Songs about encounters with ex-lovers, or wistful songs about old flames

Recently, I had a chance encounter with a former lover. She recognized me first and tried to catch my eye across a crowded room. I sat stupidly wondering why this beautiful woman kept staring and grinning broadly at me until finally, finally, it dawned on me who she was.

It went like you might expect, we embraced joyfully, and then spent a few minutes catching up. She: married with two kids. Me: still roving like a pilgrim. We talked about the fun we’d had together, and laughed about the old times, and then shared sad news of relatives and friends lost since last we’d met. And our eyes stayed locked together, and we talked and talked some more. And after a while, we parted. And her eyes grew red and full as she turned to walk away, and I noticed her jaw trembling, and well, I didn’t feel so good myself.

There is something really poignant about encountering an old flame after a few years have passed. Something about seeing how you’ve both changed over the years, and thinking about your time together and the things that drove you apart, and all the bittersweet feelings, and most of all wondering about what might have been if your lives had gone in the same direction instead of diverging…

And I got to thinking about all the songs written on this very topic, and then I came here to the Dope, to share my experience and to ask y’all to share your favorite songs about encountering a past lover, or songs of wistful remembrance of lovers long gone.

I’ll start it off with a video clip:

Still Crazy After All These Years - Paul Simon

I mentioned this one in the sad love song thread, but it applies here, too.

Back 2 Good by Matchbox 20

Unaswered Prayers by Garth Brooks (a great song)

In Your Wildest Dreams by the Moody Blues

and only if you are not diabetic My Eyes Adored You by some talentless hack.
Happy Together by the Turtles (some say)

Dan Fogelberg’s “Same Old Lang Syne.”

According to an acquaintance, in concert Fogelberg claims that the song is based on a real encounter, and that in real life, the chance meeting with an “old lover/In the grocery store” ended up with them in bed.

Now I feel dirty all over.

Distantly in Love by Jimmy Buffett (1983)

One verse sums up the problems of lost loves quite nicely:

“I heard it from a friend of ours I saw in Timber Bay
You had a new lover who had stolen you away
That could be the reason that I never got in touch
May present slight problems if he loves you half as much”

What Might Have Been - Lonestar (but I thought it was Shenandoah)

Sample lyrics -
That same old look in your eyes
It’s a beautiful night, I’m so tempted to stay
But too much time has gone by
We should just say good bye, and turn and walk away…

Sometimes Love Just Ain’t Enough - Patti Smith and Don Henley

Sample Lyrics -

And there’s no way home
when it’s late at night and you’re all alone.
Are there things that you wanted to say?
And do you feel me beside you in your bed,
there beside you, where I used to lay?

And there’s a danger in loving somebody too much,
and it’s sad when you know it’s your heart they can’t touch.
There’s a reason why people don’t stay who they are.
Baby, sometimes, love just ain’t enough.

Nobody Knows - Kevin Sharp

Sample lyrics -
I pretend that I’m glad you went away
But these four walls close in more everyday
And I’m dying inside
And nobody knows it but me

One more -

Look Away - Chicago

Sample lyrics -

When you called me up this morning,
Told me bout the new love you found,
Im said Im happy for you,
Im really happy for you.
Found someone else,
I guess I wont be coming round.
I guess its over, baby;
Its really over, baby, whoa…
And from what you said
I know you’ve gotten over me;
Itll never be the way it used to be.
So if its gotta be this way,
Dont worry, baby, I can take the news okay

I’m not sure I’d call this song wistful, but Black by Pearl Jam is a powerful song about a lost love.

If You See Her Say Hello by Bob Dylan (only for the strong)
Looks Like We Made It by Barry Mannilow

Centerfold J. Giles Band

Joan Baez’s Diamonds & Rust

Well speaking of Pearl Jam, I’d say Elderly Woman Behind The Counter In A Small Town (video clip) fits the bill (in sort of an elliptical way):

My God, its been so long
never dreamed you’d return
But now here you are, and here I am
Hearts and thoughts they fade…away…

If You See Her, Say Hello - Bob Dylan


"If you see her, say hello, she might be in Tangier
She left here last early spring, is livin’ there, I hear
Say for me that I’m all right though things get kind of slow
She might think that I’ve forgotten her, don’t tell her it isn’t so.

We had a falling-out, like lovers often will
And to think of how she left that night, it still brings me a chill
And though our separation, it pierced me to the heart
She still lives inside of me, we’ve never been apart.

If you get close to her, kiss her once for me
I always have respected her for busting out and gettin’ free
Oh, whatever makes her happy, I won’t stand in the way
Though the bitter taste still lingers on from the night I tried to make her stay."

Paul McCartney has what must be the mother of all wistful, sad songs about encounters with an old flame. It’s called “I’m Carrying” from the “London Town” album. It’s so powerfully sad, it can still make me cry, like it did the first time I heard it. I’ve often wondered if it was about Jane Asher. I’ve also wondered what Linda thought about that song, because it is so obviously not about her. I hope you can check it out.

Dylan’s “Positively 4th Street” could be interpreted as being about an encounter with an ex-lover, but it’s definitely not wistful.

Taxi, Harry Chapin

There was not much more for us to talk about,
Whatever we had once was gone.
So I turned my cab into the driveway,
Past the gate and the fine trimmed lawns.
And she said we must get together,
But I knew it’d never be arranged.
And she handed me twenty dollars,
For a two fifty fare, she said
“Harry, keep the change.”
Well another man might have been angry,
And another man might have been hurt,
But another man never would have let her go…
I stashed the bill in my shirt.
I know that’s a lot of the lyrics, but it’s a long song so they’re actually a small percentage.

I’m not sure this fits the bill, but I thought of
The Last Day of Our Acquaintance, by Sineád O’Conner right away.

I know you don’t love me anymore
You used to hold my hand when the plane took off
Two years ago there just seemed so much more
And I don’t know what happened to our love
Today’s the day
Our friendship has been stale
And we will meet later to finalize the details

The one that really caught me off guard the first time I heard it was
Most of the Time, by Bob Dylan.

Most of the time
My head is on straight,
Most of the time
I’m strong enough not to hate.
I don’t build up illusion 'till it makes me sick,
I ain’t afraid of confusion no matter how thick
I can smile in the face of mankind.
Don’t even remember what her lips felt like on mine
Most of the time.

Damn you. I was going to say that, but the board shut me down.

I’ll tell you why baby’s crying… Sigh.

And Harry’s “WOLD” isn’t about a chance encounter, since the guy calls his former lover on the phone, but it’s still all about lost love:

OK, honey, I see
I guess he’s better than me
Sure ol’ girl, I understand
You don’t have to worry, I’m such a happy man.

Oh yeah. Here’s a good video clip of that one.

I second Bob Dylan’s "Most of the Time."

Also “I Miss You” by Randy Newman immediately came to mind when I read your post. It’s a very simple, sweet ode to his ex-wife, long after they have gone their separate ways.

I’ll second or third the Dylan song (“If you see her”) and add “We Just Disagree” recorded by Dave Mason, words & music by Jim Krueger.
The lyrics end…“So let’s leave it alone 'cause we can’t see eye-to-eye There ain’t no good guys, there ain’t no bad guys There’s only you and me and we just disagree …” It’s so true, so bittersweet

Don’t Cry, Joni by Conway Twitty