Picking songs that other people are going to listen to is VERY STRESSFUL. Like, I think I have good taste in music, but literally no one doesn't think that about themselves. If they thought what they liked didn't show good taste, it would thoroughly undermine the entire concept of good taste and that would be the nucleus from which the end of the world sprouted. (No? Are you sure? Like, double check quantum physics and get back to me. I don't fully understand quantum physics but I went to an engineering school and am pretty sure someone there told me once you could use them to explain any damn thing you wanted, and this is the quantum-music-taste hill I'm going to die on.)
When I was in Portland with my little brother last weekend we had a whole app based youtube queue set up on his chromecast (<- today in sentences Emma from ten years ago would think were gibberish). We were all adding, and it was skewing rap heavy because that's mostly what he and his friends listen to. I could have backed off and let it happen, but I wanted to contribute and also not to listen to rap for four hours.
(I don't dislike rap but I have a hard time staying engaged when there's not a through melody. Like, I'm a huge Childish Gambino fan, but my brother hates him... I guess he's intro rap? Because ... of the melody? I know it's shocking, but this is NOT something we covered in engineering school. All your preconceptions blown, right? Right.)
My approach was either great song or great video. I went retro a couple of times (Leave the Biker), full on pandering at least twice (see Lana del Ray and the Jenny Lewis video with Anne Hathaway and Kristen Stewart (a combo that surprisingly fills the needs of most people who like girls? Can I get an amen?)), and I'm not embarrassed to admit I appealed to my brother with people we've seen together.
That is way too much thought.
Literally, what is the worst thing that could have happened? That my brother's friends didn't think I was cool? I'm his older sister - they were pretty decided on the coolness of me long before now. (Probably I won some of them over when I looked super fly in a suit as his best man a few years ago.)
These are phases I go through. It's like I'm scared, sometimes, to take up too much room in the world. To make someone do literally anything that's not exactly what they had planned.
Probably I need to switch over to some Blondie. Some Tegan and Sarah. Some Tove Lo. Sometimes it's ok to play your own song.