If I had to date this mix, I'd say that it is from the late 90s, after I moved in with Matt in Hoboken. The inclusion of Sinatra's Summer Wind is the tip off - it is a song that stamps that moment of time, us living in his hometown. Every time we'd eat at Johnny Rockets, it would be one of the two songs we'd play on the jukebox with our free nickels. (The other being Springsteen's Glory Days.)
There is quite a bit of this mix that ended up as part of our wedding - Crazy Love was our first dance, and we asked the DJ to play Brandy as an inside joke with one of our groomsmen. Summer Wind was also our bridal party dance, such that it was (our bridal party not being of equal pairings, so really just the people in our wedding dancing with partners).
All wedding talk aside, this isn't a love song mix. It was meant to be a set of songs to soothe the soul. One of the most endearing things Matt has ever admitted is that he sings both Ooh Child and Lovely Day to himself when he's stressed. The rest of the mix just flows around that.
Crazy Love - Van Morrison (1970)
Summer Wind - Frank Sinatra (1966)
Shelter from the Storm - Bob Dylan (1975)
Seasons of Love - Rent Cast & Stevie Wonder (1996)
Ooh Child - Five Stairsteps (1970)
Lovely Day - Bill Withers (1977)
Brandy - Looking Glass (1972)
Somebody to Love - Queen (1976)
Rocket Man - Elton John (1972)
Midnight Train to Georgia - Gladys Knight & the Pips (1973)
Lost it in the Sun - The Gathering Field (1994)
Fun Facts -
1) I make a mean Pip. Every time I sing along with one of Knight's songs, I'm always a Pip. Woo woo!
2) I'm fairly certain that Lost it in the Sun was on this mix for this lyric: I took a plane from Worcester back to Pittsburgh, admitting to myself even then that as much as I loved Hoboken, Pittsburgh would always be my home.
3) The name of this mix tape comes from Say Anything. Because John Cusack & Jeremy Piven have always made me happy.