I think that the best subject to start a conversation it is music. Every day I listen to music. How I'm learning japanese, I usually listen japanese music from the singers like Shiina Ringo (She is my favourite singer), Utada Hikaru (Her voice is so sweet) and the band Wagakki Band (Their music is mix of rock, pop and traditional japanese songs). And besides japanese music I like listen to brazilian music. I like MPB (Música Popular Brasileira), Rap (I like, but I usually listen only the music from the singer called Criolo, and He is a amazing singer. His musics lyrics is very hard to understand, even for braziians), Samba... Down below is a list of brazilian music that I like to listen to. And you guys, what kind of music do you like?
Elis Regina's songs: O bêbado e o Equilibrista; As Curvas da Estrada de Santos (This music is from the singer Roberto Carlos, but Elis' version is soooo good. You have to listen to this!!!); Como Nossos Pais; Alô, Alô, Marciano; Velha Roupa Colorida; Madalena; Fascinação; Maria Maria; etc. (The music that I like is more than that. So for more Elis Regina's songs search on Google. ;))
Novos Baianos' songs: Mistério do Planeta; A Menina Dança; Dê um Rolê; Tinindo Trincando; Brasil Pandeiro.
Tim Maia's songs: Ela partiu; Gostava tanto de você; Me dê motivos; Que beleza; Azul da cor do mar.
Caetano Veloso's songs: Desde que o samba é samba; A luz de Tieta; Nine Out of Ten; You don't know me; Você é linda; Menino do Rio (listen to the Baby do Brasil's version. Baby is from the group Novos Baianos).
I can't write all the musics that I like here. But listen to Tom Jobim's Wave and Samba de Avião, Gilberto Gil's Drão, A paz, Aquele Abraço and Toda menina Baiana.
Criolo's songs: Duas de Cinco; É o teste; Bogotá; Até me emocionei; Convoque seu buda; Subirusdoistiozin; Cartão de Visita; Espiral de Ilusão; Lion Man; Plano de Vôo; Chuva Ácida.
Mart'nália's songs: Pra quê chorar; Tava por aí; Pé do samba; Namora comigo; Don't worry, be happy!; Cabide; Entretanto.
Cartola's songs: Preciso me encontrar; O Sol Nascerá; O mundo é um moinho; A sorrir.
Maria Rita's songs: Coração em desalinho; Cara valente; Reza; Cadê Obá.
If you have another suggestion, put in the comments below. I tired to write :) I hope that you enjoy these songs. Bye guys.
I'd recommend you do start making playlists with music in different languages, it really encourages you to discover new music and it is easier to share with other people ;^)
I also like Tom Jobim. I like Brazilian Bossa Nova, French music, movie soundtracks and classical music
Broadway music is also entertaining for me