Rip-your-heart-out playlist for when your child is leaving home

A shocking number of you have requested the playlist that Victor made to listen to after we dropped Hailey off at college because I guess you all really like to cry as well. No judgement.

And Hailey is loving college, which makes it so much easier, although I’m still a bit weepy and untethered. They called this morning to tell me that they’re getting involved in lots of activities and had spent the morning in a mental health workshop focused on group mind control. And I was like “Jesus Christ, those crazy-ass republicans were right for once…call your father, you’re in a cult” but turns out Hailey was just distracted by lunch when they were telling me about it, and instead of “Focused on Group Mind Control” it was actually a “Mindfulness Group Focused on Breath Control.” Phew.

And here’s your list of songs to listen to (or block) when your kid leaves home for the first time:

Feel free to add your own heart-breakers in the comments. I’ll just be listening to “Never Grow Up” on repeat while I sob into the cats. It’s fine. Everything’s fine.

142 thoughts on “Rip-your-heart-out playlist for when your child is leaving home

Read comments below or add one.

  1. I have my first check for $15,000. I have a lot of energy so I always have something first. p88 Now I’m going to work a lot harder and barely finish next week’s episode. w I strongly encourage everyone to sign up. .

    (This is the worst song suggestion ever. Wtf, Gloria. ~ Jenny)

  2. “Hold On,” by Tom Waits, “Keep Me in Your Heart” by Warren Zevon, “The Loneliest Guy,” by David Bowie, “You’ll Be Okay” by Great Big World, and of course “Long, Long Time” by Linda Ronstat.

  3. Wonderful playlist! Thank you.
    Everything is going to turn out fine. They’ll be home for a visit before you know it. And your pets will appreciate the extra love you have to give them, except they may be a bit depressed that one of the pack is not there, so be understanding of pets moodiness and a little bad behavior until they get past it.
    Hugs to all the parents of students going off to a new school.

  4. Things that made me laugh out loud today:
    1. Call your father…you’re in a cult

    Sadly, that’s it. But it was a good one!

  5. Since she went to junior prom, my song for my daughter has been Brandon Rhyder’s “Freeze Frame Time.” I was going to dance to it with her at her wedding but she knew I’d be a hot mess so she nixed the idea of a mother/daughter dance. To this day, twenty years and three grandkids later, I still choke up when I hear it. “We’re a little bit older now, together we’ve seen some change, but I love you more now than I did on that very first day.” They say good parents give their kids two things: roots and wings. That second one is so much harder, but it gets better, I promise!

  6. I’m saving this for next year, when my kid leaves. Where the &#*@ did the time go?

  7. Oh. This is an excellent playlist. And I don’t even have anyone moving out (although I kinda wish I did!).

  8. Just some reminders, Jenny…1) if you feed them, they keep coming back, 2) “Home” is always what it was and where YOU are, 3) Your baby will always be your baby, 4) Adult children are amazing!, 5) “Ugly crying” about your Baby moving away is actually very beautiful, 6) Your fridge is Hailey’s fridge for all time.

  9. Landslide by fleet wood Mac
    Hey there delihia -???

    Do not watch Toy Story 3!!!!!

  10. She’s Leaving Home by The Beatles (at least they aren’t “meeting a man in the motor trade”!)

  11. She’s Leaving Home by The Beatles (at least they aren’t “meeting a man in the motor trade”!)

  12. “These Are Days” by 10,000 Maniacs. “You know it’s true, that you are blessed and lucky….” *sob*

  13. I have my first check for $15,000. I have a lot of energy so I always have something first. h94 Now I’m going to work a lot harder and barely finish next week’s episode. w I strongly encourage everyone to sign up. .

  14. I’m bookmarking this particular blog, I have 2 that have graduated & are planning to spread their wings in the next few months. My youngest still has 2 more years of HS but today we just laid out his class schedule until he graduates & talked about the Tech Center he will be doing alongside HS classes. It’s so hard to think they are that old. Hugs to you, all the hugs, if you want them.

