I'm posting this here, because I honestly don't know the answer, so don't be too hard on me!
This is a good friend I've known for nearly 20 years. We take DC to football together regularly (my DH and his DW prefer not to go).
There is a game coming up at a famous seaside town c. 2.5 hours drive from home. It will be on a mid-week eve in the summer holidays and we've discussed the possibility of making it a big summer treat for the DC, by travelling down in he morning for a day on the beach, pub dinner and the game. The game ends c. 10pm, which is already a late night for the DC (ages 8, 10 & 11) but it is the school hols.
If I was going on my own, with a female friend or with DH, I think I'd go for the option of the overnight stay, rather than getting DCs home around 1am.
The is a lovely man who I would trust completely with mine and my DCs safety. I expect the boys will want to room together so sleeping arrangements would be 2 rooms, one with the 3 boys and probably me (younger DCs are mine) and my friend in the other room on his own - unless I can persuade him to swap!
We'll be well chaperoned and I can't really see anything wrong with it, it's just a feeling that it's not quite right. Friend's DW is apparently fine with it - glad she's not expected to go! DH says he's OK, but he did hesitate a bit.