I kind of feel like it reflects badly on him and not at all for her.
TS has had a series of fairly short relationships. She jumps from one to another and she now has had one unfortunate overlap. She instagrams every aspect of her life. But she's 25 - all pretty normal behaviour for someone her age. She is also an international megastar who is hyper aware of her image and makes no secret of that fact. She has never as far as I am aware complained about being papped, and indeed uses it to control her personal narrative. When I see these pics I see Swifty doing what Swifty does. She's not pretending to be anything other than what she's always been. She offers us a manufactured insight into her private life and we accept it for what it is.
But TH as we all know bangs on constantly about wanting to be authentic in his interactions with the press/the fans/the world. He says what you see is what you get. He also says he doesn't want to discuss his personal life. However what we actually get is him participating in an obviously staged photoshoot pretending to be taken when they were unaware, and pimping out a relationship that on their publicists' timeline is less than 2 weeks old. It feels like he has been feeding us a line. It also feels like he is an older guy with a slightly dodgy tendency to home in on younger women who already have boyfriends.