Milan

Light up a cigarillo at Giacomo, where you can snack on a freshly-cut charcuterie plate, or even sip some Prosecco.

Centrally located above it's popular namesake bar, Straf offers beautifully-lit rooms with evocative art decorating the walls. You can easily slip in and out unnoticed through the hustle-bustle. There's a small pool and a sauna to complete the experience.

It's getting dark, you enter into what amounts to be a small room. A Tribe Called Quest plays on vinyl at the perfect volume. It’s the kind of place where you feel at home. The owner is also a London-trained chef. The food is subtle and satisfying, but it’s the tone of the place that stays with you. Perfect for a first encounter. Make sure you reserve via email beforehand as it tends to be packed on weekends.

A few steps from Duomo Il Marchese offers great food, a well-stocked bar and kind staff. But it's the interior design that makes Il Marchese a must-stop. It's perfect if you’re with someone from work, this is where the dynamic can quietly shift. They'll know you mean business.

Start your day with a true specialty coffee at Orsonero. They serve a lovely cortado, which is rare in espresso-obsessed Italy. Seating is limited, so might as well make a friend and join their table.

Begin on the first floor: warm lighting, Japanese bites, low conversation. On weekends, the Klipsch sound system hums to life, and music takes center stage. If you’re with someone worth leaning into, ask for Madame Cheng’s upstairs. A discreet room above it all, with velvet sofas, hushed cocktails, and the occasional unexpected connection.

A Milano-classic. Order blindly from the menu, there's something for everyone, and everything is great. If it's truffle season, make sure to ask for dishes that are served with fresh truffles.