My Greatest Mistake
The Ink Spots Lyrics


Jump to: Overall Meaning ↴  Line by Line Meaning ↴

My greatest mistake
was falling in love,
falling in love with you.
My greatest mistake
was dreaming of you
and thinking my dreams
would come true.
It was easy to see
you never loved me,
though I hoped and
I prayed
someday, it could be.
My greatest mistake,
my greatest heartache
was falling in love
with you.
Darlin',
you know my greatest mistake
was falling in love.
And I mean,
falling in love
with a beautiful gal like you.
You know,
I made another mistake.
Know what that was?
Just dreamin' of you
and being foolish enough to think
that all of my dream
was bound to come true.
You know, it should have been easy for me to see
that honey, ,
you never loved me.
'Course, I hoped and I prayed
that maybe someday
it could be.
My greatest mistake,
my greatest heartache




was falling in love
with you.

Overall Meaning

The Ink Spots' song "My Greatest Mistake" is a bittersweet tune about the regrets of a man who fell in love with someone who never loved him back. The lyrics express the singer's feelings of hurt and disappointment, but also his willingness to acknowledge his own role in his heartbreak. He admits that his greatest mistake was dreaming and hoping that his love would be reciprocated when it was clear that it never would be. He also acknowledges his own foolishness for not realizing this sooner.


Despite the sad message of the song, it also leaves a sense of closure for the singer. He has accepted that his love was unrequited and that he must move on with his life. The use of the word "darlin'" suggests that he still cares for his lost love, but he has come to terms with the fact that they can never be together. Overall, the lyrics are a poignant expression of the pain and regret that come with unrequited love.


Line by Line Meaning

My greatest mistake
Acknowledges that the singer has made a significant error


was falling in love,
The mistake was to fall in love with someone


falling in love with you.
Specifically, the mistake was to fall in love with the person being addressed


My greatest mistake
Reiterates the mistake


was dreaming of you
Another mistake was to fantasize about this person


and thinking my dreams
The mistake was to believe that dreams can be a reality


would come true.
Specifically, that this person would love the singer back


It was easy to see
The following was obvious


you never loved me,
That this person did not love the singer back


though I hoped and
Despite the singer's optimistic outlook


I prayed someday, it could be.
The hope that one day this person could love the singer back


My greatest mistake,
Restates the mistake made


my greatest heartache
The emotional pain caused by this mistake


was falling in love
This mistake specifically involved loving someone


with you.
The person this song is addressed to


Darlin',
Term of endearment directed at the person being addressed


you know my greatest mistake
The person being addressed is already aware of the mistake


was falling in love.
Restated that the mistake was to fall in love with someone


And I mean,
Emphasizes the importance of what is about to be said


falling in love
Reiterating that the mistake was to love someone


with a beautiful gal like you.
Specifically, that the mistake was to love this particular beautiful woman


You know,
Assuming that the person being addressed already understands the following point


I made another mistake.
Acknowledging a different mistake was made


Know what that was?
Asking if the person being addressed can guess what the mistake was


Just dreamin' of you
The mistake was to have fantasies about this person


and being foolish enough to think
Acknowledgment that this was an unwise assumption


that all of my dream
Assuming everything the singer dreamed about would come true


was bound to come true.
That all of the singer's dreams would be made real


You know, it should have been easy for me to see
The singer admits that they should have realized sooner


that honey, ,
Another term of endearment directed at the person being addressed


you never loved me.
Reiterating that the person being addressed did not love the singer back


'Course, I hoped and I prayed
Despite that, the singer still hoped and prayed for a different outcome


that maybe someday
The hope that at some point in the future


it could be.
This person could love the singer back


My greatest mistake,
Repeating the mistake made


my greatest heartache
Reiterating the emotional pain the mistake caused


was falling in love
Again, emphasizing that the mistake specifically involved loving someone


with you.
Reiterating the person this song is addressed to




Writer(s): Jack Fulton, Jack O'brien

Contributed by Tyler K. Suggest a correction in the comments below.
To comment on or correct specific content, highlight it

Genre not found
Artist not found
Album not found
Song not found

More Versions