I also think the first one is probably doing a little bit more 'entertaining'.
The second one - is the clue about his 'friends'?
#1 Just to wind people up on here, was it a male flight attendant?
#2 I'd suspected that as I'd not read of him having a girlfriend for about 10 years! However, according to Wikipedia, he's been in a relationship with a Mean Girl for a long time.