Fascist-in-training Rolfe is a telegram delivery boy who flirts with Liesl. He seems like a nice enough boy at first, and it looks like he and Liesl are headed toward hot and heavy romance. In the charming duet "Sixteen Going on Seventeen," he offers to share with Liesl his worldly advice on matters of love.
ROLF: You are sixteen going on seventeen.
Fellows will fall in line.
Eager young lads and roués and cads
Will offer you food and wine.
Totally unprepared are you
To face a world of men.
Timid and shy and scared are you
Of things beyond your ken
You need someone older and wiser
Telling you what to do.
I am seventeen going on eighteen.
I'll take care of you.
It doesn't seem to matter to Rolfe that he's only a year older than Liesl. Maybe this is a subtle warning that he thinks a little too highly of himself and might be susceptible to people who make him seem powerful. Sure enough, his interest in Liesl goes on the back burner after the Germans invade and he becomes involved in "more important matters"—that is, being a loyal assistant to the local Nazi party.
LIESL: Rolfe! I'm so glad to see you. It's been so—
ROLF: Good afternoon. Give this to your father as soon as he's home.
LIESL: He's on his honeymoon.
ROLF: I know.
LIESL: You do?
ROLF: We make it our business to know all.
LIESL: Who's "we"?
ROLF: See that he gets it. […] It's a telegram from Berlin.
LIESL: Don't you want to deliver it yourself?
ROLF: I'm occupied with more important matters. And your father had better be too.
Captain von Trapp refuses to believe that Rolfe has gone completely over to the dark side. When Rolfe comes upon the von Trapps hiding in the abbey, the captain tries to convince him to run away with them, insisting that Rolfe isn't really like them.
And it turns out, the captain is right… kind of. Even though Rolfe threatens to shoot the captain, he doesn't. In fact, he lets the captain get close enough to disarm him. He's clearly scared, far from the hardened Nazi soldier he's pretending to be. He even lets Maria and the children go. You can practically see the angel and devil on each shoulder.
However, the captain ticks him off when he says that Rolfe will "never be one of them," and he alerts the rest of the search party that he's found the von Trapps. When he blows his whistle, it's the scariest sound in the whole movie.
Being allied with the Nazis is now giving Rolfe the sense of manliness and authority that he seemed to need back when he was courting Liesl and sang that she needed "someone older and wiser, telling [her] what to do."
We're not sure what we're supposed to think of Rolfe's fate. Since he went from bossing around teen girls to joining the Nazis to feel like a man, it doesn't look like he's going to end up in a great place.
Our verdict? Worst. Boyfriend. Ever.