Comedian Todd Barry has played Mickey Rourke's boss, a bongo-player, and a friend of Louis C.K.'s who thinks that Louie's mom bathing in a tub full of hobo diarrhea would make good television (he's right). But in anticipation of his five-show run at Caroline's this weekend, we figured we'd mine his experience of 28 years living in New York City for practical advice on first dates, finding money, and subway etiquette.

The following questions are real dilemmas and were argued by actual human beings until now, when Todd's peerless sagacity will silence any further debate. Behold:

A friend of mine asked me to help him move out of his apartment, but a few days earlier he told me he had paid for movers. I had stuff to do, so I told him that I couldn't help him, but he's been pissed at me since. Am I supposed to help someone move even though they've paid for movers?

I was going to say, “That’s like asking for a ride to the airport after you’ve already called 666-6666,” but then I realized it’s not like that. Your friend is trying to combine the efficiency of professional movers with the “I don’t have to pay you” aspect of asking a friend to help. What he’s not thinking about is that these movers probably have their technique down and your “help” will actually slow down the process. Mixing professionals with amateurs is never a good idea. It would be like if I did a show with a band, and insisted on sitting in on the drums, even though they already had a drummer.

Is taking the Staten Island Ferry a good idea for a first date? Some of my friends who've done it before say it's fun and low-key, but I'm not sure she'd be cool with making public transportation a first date destination.

The Staten Island Ferry is a great idea for a first date, as long as that ferry is headed to STATEN ISLAND’S HOTTEST “SMALL PLATES” RESTAURANT!

Is it wrong and touristy to take photos or video of weird/gross things one sees on the subway? Like fights or camel toes or guys licking their shoes?

If I saw a guy sneaking a photo of a woman’s camel toe, I don’t think my first reaction would be, “Hey, that guy’s being touristy. Is he going to look at that picture while he’s shopping at the M&M store?” Don't take pictures of people on the subway.

After my friends and I had finished dinner the other night, I had to duck out to get cash. I went to an ATM in a bodega and found a $20 bill sitting in the bin, so I took it and used it to take $20 off the total bill as a way of sort of "paying it forward," for a lack of a better term. My friend says I was wrong, and should have turned it into the bodega clerk. Should I have turned it in?

Why would you turn the money into the clerk when you can “pay it forward” by helping your friend save 50 cents on a plate of Orecchiette? Seriously though, I think you should’ve left the $20 in the bin, on the off chance someone came back looking for it.

The window in my bedroom overlooks an enclosed courtyard that acts as a trash area for an adjacent apartment building. Every Sunday at around 12:30 a.m. the super for that building dumps all of his recycling out of the bins and into cans to be placed out on the street, making a huge racket for at least 20 or 30 minutes. Sometimes he's drunk—I can hear him yelling at the trash, or yelling at someone upstairs, or just making strange noises in addition to all the clattering and clinking of empty bottles. Sometimes I can sleep through it but mostly it drives me insane. Is there anything I can do? Should I try to ask him to take the trash out earlier, or am I just stuck with this until I move out? I've talked to neighbors in my building who say it keeps them up too.

This happens every Sunday at 12:30 AM? So basically, late Saturday night? What kind of building do you live in where everyone is home on a Saturday night? CAN YOU POST THE ADDRESS OF THIS BUILDING SO FUN PEOPLE LIKE ME WILL KNOW TO NEVER MOVE THERE?! You wouldn’t hear the super’s racket if you were OUT ON THE DANCE FLOOR WHERE YOU BELONG!

Someone is taking up a subway seat with their bag, and it's the only seat available, what do you do?

I had a very similar situation today at a coffee shop on Spadina Ave. in Toronto. There was only one seat available, but a woman had her purse on it. I came up with this line on the spot: “Is anyone sitting here?” She moved her purse and I sat down. That’s not a great story, but it’s a true story, and it answers your question perfectly.

What foods should you avoid eating on the subway?

The only thing I eat on the subway is crème brûlée. People really love it when I pull out the torch.

You can buy tickets to one of Todd's shows at Caroline's this weekend here—the first show is Friday at 8 p.m. Or pick up a CD or DVD of his latest special, Super Crazy, here. Or read him eviscerate an interviewer in 2004 here.