You are not booking conversation
During the gig, the play or the second half, nobody talks. The company is everything around it: the queue, the drink beforehand, the interval, the ten minutes of walking out through a crowd, and the journey home.
That makes it one of the easier first bookings, because there is no pressure to keep an evening's conversation going. The event does the work; he is there for the parts of the night that are otherwise quiet.
The spare ticket
Tickets and entry are the client's, and they are confirmed with you before the booking rather than raised on the night — so if the ticket is already in your pocket, say so when you book and the estimate reflects it.
If you are buying one for him, buy the seat next to yours rather than the cheap one two rows back, and check whether it is standing or seated before you do.

Tell him what he is walking into
- Who is playing, and whether he needs to have any opinion about them
- Standing or seated, indoors or out — a stadium in November is not a concert hall
- The dress code, if there is one, and how much walking is involved
- How late it finishes, and whether you want to stay for the encore or beat the crowd
- Whether you want to talk about it afterwards or go straight home
Getting out and getting home
This is the part worth planning, and the part most people leave to chance. Twenty thousand people leave a venue at the same moment, phone signal disappears, and the last train is a real deadline.
Agree where you are meeting — a public place near the venue rather than the venue's own crush — where you will regroup if you are separated inside, when the booking ends, and how each of you is getting home. Tell a friend the plan. None of it is unusual advice for a big night out; it is just easier to follow when it was agreed before the doors opened.
Frequently asked questions
Do I have to buy his ticket?
Tickets and entry are usually the client's, and they are confirmed with you before the booking, so nothing appears on the night. If you already hold both tickets, say so and the estimate reflects it.
Does he need to like the band or the team?
No. He is company for the queue, the interval and the way home rather than a fellow fan. Tell us if you would rather have someone who does know the sport, and we will suggest someone it suits.
Can we just meet at the venue?
Yes, and a public spot near it works better than the entrance itself. First meetings in public places are recommended anyway, and a busy venue is about as public as it gets.
Is it awkward if we have never met and can't talk?
Less than you would think. A shared thing to watch takes the pressure off a first booking, and the talking happens in the gaps rather than for three hours straight.
