• Alyssa Piperis

My Ultimate “Feels” Playlist: 50 Songs For Nostalgia, Heartbreak & Deep Love

I’ve been thinking a lot lately about the guys I’ve loved and the songs that have gotten me through breakups and low points in my life over the years— songs that bring me nostalgia, get me in touch with my emotions, and make me truly feel. There’s a big group of songs I always seem to come back to and a select two or three within that that can still make me cry while I’m driving in my car late-night, emotionally preparing for a scene as an actor, or lying in my bed reminiscing. So, I wanted to create one cumulative playlist of as many of those songs as I can think of (mixed with a good amount of newer favorites), both for me and for you. I know I, personally, have googled things like “songs for a broken heart” and “best breakup playlists” over the years (haven't we all?) to find lists from other people and bloggers that speak to exactly how I’m feeling in the midst of tough times and sleepless nights. And if I can provide that for others, that’s pretty dang cool. If you’ve come across this playlist and any of these songs hit you right in the feels, that’s exactly why it exists. I hope you enjoy this long list (and aren’t too overwhelmed by it) of my ultimate “feels” songs. They range in genre (alternative, country, indie, folk, soul, pop, “emo,” etc.), but the string that connects them all, I think, is their lyrical magic and poignance. They just make ya feel.

To make it easier to break everything down and find songs you connect with, I've included some key words and descriptions of what each song represents, as well as a sample to listen to. And if you ever just want to jump to the entire playlist, it's at the very bottom!

So, from me to you…

#1: Five for Fighting - The Riddle (You & I)

Filed Under:

Existentialism, Putting Things into Perspective, Love, Relationships, Meaning of Life, Father and Son, Parents and Children, Learning About Life, Simple Pleasures, Forever Young, Optimism, Pop/Rock

Will Hit You the Hardest When:

You’re feeling existential, want to put life into perspective, and remind yourself what really matters in the grand scheme of things.

#2: Ryan Beaver - How About You

Filed Under:

Longing, Loneliness, No Bullshit, Taking Risks, Fuck Small Talk, Country, Singer-Songwriter

Will Hit You the Hardest When:

You’re lonely, craving a romantic connection, and you’ve had enough of small talk. You just want cut the BS and get real with someone who wants to get real with you.

#3: One eskimO - Kandi

Filed Under:

Infidelity, Emotional Infidelity, Cheating, Hurting, Heartbreak, Delicate, Confusion, Misunderstanding, Indie Rock

Will Hit You the Hardest When:

You love someone more than you could ever say, but you don’t know if you can get over knowing they were physically and emotionally intimate with another person when you and your love were completely there for them.

*This is such a unique, powerful tune. I don’t remember how I discovered it, but it just hit me right in the gut. Whether you’ve been cheated on by someone you truly love or have been caught off guard by a person you love choosing someone else over you—or if you’ve been the one doing the cheating or choosing— this song shares a little of both sides of the story. It beautifully intertwines both people involved in a delicate situation, and I just love it.

#4: NEEDTOBREATHE - Drive All Night

Filed Under:

Wanderlust, Freedom, Seeking Adventure, Human Connection, Romantic Connection, Lost and Found, Finding Yourself, Change of Scenery, Closing a Chapter, Starting a New Chapter, Leaving Your Mark, Living Fully, Rock, Christian Rock

Will Hit You the Hardest When:

You’re ready as hell to close the current chapter and embark on the next one. You’re craving adventure, human connection, and a change of scenery. You don’t need to know where you’re going, but you need to go.

#5: Courtney Marie Andrews - Not the End

Filed Under:

Reminiscing, Trying to Save the Relationship, Indie, Folk, Country, Joni Mitchell-esque

Will Hit You the Hardest When:

You have fond memories and love in your heart and you don’t want it to be over.

#6: Mayday Parade - Stay

Filed Under: Deep Longing, Losing Someone, Depression, Making Mistakes, Reminiscing, Needing Space, Apologizing, Saying Sorry, Unhealthy Relationships, Can’t Sleep, Rock

Will Hit You the Hardest When:

You’re missing someone like crazy, you know you’ve both made mistakes, you’re feeling a little depressed, and you can’t sleep. All you want to do is see this other person without fighting and hold onto them as tightly as you possibly can.

#7: Elenowen - Cripple Me

Filed Under:

Personal Growth, Patience, Needing Time, Good Intentions, Pure Heart, Self-Love, Giving Love, Not Ready to Love, Folk Rock, Duo

Will Hit You the Hardest When:

You want so badly to be with someone and give them everything they need, but you’re not yet secure enough in yourself and where you need to be to do that. You can’t let yourself lose this person you love so deeply, so you’re waiting for—craving—the moment to hit you that shows you you’re finally who and where you need to be.

