You Will Love São Paulo. Please? São Paulo, Brazil, is my second home. As second homes go, it's problematic: the city of 11 million is a grimy, dangerous megalopolis, as aesthetically pleasing as a bunion and harder to navigate than the Strait of Magellan. No one asks someone with a pied-à-terre in the Latin Quarter "Why do you love Paris so much?" Lots of people ask me "Why do you love São Paulo so much?" Including some people from São Paulo. My answer: it's a culturally sophisticated, pulsingly energetic, spectacularly social city with endless surprises and deep potential bubbling just below the scruffy surface. But when friends come to visit, aphorisms won't cut it. I have to show them why they should love the city. When Doug Mollenauer, whom I've known since sixth grade and still talk to weekly, tagged along on a speaking engagement I had in Rio de Janeiro earlier this month, I had 36 hours to show him my São Paulo - one that looks quite different, by the way, from the one filled with the glittery restaurants and luxurious hotels that the average business traveler (most visitors are business travelers) experiences. Doug would eat with the people and sleep on my couch - if I let him sleep at all. My trips back to São Paulo from New York rarely include an evening in. It didn't help that we were flying in after spending three sunny days in Rio, a place of such uncommon beauty that people have been known to fall in love with it between the airport and the hotel. As I plotted Doug's visit, I realized that the task of imparting your love of a place you know intimately to a friend just passing through was a quandary faced by many hosts. So I decided to have Doug write up the trip so I could see how I did. Beware traveling with a travel writer, lest you be assigned homework on vacation. I've reproduced his observations below, and tag-teamed with my own commentary, in italics: Doug: Flying low over the sprawling city of São Paulo, I could tell from the haze that my poor lungs would soon believe they'd landed in Los Angeles. Quite a difference from the several days of clear blue skies I'd enjoyed in Rio de Janeiro. São Paulo would truly be new to me. Even though I've been good friends with Seth for three decades and we know more about each other than most married couples do, I still didn't know much about his adopted city in Brazil. Sure, I had heard São Paulo was big and dirty, but that was basic stuff: I'd just confirmed both traits before my plane had even landed. We took a taxi from the airport and headed to Seth's neighborhood in central São Paulo. Accompanied by the smell of hot rubber and vehicle exhaust (an eye-watering blend I'd describe as "Mexico City, 2006") we drove slowly along wide streets named for Portuguese explorers and Brazilian revolutions, passing dozens of mid- and high-rise buildings that faced the main road like watchful sentries. Indeed, São Paulo is so chock-full of tall buildings you might think a platoon of Manhattans had traveled to Brazil and overstayed their tourist visas. Seth: Doug and I arrived midday, so that meant we could head straight for one of my go-to lunch spots, a pay-by-weight buffet where a colorful salad, rice, beans and meat with blended-to-order fruit juice costs me about 20 reais, or $10 at the current two-to-one exchange rate. I didn't comment when Doug committed a few pay-by-weight sins (loading up on cheap, heavy rice, taking way more than any normal human would eat). Doug: We ended up at Sabor e Arte on Rua Marquês de Itu, a buffet-style restaurant with a beautiful outdoor courtyard. For me, the word "buffet" usually brings to mind heat lamps and decomposing Chinese dumplings, but the food at Sabor e Arte was fresh and delicious. I loaded my plate with an American-size portion of fresh fruit, several entrees and a huge green salad. It was a lot of food for lunch, and not cheap at around 32 reais, but with my hollow leg cracked open I dug right in. Seth: Brazilians must have coffee after lunch, and I live near one of São Paulo's most famous residential buildings, which houses one of the city's great stand-up espresso bars. Doug: You'll find coffee on just about any São Paulo street corner, but Seth had a special place in mind: Café Floresta. The chain serves up fine coffee, but the real allure was this branch's location on the first floor of the famous Copan building. Designed in 1954 by Oscar Niemeyer, the Copan sits in the densely