I was a huge “How I Met Your Mother” fan, which was my only real exposure to The Proclaimers’ 1987 recording, “I’m Gonna Be (500 Miles).” It pops up in a few episodes of the x-season series, and specifically in the episode “Arrivederci, Fiero.” The episode showcases road trips taken through the years in Marshall’s Fiero, a true beater of a car, with many problems including a broken tape deck—stuck on this song. The whole point is that the song becomes annoying and meaningless.

It was years after finishing the series that I randomly selected a playlist on my Apple Music, just to play in the background while I finished up some work. I found myself suddenly moved by a sweet Sleeping At Last ballad, and it wasn’t until they reached the chorus—“I would walk 500 miles, and I would walk 500 more… ”—that I realized it was that annoying song from “How I Met Your Mother.” Except, it turns out, it’s actually incredibly sweet.

Along with many other life lessons I learned from “How I Met Your Mother,” I came to understand the tendency to write something off, something that could be important and beautiful, simply because I’ve been exposed to it too much. Now it’s Valentine’s Day, and I’m not one to shirk big celebrations of love, Hallmark-mandated or otherwise, but it can be easy to gloss over the value of such a day when we’re always fed the same old cheese.

“I’m Gonna Be (500 Miles)” surprised me. I wondered what other songs were unexpectedly romantic, what I might have missed because, due to circumstances, I simply wasn’t paying attention. The good news is, I have a bunch of music buff friends who value the unexpected and unknown, and with their help, I conjured up a lovely little Valentine’s Day playlist, chock-full of sweetness that might surprise you.

Obviously, we’ll begin with the Sleeping At Last Cover, and it only gets better from there. A lot of these songs were unknown or misunderstood, overplayed on the radio or made trite by the sorts of people who claimed to love them; but if you focus on the lyrics, picturing that person you love (or in some cases, the love you lost)—and the way love changes over time—I think you’ll find some unexpected romance in them all.


—Sleeping At Last, “I’m Gonna Be (500 Miles)” from Covers, Vol. 1 (2014)
—Beach Boys, “God Only Knows” from Pet Sounds (1966)
—John Prine (feat. Iris DeMent), “In Spite of Ourselves” from In Spite of Ourselves (1999)
—Maroon 5, “She Will Be Loved” from Songs About Jane (2002)
—Dean Martin, “On The Street Where You Live” (1956)
—Coldplay, “Yellow” from Yellow (2000)
—Frank Ocean, “Ivy” from Blonde (2016)
—Lauv, “I Like Me Better” from I Met You When I Was 18 (The Playlist) (2018)
—Durand Jones & The Indications, “Is It Any Wonder?” from Durand Jones & The Indications (Deluxe Edition) (2016)
—Big Wild (feat. Rationale), “6’s to 9’s” from Superdream (2019)
—Carpenters, “Close To You” from Close To You (1970)
—Wolfsuka, “Baby You Know Me” from Poison to the Artists (2017)
—Lord Huron, “Harvest Moon” (originally by Neil Young), from Spotify Singles (2018)
—Phoebe Bridgers, “Killer” from Stranger in the Alps (2017)
—The Lumineers, “Cleopatra” from Cleopatra (2016)
—Hall & Oats, “You Make My Dreams” from Voices (1980)
—The 1975, “It’s Not Living (If It’s Not With You)” from A Brief Inquiry into Online Relationships (2018)
—Taylor Swift, “The Lakes” from Folklore (2020)
—The Secret Sisters, “He’s Fine” from You Don’t Own Me Anymore (2017)
—The Cranberries, “Linger” from Everybody Else Is Doing It, So Why Can’t We? (1993)