If you're trying to test out the waters to see if your crush is also into you, it's almost never a good idea to lead the conversation by sending nudes right away. Unsolicited sexual texts are jarring and uncomfortable for most people, but especially upsetting if they're photos of your teenage daughter's friend? Yikes! It's good to be confident and bold and make the first move, but that has the potential to be a huge swing and a miss.
So, when a concerned dad in this exact situation consulted Reddit's "Am I the As*hole?" for advice on whether or not he did the right thing, people were there for him.
I'm a 37 year old man. My daughter and her friend (I'll call her Brooke) are both 19. They met in college - they've been friends for almost a year.
Brooke's come over to our house too many times to count and she's always made me uncomfortable. Though she'd never explicitly flirted with me up until a couple days ago, I could always tell she liked me. But because there was no proof and she never made a move, I just tried to ignore it and keep my distance. She seemed like a good kid; never in a million years did I think she'd take it any further than laughing a little harder than necessary at my jokes.