
Can he win?: Yes, but why can't there ever be like a professor or a novelist or something? Why does every contestant have to be a salesman?
Occupation: ER Physician
Can he win?: Does the Pope you-know-what in the woods?
Occupation: Tickle Monster
Can he win?: According to Chris Harrison, being a doctor is what this guy does, but a tickle monster is who he is. According to me, a doctor can win The Bachelorette, and a tickle monster cannot.
Occupation: Prosecuting Attorney
Can he win?: Rachel's a defense attorney. A prosecutor and a defense attorney falling in love? That's a sitcom, not a reality show!
Occupation: Senior Inventory Analyst
Can he win?: Sorry, Diggy. Unless your personality is incredible, that job is just too boring to get past. At least you have a cool nickname.
Occupation: Pro Wrestler
Can he win?: He's going about it all wrong. There's a template for pro wrestlers on dating reality shows established by I Love New York's David "Punk" Otunga: first you get a degree from Harvard Law, then you come in third on a dating show, then you get engaged to Jennifer Hudson, and then you become a pro wrestler. If you don't do it just like that it'll never work.
Occupation: Marketing Consultant
Can he win?: He won't make it past night one.
Can he win?: There's always a country singer. It's kind of weird how much The Bachelorette loves country singers. Chris Harrison said this guy's an "instigator" and pretty much spoiled that he's the season's villain.
Can he win?: Lucas will Whaboom his way right into a Week 3 exit.
Occupation: Construction Sales Representative
Can he win?: Yeah, but only if he never sells another backhoe ever again after this.
Occupation: Former Pro Basketball Player
Can he win?: UH NO DOY. Bonus points if he's a famous basketball player's estranged younger brother.
Occupation: Hotel Recreation Supervisor
Can he win?: Mmmmm, I'm gonna need a little more info before I can make a call. Is he, like, the guy who books DJs at hotels in Vegas or is he the guy telling teenage lifeguards to stop flirting and start watching the pool?
Occupation: Product Manager
Can he win?: Yeah, sure, who cares.
Occupation: Law Student
Can he win?: In a room full of practicing lawyers, a student. This guy is going to have a miserable time.
Occupation: Business Owner
Can he win?: WHAT KIND OF BUSINESS, PETER? WHY ARE YOU BEING SO SECRETIVE? WHAT ARE YOU TRYING TO HIDE?
Occupation: Sales Manager
Can he win?: They couldn't come up with something more interesting than "sales manager" for Will? Will won't win.