How do I convince him our ages and jobs won't be an issue?

There's this guy, who is a Marine, and is also a line cook at the same restaurant I work at (we're both line cooks, just on opposite ends of the kitchen). He's mentioned thinking of getting a different job and/or going back on active duty sometime soon, and I only work at the restaurant two days a week (I'm at college the other five), so we're in that gray area of the don't-date-a-coworker rule.

He's also 5 years older than me (I'm 19, he's 24). However...due to financial reasons, he's in a typical 21-year-old situation (not enough money for an apartment, cheap car, etc), his friends are getting engaged and he doesn't even have a girlfriend, stuff like that. And I've always been told I'm very mature for my age anyway...

So how would I get him to consider dating me even though I think he may have a problem with the age difference and work situation?