#8: Sam Hunt - Take Your Time

Filed Under:

Making a Move, Trying Not to Come on Too Strong, Being a Gentleman, Bar Flirtation, Innocent Conversation, Human Connection, Country, Rap, Pop

Will Hit You the Hardest When:

You feel drawn to someone and don’t know what they’re looking for, but you just want to talk to them and be around them. You have only the purest of intentions and want to connect.

#9: Corey Smith - Moving Pictures

Filed Under:

Old Love, Reminiscing, Love in the Age of Social Media, The One That Got Away, Real Talk AF

Will Hit You the Hardest When:

You keep coming back to that same one person. No matter how much time passes and who else you date and feel things for, your mind always wanders back to them. Every now and then you’ll scroll though old pictures and get lost in the memories. You miss it all. You wonder if the two of you will find your way back to each other. You hope the ship hasn’t sailed.

#10: Sara Bareilles - Gravity

Filed Under:

Finding the Courage to Let Go, Moving On, Emotional Abuse, Manipulative Relationships, Going in Circles, Pulling the Cord, Pop, Soul

Will Hit You the Hardest When:

You want more than anything to be able to just let go. You’re trying to walk away and move on, but the history and memories keep pulling you back in as though by a magnetic force. He or she always knows exactly what to say to make you second guess yourself, but you refuse to fall back in and keep going in circles.

#11: Brett Eldredge - Bring You Back

Filed Under:

Sudden Breakups, Fighting for the Relationship, Storytelling, Country

Will Hit You the Hardest When:

You’re still deeply in love with them and can’t let it be over without fighting for it. You keep replaying the beautiful memories of the past alongside the moment you saw them lose hope, and it breaks your heart.

#12: James Morrison - The Pieces Don’t Fit Anymore

Filed Under:

Heartbreak, Breakups, Surrender, When You Know It’s Over, Letting Go, Moving On, No Logical Explanation, Pop/Rock, Soul

Will Hit You the Hardest When:

You’ve given everything and, for no logical reason whatsoever, it isn’t enough. You’re having trouble eating and sleeping, wishing it were right, but knowing it just isn’t. And that breaks your damn heart. But you need to let go, and you need to let them let go.

#13: Matt Woods - In the Dark

Filed Under:

Dependency, Self-Awareness, Self-Love, Mutual Love

Will Hit You the Hardest When:

You’re with someone who’s always there to catch you when you fall and you’re endlessly appreciative, but you also understand that you need to learn how to catch yourself. You won’t always have someone else to fall into, and even if you do, you won’t be able to give them what they need if you’re not secure on your own without them.

#14: Jim Croce - Operator (That’s Not the Way it Feels)

Filed Under:

Heartbreak, Longing, Trying to Move On, Denial, Self-Awareness, Sadness, It is What it is, Folk, Pop Rock, 60s, 70s

Will Hit You the Hardest When:

You want to convince your ex-lover, as well as yourself, that you’re over them and the relationship. But you’re not. Your heart is heavy, and you think that, maybe, acting like you’re happy for them will make you happy for them. But it isn’t working.

#15: Guster - One Man Wrecking Machine

Filed Under:

Nostalgia, Adolescence, Looking Back, Searching for Meaning, Past and Present, Alternative Rock

Will Hit You the Hardest When:

You’re at a weird place in your adult life and just want to go back and relive those quintessential adolescent years and experiences.

#16: James Arthur - Say You Won’t Go

Filed Under:

Romantic AF, What We All Dream Of, Beautiful Love Story, X Factor UK

Will Hit You the Hardest When:

You’re completely in love and you know this is it for you. You’ve found the one, and there’s no doubt in your mind. There are countless magical and difficult memories, and you look backward with overflowing gratitude for the family you’ve created and forward with a full heart for the love you share. (Orrrr, you’re just dreaming of the day you can say this. :))

#17: Blue October - Home

Filed Under:

Living Fully, Happiness, Gratitude, Importance of Family, Simple Pleasures, Marriage, Alternative Rock

Will Hit You the Hardest When: You’re feeling an overwhelming sense of gratitude for the people and love in your life, and you want to hold onto that feeling for as long as possible.

