Idiom: A night on the town
Meaning: an evening when people go various places and enjoy different types of entertainment such as dancing in a nightclub, eating in a restaurant, or drinking in a bar.
Context #1 – Kiki just graduated from UCLA and her friend wants to take her out to celebrate
Gerry: Congratulations, Kiki! You made it! How does it feel to be a college graduate?
Kiki: It feels great! All those years of studying are now worth it.
Gerry: Well, I want to take you out to celebrate. Why don’t we go out for a night on the town this weekend?
Kiki: Oh, that sounds like fun! Where should we go?
Gerry: It’s up to you. You should choose since we are celebrating your graduation.
Kiki: Well, I love dancing. Do you think we could go to that new nightclub that just opened up in West Hollywood?
Context #2 – Jackie has friends coming in from out of town
Jackie: A couple of my friends are coming to visit from Florida next month. This is their first time to LA and I really want to show them a good time.
Tommy: Well, LA is known for its nightlife. Why don’t you take them out for a night on the town?
Jackie: That’s a good idea! In fact, we could go to a really nice restaurant and see if we can spot any celebrities! That would be fun.
Tommy: Yes, but you had better make reservations right away for that kind of restaurant.
Jackie: I’ll do it now. This will be a night they will never forget!
Meaning: “In context 1, they are going out dancing to celebrate Kiki’s graduation from UCLA. In context 2, Jackie is planning to take her friends out to a really nice restaurant in LA and she is hoping to see some celebrities there. Both are typical examples for the idiom a night on the town.