"Wishful Drinking" is the first duet between the artists. Andress stated in a press release: "I've never done anything like 'Wishful Drinking' before, I've always wanted to work with Sam and have been such a fan of his for a long time. I admire how he stays so true to himself and am so happy to have him join me for my first collaboration. The song was co-written by my friend JP Saxe, and it became this amazing sad bop, which we all know I love". Hunt said: "I heard Ingrid's music a while back and knew right away she was a very talented singer and songwriter, I met her not long ago at a
Nashville Sports League kickball game and I really enjoyed getting to know her a little bit. When the opportunity came along to be a part of this song with her, I was all in". Lauren Jo Black of
Country Now described the song as "a story of a couple who is trying to move past a breakup and find themselves thinking of one another when they drink".
Rolling Stones Jon Freeman stated that "Wishful Drinking" has a "sleek,
R&B-flavored production" containing "hints of
Dobro and acoustic guitar". ==Critical reception==