hi!! I meant to answer this after I finished the s3 chair outfits sorry 😭😭 so my simple answer is that I kinda hate it sksfjsk but I'll explain why so to start with I always found the fact that blair slept with jack during s2 so out of character. I get that she was meant to be upset that chuck left (and drunk??) but by that point blair's only slept with 2 people and I just can't imagine her finding comfort in sleeping with chuck's older uncle as a teenage girl. even in a grief infused state where maybe she thought it would be like sleeping with chuck I just don't think, based on her character, she would do it. ik she kisses random older guys like in 1x05 so even if they said she'd kissed jack and immediately regretted it I could believe that more, but the idea that she then had sex with him doesn't make sense to me. I understand that, at it's core, it was a decision for the drama, to create conflict between chuck and blair and also be able to come back later on in s3. but from a character perspective it's... icky. I do feel like the hotel incident in s3 allowed it to have slightly more depth, as it was clear chuck had never quite gotten over it as much as he said (him watching blair and jack in 3x15 suggests that he still feels there's something lingering between them which is why he's so distraught at the thought of them sleeping together again) and it became clear that it was part of the whole trust issue they both needed to work on. ultimately though I think it was a plot point that was mostly for shock and drama value bc that's the kind of show gg is (think the convenient shard of glass cutting blair's cheek or bart coming back) but there wasn't really any thought for what it meant for blair as a character to me bc it doesn't really fit with her personality or be something she would even entertain the possibility of, let alone do
