 Who should pay the restaurant bill? According to etiquette experts. On a first date, did you propose the date you pay? At a coffee shop, you can always arrive early in order first, you pay for your own. If you're meeting to ask for a favor though, go ahead and cover it. With friends, if it's a small group, put it on your card, then we'll request everyone immediately. If you're in a big group, you have a couple options here. You can do the mimic method where you all order the same amount and split the bill evenly or take your split and square it up with your server. Now let's talk about the beast that is birthday dinners. The only thing here to remember is the guest of honor does not pay. So what if you're hosting the event? It's on you to decide if you're covering everything, but you must communicate otherwise so people are prepared. How about work dinners? If you're the boss, it's on you. If the boss is there, go ahead and put your wallet away.