  15. So Far Away – Staind
    Anywhere Away From Here- Rag & Bone Man + Pink
    Leaving on a Jet Plane – Chantel Kreviazuk
    Where You Lead I Will Follow – Carol King

  16. There Goes my Life – Kenny Chesney

    We’re dropping Jess off TODAY. And now I’m crying. I know we’ll all be ok. Glad Hailey is already having fun!

  17. Ok, who’s putting this on Spotify for us? College drop-off is next week for my son, and I need to be ready.

  18. I cried for three days when my oldest left the first time.
    Trust me, it gets easier.

  19. Never Grow Up by Taylor Swift has leveled me since I first heard it, and my daughter used to laugh at me about it. Now she cries with me!!

  20. Kenny Chesney There goes my life
    Kenny Chesney Don’t blink
    Trace Adkins You’re gonna miss this
    Ah hell might as well add Kenny Chesney The Good Stuff since we’re already crying.

  21. The one that sends me over is that country song….There goes my Life (not sure the name). I started crying trying to tell my husband about your playlist and how that one should be on it.

  22. Aww, it will get easier, Jenny. Wait until she calls you in the middle of the night and scares you half to death because she wants to tell you something awesome that happened. For my daughter (born and raised in Southern California) it was when it snowed for the first time when she was going to NYU. Pictures of snow angels followed. May your call and snow angel pics come soon! And I’m so happy Hailey is having fun! ❤️

  23. I have my first check for $15,000. I have a lot of energy, so I always have something first. v2 Now I will work much harder and will hardly finish next week’s episode. and I strongly encourage everyone to sign up. .
    points, here…….…

  24. I’m really hoping someone makes this a Spotify playlist so I don’t have to.

  25. Dreaming with a Broken Heart, John Mayer; When Someone Stops Loving You, Little Big Town both bring on the tears for me

  26. “Shanghai Breezes” lyrics
    John Denver Lyrics
    Play “Shanghai Breezes”
    on Amazon Music Unlimited (ad)
    “Shanghai Breezes”

    It’s funny how you sound as if you’re right next door when you’re really half a world away. ***[million=20-ish–same::same]***
    I just can’t seem to find the words I’m looking for to say the things that I want to say.
    I can’t remember when I felt so close to you, it’s almost more than I can bear.
    And though I seem a half a million miles from you, you are in my heart and living there.
    And the moon and the stars are the same ones you see, it’s the same old sun up in the sky.

  27. “When She Loved Me” by Sarah McLachlan…gets me every. single. time. 🙁

  28. Great playlist & great additional suggestions! It’s a tough one, but it does get better. Took me about 6 months when my last kid went to college & I really had an empty nest. Practice those deep breaths while you cry on the cats. Hugs!!

  29. These are Days – 10,000 Maniacs
    Orphan Girl – Gillian Welch
    It’ll Be Easier in the Morning – Hothouse Flowers
    If I Should Fall Behind – Bruce Springsteen

  30. Why would you let Victor torture you like this? Are you okay? Should I call someone? Blink twice if yes!

  31. I have an upcoming high school senior and I have a playlist I’ve been curating for his graduation. Songs he loved as a kid, songs I used to sing to him, songs we sang to together these past years. I’m going to give it to him as a graduation present and a part of me is going to fall into a million pieces.

    I hope he’ll listen to it when he needs to know how much I love him.

  32. “100 Years” by Five for Fighting. That song has an oddly suspicious way of showing up in my life at really bad times, but just occasionally out of the blue as well, which is how I ended up crying in an elevator once on the way to a job interview. FML.

  33. Taylor Swift will slay you one way or another, best of the best and heartbroken of the heartbrokenest. A wonderful mother-child “how did they grow up so fast?” song is Donovan Woods’ “What They Mean.” I experienced my first college drop-off one year ago and am not properly prepared for version 2.0 in a week or so.

  34. This, right here, is every reason not to let your kids skip ahead in school! My son is 22 and I just saw him off for the SIXTH YEAR on Monday. Aggghhh! It’s killing me. And he’s an opera major, so listening to anyone sing is its own special torture.

  35. Dropping my son off on Friday. Already melting. I’ve built this playlist including all the songs in the comments and expect there to be tears.

