Looking for tips on capturing someone who is self-conscious

Hi all. I have been quite amateur at photography for a while. I've had a Canon EOS 77D that I've used with an EFS 10-18MM lens for recording short films for a while. I'm about to go on a trip soon and want to take some pictures of my beautiful friends while we are abroad. At the recommendation of a friend who is into photography, I grabbed a new lens, an EFS 15-85mm. I'm extremely impressed by the pictures I've been taking with it.

My question is this: someone I will be traveling with is really self conscious and typically doesn't like any of the pictures they're in. At all. They usually say they look "heavy" or "ugly". Which is such a shame because they're gorgeous. I want to take pictures of them while I'm out in a way that gives me the best chance of capturing them in a way they like. For context, they have fair white skin, dark hair (nearly black), and typically wear very plain clothing (black, brown, tan, white). We will primarily be outside, on the beach and in a desert.

Thanks so much in advance for any help here