#18: Austin Basham - Running

Filed Under:

Confusion, Making Tough Decisions, Heart Versus Mind, Traveling, Wanderlust, Soothing, Indie, Folk

Will Hit You the Hardest When:

You’re having a hard time figuring out what’s best for you. Staying or going. Holding on or letting go. Making a definitive decision or waiting things out.

#19: Lady Antebellum - American Honey

Filed Under:

Nostalgia, Wanderlust, Following Your Heart, Growing Up, Country Life, Small Town Living, Dreaming Big, Pure, Innocence, Adolescence, Freedom, Reminiscing, Summertime, Country

Will Hit You the Hardest When:

You’re filled with a wild mix of wanderlust and nostalgia, and you feel free and capable of anything.

#20: Chris Velan - Sweet Mary

Filed Under:

Reminiscing, Memories, First Love, First Time, First Sexual Experience, Growing Up, Looking Back, Summer Romance, Weed, Longing, Afrobeat, Folk Pop, Vintage Rocksteady

Will Hit You the Hardest When:

You can’t help but look back and wish you could experience all your firsts again— first love, first sexual experience, first heartbreak, first time really making love. It’s all in the past, long gone, but you find yourself longing for all those moments and feelings you know you’ll never get back.

#21: John Mayer - Comfortable

Filed Under:

Not Over Your Ex, Comparing Everyone To Your Ex, Unhappily Single, Old School John Mayer

Will Hit You the Hardest When:

You’re trying to get over someone by dating another someone who’s perfect on paper, but you can’t help comparing this new person to your ex. Your ex was beautifully flawed and goofy and into potty humor, and you had come to know each other’s quirks and insecurities and facial expressions. You’re not ready to give someone else a fair chance yet. You’re still trying to figure out if it’s your ex you should be with or if you just need time to get over them before giving someone else a real shot. (Okay, maybe I got a little too into this one…)

#22: Lord Huron - The Night We Met

Filed Under:

Losing Someone, Longing, Walking Down Memory Lane, Aimless, Searching, Unsureness, Nostalgia, Indie, Folk

Will Hit You the Hardest When:

You realize the chapter has closed and it’s really over. This person isn’t yours anymore, and all of a sudden they can’t be to you what they were just a day or week or month ago. You can’t hold them or kiss them or text them all your silly and deep thoughts like you could before. And it fucking sucks. You just want to go back in time so you can relive all the good moments…or so you can stop yourself from falling for them.

#23: Eli Young Band - Drunk Last Night

Filed Under:

Drunk Dial, Missing Someone, Regret, Heartbreak, Breaking Down, Getting it Off Your Chest, Country

Will Hit You the Hardest When:

You’ve been drinking and every little thing reminds you of how much you wish you still had them, whether the relationship was right or wrong.

#24: Ben Rector - Sailboat

Filed Under:

Feeling Lost, Aimless, Finding Yourself, Finding Happiness, Needing Comfort, Not Giving Up, Believing in Yourself, Pop Rock

Will Hit You the Hardest When:

You’re feeling alone and lost but you’re somehow at peace with that. You both love and hate how you’re feeling, but you understand it’s necessary for you to move forward and find your footing. You’re aching for something, or someone, to pull you in and make you feel safe, but maybe you have to pull yourself in.

#25: Matt Nathanson - Come On Get Higher

Filed Under:

Missing Someone, Craving Physical Intimacy, Sex, Desire, Folk, Rock

Will Hit You the Hardest When:

You know you shouldn’t be with someone, but the only thing you want right now is their body wrapped up in yours. You don’t care if it’s a mistake; you just want to make love to them and forget all the reasons you’re not together anymore.

#26: Brantley Gilbert - You Don’t Know Her Like I Do

Filed Under:

Breakups, Heartbreak, Losing Your Best Friend, Memories, Reminiscing, Unwanted Advice, Country

Will Hit You the Hardest When:

You’ve lost your lover and best friend, and it’s unbearable listening to people try and console you. You don’t want to hear that you’re better off without the person you love and care about the most. You know that the only person who can make you feel better is your ex, and the fact that they’re not a part of your life anymore is killing you inside.

#27: City and Colour - The Girl

Filed Under:

Deep Love and Appreciate for Your Partner, Gratitude, Sacrifice, True Partnership

Will Hit You the Hardest When:

You’re endlessly appreciative of your partner and all the sacrifices they have made for you to pursue your dreams, and you need them to know how much you love them and don’t take it for granted. You know everything will be worth the sacrifices, and it’s crucial they believe in that as much as you do.