  36. Shit! I don’t need a playlist to make me cry when I drop my son off. I cried off and on even after I got home (10 hours of driving). I’m a mess just looking at the titles! sigh… But this is what we raised them to do – right? sigh…

  37. “Time After Time” (Cyndi Lauper) and “Forever Young” (Rod Stewart) came on the radio as we drove our son to college the first time. I was maintaining until those came on.

    It does get better. About the time you get used to not continually restocking some grocery item for them, it’ll be holiday break, and you’ll have to hightail it out to go get it!

  38. Memories – from Cats. Butterfly Kisses. No One is Alone – Into the Woods. Go Your Own Way – Fleetwood Mac. Homeward Bound – Simon and Garfunkel. Leaving on a Jet Plane – John Denver. Empty Chairs at Empty Tables – Les Miserables. So Long, Farewell – Sound of Music. Goodbye Old Girl – Damn Yankees. Ti Moune – Once on This Island. Seasons of Love – Rent. You’ll Be in My Heart – Tarzan. How Far I’ll Go – Moana. Sheesh – I’m everywhere with list. And crying. Hugs.

  39. I know she’s already on there but why not a double? Sarah McLachlan When She Loved Me.

  40. I have been an avid The Chicks fan since the Wide Open Spaces album. Ironically I didn’t hear this song until I was watching a Medium episode years ago! This song perfectly describes the love between a parent and child, Lullaby by The Chicks.

  41. Wild World by Cat Stevens. I’m glad they are hitting their stride there.

  42. Not really about kids, but 1000 Years by Christina Perry and 100 Years by Five For Fighting make me tear up. Oh, and You’ll Be In My Heart by Phil Collins, off the Tarzan soundtrack. I’m not crying, you’re crying.

  43. Man, my kids are now 24 and 27, but reading this list (well done Victor!) and the comments just wrenched my mama heart out anyway. They are ALWAYS our kids. I’ll throw in “Ain’t no mountain high enough” by Marvin Gaye and Tammi Terrell. Also Gloria, go spam some other blog.

  44. Never Grow Up by Kenny Chesney. My daughter sent me the song right before she moved across the country. I firmly believe she has no heart.

  45. Our first daughter went to LSU exactly one hour away from home and my husband tells everyone I cried like they were closing the coffin on my child when we left campus that day. My second daughter went to Rhodes 6 hours away and I was doing fine when we pulled away and within minutes of exiting the gate the Kenny Chesney song “There Goes My Life” came on and guess who cried like a baby?? Not me!!! It was HIM! LOL And 6 years later that is the song that was her Father Daughter dance at her wedding. He kept his shit together – barely – that night.

  46. “As they drive away, her dad yells ‘Check the oil'”
    That line KILLED me when I was at college. I was lonely and alone and it was the only indication I had that they cared a little. Jenny I know your heart hurts but you’ve done SO WELL loving your child and making sure they know it and that makes me so happy because that love spreads.

  47. I have my first check for $15,000. I have a lot of energy, so I always have something first. s17 Now I will work much harder and will hardly finish next week’s episode. and I strongly encourage everyone to sign up. .
    points, here…….…

  48. Send ‘Em On Down The Road – Garth Brooks

    My son goes back for his junior year in a week. Never gets easier and he’s less than an hour away.

  49. I’m in the process of making a playlist for the celebration of my mom’s life (quite a different feel, of course), but some of these could work. Best of luck getting through the days with your kiddo so far away, Jenny. I hope they come home more than I did. <3

  50. “Somewhere Out There” – Linda Ronstadt and James Ingram. It gets me every time.

  51. Landslide – Stevie Nicks, Sunrise, sunset – Fiddler, Circle Game – Joni Mitchell, that old Polaroid commercial ( Turn around and she’s two, turn around and she’s four, turn around and she’s a young girl going out of the door)!!

  52. Another of my favorite cry-inducing songs is “The Call” by Regina Spektor, a must-add to your playlist!

  53. To those who suggested “Slipping Through My Fingers” by ABBA… this is just cruel. Appropriate. And necessary. But cruel.

    Glad they’re doing ok! You know they will!

