Start time: 1 p.m.
1. Meet at Raffles City.
2. Lunch at Yet Con along Purvis Street: old-school chicken rice, with some sambal kangkong for extra kick.
3. Hop on a bus to Chinatown, where Maxwell Hawker Centre serves as Exhibit A for introducing the concept of hawker centres. Interlude: sugar cane juice and deep-fried sweet potato dumplings. Marvel that at least 15 people are waiting in a very slow line for Tian Tian Chicken Rice.
4. Wander over to BooksActually, so I can pick up Concave Scream's new album. Peek into cool old clan association buildings on Ann Siang Road along the way.
5. Mosey further down Smith Street and the madly touristed-with-souvenir-stalls Trengganu Street. Puzzle over the juxtaposition of souvenir stalls with sex shops with eating places with traditional Chinese medical halls and a doctor's clinic that looks like it's permanently stuck in the 1950s. Admire Majestic Theatre from the pedestrian bridge linking Pagoda Street to People's Park Complex.
6. Hop on a bus to Tiong Bahru. Refresh spirits with ice cream ice kachang (that's not a typo), a cold bowl of cheng tng and a cup of ice-blended cappucino --- all from the same stall at Tiong Bahru market.
7. Maunder around Tiong Bahru, admiring Art Deco architecture.
8. Hop into a taxi to Beach Road market, so that the friend can get a Singapore flag cloth patch to add to his round-the-world collection.
9. Hie over to the Arab Street area and mooch around the food festival going on at the Malay Heritage Centre. Snack of the hour: prawn vadai.
10. Shuffle across the street, just in time to see the men coming out (or is that going in?) for evening prayers at Sultan Mosque. Finger fabrics at the cloth shops along Arab Street, peer at the indie-ish cafes and boutiques along Haji Lane, and nod approvingly at graffiti on the walls wherever you see it.
11. Pop into Parkview Square, 'cause it's the only crazy Gotham-like building we have in Singapore.
12. Nip into the National Library, so that I can use the toilet. Meanwhile my friend finds some kind of nifty touchscreen newspaper-browsing device.
13. Hop onto a train to Buona Vista. We're early for dinner and there are no tables available at the coffeeshop anyway, so poke around in the adjacent NTUC Fairprice supermarket and cool off in the air-conditioning.
14. Settle down at the coffeeshop for dinner.
15. Dawdle for a couple of hours over Peranakan food and Western fare, as one ought to at Big D's.
16. Adjourn to Udders for dessert, since the friend has declared, "I have a separate ice cream stomach."
17. Drop the friend off near his backpacker place at Little India, after helpfully pointing out Mustafa as a landmark and all-night shopping option.
End time: 10:45 p.m.