packed city center and looks like a 30-story cement sine wave, with its sunshades perched between floors bringing to mind an old car radiator grill. The brief walk from Sabor e Arte to the Copan required crossing under the "Minhocão," an elevated highway that serves as an unofficial border between "good" and "bad" parts of town. I didn't sense an obvious change after we'd crossed the dividing line, but I kept my eyeballs moving and gripped my iPhone a little tighter, heeding Seth's warning against showing the gadget in public. I first thought Seth's constant reminders smacked of traveler's paranoia, but he was backed up later when a woman on a city bus frowned and admonished me in English to "Put away your phone, it's dangerous." Seth: Every time I return to São Paulo I rather selfishly organize a welcome-back gathering for myself, and this time I planned it for Filial, a traditional "boteco" so Doug could get a sense of old-school waiters, chopp (draft beer with thick foam), local bar snacks and animated Brazilian conversation. Botecos, unlike American bars, encourage sitting around a table and talking. Not coincidentally, no nation produces better conversationalists than Brazilians; I've often said I'd just as soon drink with five Brazilian strangers than five American friends. Doug: Our last stop of the day was a bar-cafe to visit with Seth's friends and celebrate his latest return from New York. Sitting among expat writers and talkative locals, including one Brazilian named Marcelo who possessed an uncanny knowledge of "Seinfeld" and "Curb Your Enthusiasm," I downed plates of bar food, sampled caipirinha cocktails and drank ice-cold Brahma beer. The fried chicken, dried beef, fried veggies and other dishes weren't particularly inspiring, but the caipirinhas were laden with fruit, and the beer, served with a thick head and in small glasses (so it doesn't have time to get warm), went down easily. Too easily, no doubt, but it wasn't just my willpower that betrayed me: the waiters were like dancing magicians, using misdirection and sleight of hand to ensure my glass was always full. Sobriety simply had no chance. Happily, everybody at the table spoke excellent English, and the evening helped confirm my sense that Brazilians are a genuinely friendly and easygoing bunch. Seth: The next day, my idea was to give Doug a deeper sense of two contrasting sides to the city: We'd start with the old center, which despite some improvements is still more drug- than barista-infested, and then take a long bus ride south to the upscale area around the Parque do Ibirapuera, São Paulo's uncentral Central Park. Doug preaches the "get to know a city by running it" travel ethos and suggested running from the center out to Ibirapuera, an absolutely insane idea that I agreed to after realizing it was only 4.4 miles between two sections of town that to local Paulistanos were worlds apart. But we started with the 50-foot walk to one of my favorite spots in town: the breakfast spot next to my building. Doug: We stopped at Confeitaria Little for a late breakfast of espresso and pão na chapa, or grilled bread with butter. I didn't expect much from a dish so simple it could be on a prison menu, but opa! it was darn tasty. Seth munched on his favorite, a guava-paste croissant. At my urging, we organized Day 2 around a run. Despite São Paulo's limited green space and lack of respect for nonmotorized travel (I recommend having your personal affairs in order before stepping off a curb) I was confident we could carve out a decent route. A quick Metro ride from Seth's and we were at Rua 25 de Março, a bustling outdoor street-market filled with hundreds of ambling shoppers. Next, we visited the Mercado Municipal Paulistano - the São Paulo Municipal Market - an immense, neo-Classical building that houses an expansive indoor food market. I'm not a hard-core foodie, but I knew my chef wife would have fallen for the "Mercadão" the instant she walked through the door. We ordered the classic specialties: a thick mortadella sandwich (11 reais) and salt cod in fried pastry (12 reais) at Famiglia Rivitti, one of many stalls: We also dropped 10 reais on off-season jabuticaba, a delicious, grapy fruit with a soft, litchi-like pit. We still had a run to do, so we ate only a few bites and packed the rest of the food into Seth's backpack. After a visit to Estação da Luz, a beautiful 19th-century train station with high ceilings, intricate