I've known one of my dad's closest friends for many years, almost as long as I've been alive! I have a lot of great memories hanging out with this man and his wife at their pool, going out to dinner, playing with their dog, the list goes on. Tragically, his wife passed away this last year and this loss has changed his life enormously. My dad and I have been trying to spend more time with him to keep him moving and out of the house. However, some of the things he says to me now are starting to make me uncomfortable. He bluntly discusses my physical appearance and what he finds attractive about me, quizzes me about boys and if I've kissed or done anything further yet, and most recently invited my father and I to his lake house and then privately texted me to say he hoped I packed my 'tiniest bikini'. I'm completely at a loss for how to handle this. I could tell my father, but I don't want to ruin their friendship, especially considering how recently he lost his wife. I could try to talk to the friend myself, but I don't know if he'd take me seriously or if he's even doing anything wrong and I'm just overreacting. How should I handle this situation while doing the least damage possible?
