Sometimes boors are unstoppable, but you might try, for the lunch thing, after the name calling, saying. "That's not funny anymore." Repeat no matter what he says in reply. Say it very unemotionally.

During that afternoon walkies, reply to him with "That's too bad. I have to get back to work" and turn away. Or, you could say what a coworker of mine used to say: "We're not here for love."

It sounds like he's a little OCD. I'd suggest gentle teasing -- e.g dramatically hold up your hand and say "Stop! Its coming to me . . . what you're going to say . . . I don't know how I know this . . .you're going to ask me if I brought enough for everyone!"

or -- say, "Yes. I can now wave my pencil and make my lunch reproduce. How many copies of it would you like?"

Just break this pattern up yourself by being unexpected in a friendly way. He's stuck, but you don't have to be.

Alternately, just ignore it the way you do all the other repetitive sounds of your life (traffic, garbage pickup, computer boot up sound . . .)

How about answering him bizarrely and unpredictably?

HIM: "What did you bring for lunch today?"

YOU:
-Elephant eyeballs in monkeybutt sauce
-Kippers and toad in a hole
-A bag full of annoying questions
-Your grammy's pajammys
-A big bowl of Nunya
-A stinky, runny cheese crawling with maggots

...make them obnoxious enough and maybe he'll stop asking. Or at least, take the spotlight away from him.

Sounds like an anxiety issue. He wants to start a conversation but doesn't know what to say? I don't know; I don't know the guy.

Ask him if he's hitting on you. Each time.

Introduce the word 'annoying' out there in the best humor possible.

If he doesn't get the picture, or barrels on anyway, then you can just upright call him annoying to his face.

And if it turns into him deliberately being annoying, and you telling him he's annoying over and over, well, at least now it's being played in the open.

I like Miko's idea.

You guys are hilarious - We're not here for love! Monkeybutt sauce! HA! With winter approaching, I'll be cooking at home and bringing my lunch more, so I look forward to trying out some of these suggestions.

For me, the best way to fend off recurring annoying questions is to ask some of my own --- questions, that is. I was about to say "I hope they're not annoying!" but then I realized that in this context, I don't much care if they're annoying, so long as they're civil and effective.

I used to have a classmate who made the same not-joke ("Did you bring enough for everyone ahahaha?") every damn day during the lunch break in a long class. So the bazilliontieth time he asked, "What did you bring for lunch?" I might answer:
- "[whatever delicious dish I made], do you ever make that at home?"
- "[thing I picked up from the store], I [love/hate/] that place. Where do you grab lunch?"
- "Oh, same old thing. How's your [kid, partner, home, hobby, project] going?"
and so on. I just make a tiny effort to re-channel the conversation into something that doesn't bother me as much.

Often, people really are just trying to make a connection but don't know how. Sometimes, I find this small effort on my part makes a big difference in how the conversation goes. (Aaaaand sometimes, a person is the same annoying goof no matter what. Oh, well.)

... but once I did bring in enough for everyone. He'd been making a fuss about my roughly sliced home-baked oatmeal bread, talking about what a crunchy-granola whackadoo I must be to bake bread routinely (and, y'know, he's not wrong), and other classmates ad asked me some basic baking questions. A week or so later, I brought in a sliced loaf of fresh-baked bread, some butter, and some cheese, enough for everyone in the class to have a slice. My classmate stopped making the "Did you bring enough for everyone" joke around then.

Instead, he started asking me when I was opening a bakery. Sigh.

As my mom would say, "He's just saying that to hear himself talk."

Ah, phatic speech. What he really means is, "I am here. I exist. Acknowledge me."

That's all. Nod and smile. If that's the most annoying thing that happens in your workday then you work in paradise.

Man, one day I would just bring enough for everyone and say "Yes, yes I did. I hope this settles the matter."

I have a friend who answers every unwanted question: "Why? Are you a cop?"

"Why? Are you a cop?"

I am so using this on my friends this weekend. You and jessamyn have me cracking up.

My first instinct would be to respond "Bullets. I brought enough for everyone." but I know that would bring me trouble so I would just fall back to my unwanted question standby "Why?"