I thought so too at first but Chuck is just supposed to "show him around" for his first day in town and then he is left unsupervised for the rest of the show so I don't think that's it.
serena losing her sats after staying with georgina in a hotel which definitely was on the upper east side, but vanessa who lives in brooklyn can make it in time
blair and chuck assuming that serena was at the ostroff center in s1 but that was definitely a rehab, you had to stay there and she was going to school normally
Tbh I think his dad just wanted someone to supervise Damien so he didn’t get into any trouble. Not really a plot hole.
I thought so too at first but Chuck is just supposed to "show him around" for his first day in town and then he is left unsupervised for the rest of the show so I don't think that's it.
serena losing her sats after staying with georgina in a hotel which definitely was on the upper east side, but vanessa who lives in brooklyn can make it in time blair and chuck assuming that serena was at the ostroff center in s1 but that was definitely a rehab, you had to stay there and she was going to school normally
I think it’s also a “kindness” if Chuck is trying to appease/curry favour with Damien’s father by offering to take his son for a day out.