 Pari gbolohun ti o tẹle: Ni Kínní 1995, Yearwood tu awo orin kẹrin rẹ silẹ, Thinkin About You, eyi ti o ṣe itọsọna diẹ sii si awọn aṣa agbalagba ti ode oni. Àdàkọ náà gba àyẹwò rere láti ọwọ Rolling Stone tí ó fi Thinkin About You wé ọpọ àwọn àdàkọ Linda Ronstadt ní àwọn ọdún 1970. Àdàkọ orin Melissa Etheridges You Can Sleep While I Drive àti Tammy Wynettes Til I Get It Right wà nínú àdàkọ náà. Thinkin About Yous first two singles reached number 1 on the Billboard country chart: XXXs and OOOs An American Girl  and the title track. Thinkin About Yous first two singles reached number 1 on the Billboard country chart: XXXs and OOOs An American Girl  and the title track. Ọkan-ọkan rẹ kẹta, I Wanna Go Too Far de oke mẹwa lẹhin itusilẹ rẹ ni opin ọdun 1995. Bíi ti àwọn orin tó ṣáájú rẹ, Thinkin About You ta mílíọnù kan àdàkọ ní Orílẹ-èdè Amẹríkà tí RIAA sì fún ní àmì ẹyẹ platinum. Níbi tí : 1995 Grammy Awards, orin olorin meji ti Yearwood ati Aaron Neville ti a pe ni I Fall to Pieces awọn awo orin 1961 ti Patsy Cline ti gba ninu ẹka ti Ijọpọ Orilẹ-ede ti o dara julọ pẹlu Awọn Orin. Èrè náà di èrè àkọkọ tí Yearwood gbà láti Grammy. 