Background: I (M) was single and around 24 at the time. My boss (F) was around 35, married and with a kid.
So, my counterpart at work was scheduled to go with my boss to a conference at a nice large resort. Unfortunately, for him some family stuff came up last minute and I was selected to go in his place since everything had been booked and purchased by the company.
My boss and I meet up at the airport and have different seats on the plane. We check-in at the resort and our rooms are on the same floor but on completely different sides of the resort building. Our first few days at the conference at pretty uneventful. We meet in between conference sessions and trade notes, after the conference for the day we usually have dinner together and then go do our separate things.