#28: Ben Folds - Brick

Filed Under:

A Beautiful Disaster, Excellent Storytelling, Heartbreak, Emptiness, Exhausting, Abortion, Alternative Rock

Will Hit You the Hardest When:

You’re in deep…but not the way you want to be. You’ve gotten tangled up in something, or someone, that’s draining your energy, and you feel tired and helpless. It’s a tragically beautiful mess.

#29: O-Town - All or Nothing

Filed Under:

All In, Giving Your All, Giving Without Receiving, Nearing the End, Impending Breakup, Boy Bands, Early 2000s, Pop

Will Hit You the Hardest When:

You’ve been all in, putting in all your effort, and you refuse to settle for less than the same in return. You’re offering them one last chance to make things right, but deep down you know it’s over, a lost cause. (This is my throwback 90s boy band tune I always come back to!)

#30: Zac Brown Band - Colder Weather

Filed Under:

Bad Timing, Not on the Same Page, Creative Lifestyle, Following Your Dreams, Country

Will Hit You the Hardest When:

You’re trying to make it work with someone, but the timing and circumstances prove to be wrong, over and over again. You’re two different people with different lifestyles, and you realize this just isn’t that forever thing. You need to keep chasing your dreams, and they’re staying put.

#31: John Mayer - No Such Thing

Filed Under:

Growing Up, Following Your Dreams, Taking the Road Less Traveled, Going Against the Grain, Peer Pressure, Creative Lifestyle, Street Smarts, Pop Rock

Will Hit You the Hardest When:

You’re on a different life path than most of the people you grew up with. You choose to follow your heart and your big dreams rather than play it safe and secure. Many people think you’re naive, but you’re living a life you’re proud of.

#32: Gomez - See the World

Filed Under:

Open-Minded, Positive Outlook, Simple Pleasures, Put Your Guard Down, Indie Rock

Will Hit You the Hardest When:

You need a little reminder that it’s the little things that make life beautiful. You don’t want to argue or get crazy; you just want relax and share the love.

*This song isn't necessarily a friend to feminism with the "find an old fashioned girl" line, but it means well. :)

#33: Brothers Osborne - Stay a Little Longer

Filed Under:

Sexual Tension, Keep Coming Back for More, Drunk Mistakes, Can’t Move On, Hooking Up, Confusion, Country

Will Hit You the Hardest When:

You’re craving physical intimacy and romantic connection but you’re not sure if you’re in a place to commit to someone. You can’t decide if it’s the person you want or just the idea of you with them.

#34: Edwin McCain - I’ll Be

Filed Under:

Deep Love, Romantic Partnership, Security, Believing in Love, Great Love, Pure Love, Unconditional Love, Pop Rock, Alternative Rock

Will Hit You the Hardest When:

You want to be the person for someone— everything they need through all the ups and downs in their life. You’re ready to be the partner, lover, teammate, support system, cheerleader, and shoulder to cry on.

#35: Loggins and Messina - Danny’s Song

Filed Under:

Love, Life, Simple Pleasures, Gratitude, Family, Marriage, Happiness, Fulfillment, Folk Rock, 70s

Will Hit You the Hardest When:

You’re simply happy with what you have. You don’t have every single thing you want, but you have everything you need. You have a partner in life and love and you can get through anything with them.

#36: Austin Basham - On the Hunt

Filed Under: Giving Without Getting, Lyrical Magic, Indie, Folk

Will Hit You the Hardest When: You’ve given them everything you have, and you don’t regret it, but they keep taking without giving. You’re starting to realize that your love can’t lead them where they need to go. They need their own love in order to know what to do with yours.

#37: Josh Krajcik - No Better Lovers

Filed Under:

Physical Intimacy, Passionate Love, Sexual Desire, Sexual Partnership, Romance, X Factor USA

Will Hit You the Hardest When:

You feel love for someone else like you never fully knew you were capable of. There’s immense passion and a profound sense of camaraderie, both in general and on a carnal level.

#38: Incubus - I Miss You

Filed Under:

Missing Someone, Longing, Rock

Will Hit You the Hardest When:

You’re feeling the physical pain of missing someone, whether for the first time or the dozenth. You want to tell them, simply, “I just miss you.”

#39: A Day to Remember - If It Means A Lot To You

Filed Under:

Long-Distance Relationships, Missing Someone, Trying to Make it Work, Rock

Will Hit You the Hardest When:

You’re in a long-distance relationship and you’re determined to make it work, but you might be the only one who believes you guys can make it.

