The Docklands after ten, with someone who knows where the lights stay on

Nothing here is fixed. Tell Philippa the mood, loud or low-key, and your companion arrives with a plan she is happy to abandon. A typical three hours on the estate might look like this.

• 20:30. A drink at The Grapes in Limehouse, the river black and slow outside.
• 21:30. Live music at Boisdale in Cabot Place, a table with the stage in view.
• 23:00. A last drink high above South Quay, the towers lit on every side.
• 23:30. Back to the hotel, or wherever the night suggests next.

Stratford is a few stops up the Jubilee line and has a different energy: crowds spilling out of the London Stadium, bars and restaurants around Westfield, and hotels by the Olympic Park with terraces open on summer evenings. Book her from your hotel on Canary Wharf, ride up together and come back when you are done. The DLR runs there too, so the journey back is simple even after the crowds have gone home.

Not every night out needs volume. Cross the river to Greenwich for a pub beside the naval college, a late drink in the market streets and the river bus or a taxi back to the towers. It is quieter than the estate and far prettier after dark, with the Cutty Sark lit on the waterfront and the domes of the college floodlit behind it. Two hours at £500 covers it comfortably, three if you would like dinner first.

Thursday is the estate's big night. The bars around Cabot Square and Crossrail Place fill with teams marking the end of the week a day early, the music at Cabot Place runs later, and the high bars on Marsh Wall need a table held. If you want a Thursday with a particular companion, message by the middle of the afternoon; later, the desk will still find someone, from a shorter list.

The estate's bars are relaxed about clothes on a Tuesday and far less relaxed on a Friday. Tell the desk where you plan to finish and she dresses for the smartest room on the list, not the most casual. For you, a jacket solves most problems and trainers cause most of them. If a door is going to be difficult, she usually knows before you reach it, and she will have a second room in mind a short walk away.

Molly starts from ten, loves house music and chrome-era cars, and is happy long after the last DLR. Angelika will always choose the band over a quiet bar and wants a table with the stage in view. Tina, 158 cm with espresso brown hair, who carries more records than seems sensible, can often say yes on the night. Stacy, tall and dry-witted, likes a late comedy bill and a camera walk along the river. Three of the four are on the early twenties page.

The DLR winds down after midnight, the Jubilee line a little later, and the Night Tube runs on Fridays and Saturdays. Most guests take a taxi for the last stretch. Her own journey home is included within Zones 1 and 2, so the only fares you pay are yours, and she never waits at a cold platform at one in the morning on your account. If you would like her to stay on, message the desk before the three hours run out; the booking page explains how an extension works.