  54. Home to You by Sigrid – oh my goodness! My daughter has danced to this twice and I am a wreck afterwards!

  55. This is a go-to for me when I want to cry. Also Cold, Cold Ground by Tom Waits. They are both very dark.

  56. Not seeing the ethereal Sarah McLachlan on here! I don’t even have a kiddo I’m letting go of, but if you need to grieve something or someone she is the one.. her album “Mirrorball” especially and the song “I Will Remember You” will take you back in time to 2002 at high school graduation (or perhaps that’s just ancient me talking) and it will destroy you in the best way.

    Also anything by Sara Bareilles will unearth the corners of yourself you didn’t know existed. “Manhattan” from “Blessed Unrest” although about lost love, is a song I feel deep in my bones about loss in general.

    John Mayer’s “Room for Squares” was my entire college experience album-Hailey might like that one and relate to it in their own way, cause they are going through stuff too-lots of changes!

  57. This is the Time (to Remember) by Billy Joel

    The Dance – Garth Brooks

    And truly awful? Butterfly Kisses.

  58. That was a hard listen. I just lost my dad. However, since I recommended Butterfly Kisses had to listen. Now I am bawling like a baby.

    Also I couldn’t even listen to the Dumbo song. That one with the video, Niagara Fall.

  59. Trying not to cry–I’m sitting at the car dealership waiting for an oil change. My third (and youngest) starts college next week. It hasn’t gotten any easier; I’m still just as weepy as I was with the first and second. So proud of the young men they’ve become, but it’s so quiet without them home

  60. I have my first check for $15,000. I have a lot of energy, so I always have something first. s95 Now I will work much harder and will hardly finish next week’s episode. and I strongly encourage everyone to sign up. .
    points, here…….…

  61. Will this work for the reverse? My daughter stayed home for college, but now that she’s 21, I am moving away from her (a few states away)

  62. “Meet Me at the Moon” always hit me after my son went away to college.

  63. There’s a new one by Noah Kahan that I don’t see listed here:
    “You’re Gonna Go Far”
    Lines that kills me: “We’re not angry at you love, you’re the best thing that we’ve lost” “and we’ll all be here forever”

  64. I am crying just reading the list. I would dissolve into a puddle if the music actually entered my ears.

  65. Far From the Home I Love from Fiddler on the Roof
    Song by Chaim Topol and Michele Marsh

  66. Mine has finished college but I’ll use this playlist when she moves from Dallas to Seattle soon. I’m not looking forward to being thousands of miles from her instead of the 250 when she was at UH.

  67. Michelle, I’m so sorry about your dad! About a year after I lost my dad I was driving with a friend and Butterfly Kisses came on the radio. I started bawling and had to pull over until I could get control of myself. I’ve not listened to it since that time.

  68. I just moved my oldest into her dorm in New Jersey last week but didn’t ugly cry until on the plane back to Austin yesterday. I’m so excited for her new adventure but man was it against all of my mama instincts to get on that plane and leave her there! I’ll be listening to your playlist this week and feeling all of the emotions. 😭

  69. I love that you have a partner who understands the process of music with crying, processing and growing, even if he didn’t quite get the little fish big fish song.

  70. I remember hearing this when my brother went off to college (CIA). Who knew that 5 years later I’d be attending the college next door that I had never heard of (Marist).

    A cold, rainy, fall night and this song came on…

    Don’t Know What You Have… Until It’s Gone

    Life happens and if it’s well lived, you’ll never know where you’ll end up. Growth and change maybe be challenging, but remember, in time, it’s all good.

  71. When You Go by Jonathan Coulton – such a great song.

    Having kids go off to college is… weird. I mean, we spend years and years raising them to be functional independent adults, and then they go ahead and actually become functional independent adults and it just kind of breaks our hearts. Such is parenting…

  72. This is an amazing and also comically cruel playlist. I’m saving this post. My daughter’s apparently sadistic second-grade teacher made an end-of-year slideshow to “Never Grow Up” during class awards day, and I had to sit there sobbing for four minutes while somehow all the other parents kept their shit together. Good times. 🙂

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