ironwork and narrow walkways that could easily have been the body double for Gare Montparnasse in Martin Scorsese's movie "Hugo," it was time for our urban ninja run. We headed south, dodging traffic, bus fumes and disbelieving stares. At one point, a group of people shouted from a cafe across the street: were they cheering us as heroes or mocking us as fools? Impossible to say, but this was clearly something they didn't see every day. Seth: The run was a bit brutal - but I'll hand it to Doug: it was also a great way to get a sense of the city center. I knew Doug would love ending in Ibirapuera, and I tacked on a first-time visit to the MAM, or Museum of Modern Art. Which turned to be free that day but is usually 5.50 reais. Doug: It took nearly an hour to make our way to Ibirapuera but it was worth the effort. Around us, runners, bikers and skateboarders were taking advantage of smooth paths around the lake, striding and rolling past fountains and more Oscar Niemeyer-designed buildings. I did a few more laps before stopping to buy a bottle of coconut water from a vendor. Is Ibirapuera as nice for running as Rio's Lagoa, with its views of the water, Sugarloaf Mountain and Christ the Redeemer? Heck no, but for gritty São Paulo, it's a godsend. After our run, Seth and I walked over to the Museum of Modern Art, to see what culture we could sponge up in the hour before it closed. The current show was "At the Margins," a creative yet disturbing exhibit by the Brazilian artist Adriana Varejão. If you can imagine human entrails spilling from tiled walls and world maps, you've got a decent picture of Ms. Varejão's art. Seth: I frequently just snack at home for dinner because of how expensive São Paulo restaurants are. The city is proud of its pizza, for example, but the best versions come not in folded $2 slices but in $30 pies eaten with knife and fork. But when need be, I frequent an always-bustling bistro where quiche served with salads cost 25 reais, and a bottle of wine can be had from an incredible 30 reais (though I favor the 40-real syrah blend, still an absurdly cheap price). The waiters - and the crowds - never change, nor does the charm. And from there I'd force Doug to keep the party going at a downtown nightclub where three friends were guest D.J.'s. Doug: It was time for dinner by the time we returned by bus (3 reais), and Seth's choice was La Tartine, a cozy French restaurant known for its affordable quiche and salad combo. The place was busy, yet we were able to sit right away, and it wasn't long before several sizzling slices of quiche (25 reais) came our way. It was as tasty as it was frugal, and we wet our whistles with a nice, midpriced syrah to add to the fun. Speaking of fun, La Tartine also seemed to be a fine spot for romance, as evidenced by the couple furiously making out behind us. Brazilians, I noticed, dig kissing in public. Last stop on the São Paulo tour: Alberta 3, a hip nightclub where Seth's friends were spinning American and European pop music: the Clash, Phoenix, the Strokes and the Smiths were all in rotation. It was a taste of home, and I did a fair amount of jumping around despite my sore quad muscles. We stayed late (too late for a 42-year-old guy with a 7:40 a.m. flight) but we ultimately made it back to Seth's for a few hours' rest. Seth: Doug had humored me by putting up with all suggestions and forgoing sleep to see as much of my city as two pretending-to-be-young old friends possibly could. Would he go home and rave to his friends about São Paulo? But at least he'd know why I do. Doug: It's not easy, nor particularly fair, to assess a city based on 36 hours, but I did come away with a few impressions that I believe are reasonably accurate. I found São Paulo to be like a big, unpolished gemstone: it's obviously valuable, but with all that grit it's hard to estimate exactly how much it's worth. More specifically, I loved the cafe culture and meeting so many friendly, educated and outgoing Paulistanos. And boy, was I a fan of the coffee, fresh juices and, of course, the beer. On the other hand, I wasn't so enamored with the aging buildings, nor was I happy about the level of crime that locals - including my friend Seth - have to face every day. Last but not least, São Paulo really isn't the best place for runners, not unless you enjoy taking your life into your hands. But would I go back to São Paulo? What's a little dirt between friends?