#40: Elenowen - No Such Thing as Time

Filed Under:

Love, Bad Timing, Time-Sensitive Relationship, Making the Most of Time, Physical Intimacy, Folk Rock, Duo

Will Hit You the Hardest When:

You’re in a time-sensitive relationship, and time is both your fiercest enemy and biggest savior. You want to get lost in your partner and make the most of every second so you forget that time is running out.

#41: Five for Fighting - 100 Years

Filed Under:

Life, Love, Existential, Beauty of Life, Relationships, Gratitude, Simple Pleasures, Meaning of Life, Putting Things in Perspective

Will Hit You the Hardest When:

You want to feel allllll the feels. Slowly. Think about your life, the time you have, the people you’re surrounded by.

*I rarely let myself listen to this song, because it makes me feel on almost too deep a level. It’s beautiful and powerful and scary, and it’s probably one of my favorite songs of all time.

#42: Goo Goo Dolls - Iris

Filed Under:

Human Connection, Romantic Connection, Deep Understanding, When Someone Just Gets You, Craving Someone, Aching for Understanding, Lost and Found, Rock

Will Hit You the Hardest When:

You want to forget everything that’s going on around you and focus on the person in front of you. You’ve waited your whole life to find someone who just gets you the way you’ve always ached for someone to, and you’re ready to get lost in this reality before the rest of the world reminds you it still exists.

#43: Zac Brown Band - Sweet Annie

Filed Under:

Forever Love, Marriage, Ready to Settle Down, Game-Changer Relationship, Country

Will Hit You the Hardest When:

You’ve found your game-changer. You’ve found the person you want to give up all the bullshit for. No more party lifestyle or sleeping around or feeling empty. You’re ready to commit to forever love and don’t have a doubt in your mind.

#44: Kip Moore - Hey Pretty Girl

Filed Under:

Making a Move, Falling in Love, Finding the One, Marriage, Making Babies, Great Love, Storytelling, Healthy Love, Romance, Country

Will Hit You the Hardest When:

You just need a good example of a solid, healthy relationship and love story. You know what you deserve and can’t wait to experience great love, marriage, and baby(ies).

#45: Daniel Wilson - If You Went Away

Filed Under:

Haunting Love, Losing Someone, Fighting for Love, Selfish Love, R&B, Electronic

Will Hit You the Hardest When:

You can’t deal with the thought of them leaving. Maybe you’re a little selfish. Maybe they need to go live their life. But you just want them and can’t imagine not having them anymore.

#46: Ryan Calhoun - Who We Are

Filed Under:

Self-Awareness, Courage, Self-Confidence, Believing in Yourself, Following Your Heart, Being True to Yourself, Moral Conviction, The Road Less Traveled, Folk

Will Hit You the Hardest When:

You’re not sure exactly where your path is leading, but you’re following your heart and moral conviction. You know you’re doing what’s right for you, and you want the people who care about you to support you and trust your judgment.

#47: Honor By August - Johnny (Pass Me Another One)

Filed Under:

Memories, Mistakes, Reminiscing, Love and Loss, Depression, Sadness, Deep Longing, Loneliness, Heartbreak, Drinking Away Your Problems, Getting Drunk, Drinking to Forget, Missing Someone, Rock

Will Hit You the Hardest When:

You feel utterly lost and confused about what you can do to make the person you love believe in you again. All you want to do is right your wrongs and assure this other person that you’ll never hurt them again and that you’ll be there when they need you. But they won’t give you any more chances.

#48: Sam Palladio - When the Right One Comes Along

Filed Under:

Hopeless Romantic, Waiting for The One, The Fairytale Exists, Country, “Nashville”

Will Hit You the Hardest When:

You’re feeling a little disheartened about the state of your love life and need a reminder that one day you’ll meet someone and just know.

#49: Tim McGraw - Humble and Kind

Filed Under:

Life Lessons, Facts of Life, Humanity, What Really Matters, Simple Truths, Kindness

Will Hit You the Hardest When:

You just need to put things into perspective. You need a simple reminder of the beauty of life and what really matters in it.

#50: John Denver - Take Me Home, Country Roads

Filed Under:

Country Life, Mountains, Simple Pleasures, Beautiful Scenery, Nature, Small Town Life, Love, Family, Truth, Gratitude, Memories

Will Hit You the Hardest When:

You want to remember where you came from-- when you feel lost and lonely, when you’re far from people you love, when you’re homesick, when you’re human. Anytime, anywhere.

Full Spotify playlist:

https://open.spotify.com/user/122224041/playlist/0EV43k3iA04zZ6KMiEQPyp

1,752 views0 comments