So this happened… 12 too-cute vintage engagement stories from the ’20s

1920s couple - engagement stories

Note: This article may feature affiliate links, and purchases made may earn us a commission at no extra cost to you. Find out more here.


The question “How did he propose?” was asked in a series of nationally-syndicated newspaper columns during the early 1920s. Here’s a selection of some of the best engagement stories — from the sweet and simple to the too-cute-for-words.

How did he propose 100 years ago, women shared their engagement stories

1. First and last

Trying to entertain a young man one evening, I showed him our old photo album.

Pointing to the picture of a sweet-faced young woman I said, “This pretty woman was mother’s dearest friend years ago when we lived in the east. She had an only child, a nice little boy of whom we have heard nothing since the days when he was my first little sweetheart.”

He seemed spellbound, and taking my hands in his said, “Well, this is a small world. That is my mother’s picture, and if I was your first sweetheart, why can’t I be your last? I’ll promise you’ll never lose me again.”

2. Quite by accident

I had been going with Bob for two years, and knew he never went with another girl, although he had many girl as well as boy friends. For two months, he had been telling me how much he cared for me.

It was one night in early summer. We were riding along a beautiful country road. He drew me close and kissed me and said, “Sweetheart, will you…” Just then, another car came whirling along and he was interrupted. Thinking I knew what he was about to say, I said, “Of course, I will, darling — as though I could ever marry another man.”

In about two weeks I received my diamond ring. We have been married two years now, and just the other night, he asked me if I remembered the night he proposed.

I did, and he said, “I had been trying for a long time to gather the courage to ask you to marry me, but what I was really going to ask you that night was if you’d go to the prom with me or not.”

We both had a hearty laugh.

3. They ran away

One evening when I was out with a friend, I told him I always had a desire to run away and be married for months before anyone knew anything about it. He said, “So would I, kid — let’s run away and get married.” We did, and he has proven to be a good husband.

4. Short and tall

We first met at a wedding dinner, where the bride was my best friend. He was the wartime buddy of the bridegroom. The bride was diminutive like myself, and the bridegroom tall and handsome like his friend. In commenting on the attractive couple the newlyweds made, I remarked that I liked to see a tall man pick a small girl, because he looked as if he was capable of protecting her.

The bridegroom’s buddy and I saw much of each other after that. And then one night, he suddenly took my face between his two hands, and looking into my eyes, asked, “Am I tall enough to look capable of protecting you?”

Now, what answer, pray tell, could I make to that query?

Shortly afterward, we, too, were married.

Dance with couples and fancy dresses in the 20s - 1922

5. A typed engagement story

I bad for a long time been accepting the attention of an old high school friend who was endeavoring to make a living by fiction and songwriting. Since he was rather inclined to be silent when in company, and since be had not succeeded in selling any of his work, my family looked with disfavor upon him.

One day while I was returning from work and passing his home, his sister called me in, saying her brother had two stories and one song purchased that day. I found him at his typewriter, wild with joy.

“Two in one day, and they told me to come back with more at the song publisher’s, so I’m turning out another now,” and he looked at the typewriter.

Confusion came over his face. I leaned toward the typewriter to read the manuscript. Then I blushed. He had just finished the title in copying from another sheet. “Marie” was the title. His hands went to the typewriter. He added a comma after the title, and then the words “Will you marry me?”

Haltingly, I typed “Yes.”

MORE: Here’s what newly-engaged couples need to know (1921)

6. Wanted a monopoly

For some time I rather thought the young man with whom I was keeping company was going to propose. However, although I liked him quite well, I wasn’t ready to say I cared enough to marry him.

One evening, we had been driving, and he said something about making an engagement for another time. I told him I had a previous engagement for that evening. I told him when he protested that I liked him, but I also liked to go to places with other men, and didn’t want one man to claim all of my time. I’ll never forget what he said.

He put his arm around me and said, “My dear, I more than like you. I love you, and I want to be the only man in your life.”

I thought then I didn’t care, but soon found out I did, and we were married in two months. That was five years ago, and we still more than like each other.

7. More beautiful in white

I was bridesmaid at a wedding, and wore a pink dress. After the ceremony, a young man who was present asked me to ride home with him in his car. When we reached home, I invited him in.

In the parlor, he seized my hands. and stammered, “Y-you don’t look good in pink…you’d look beautiful in white, with a long veil, you and me, and the preacher, and just our folks, and not a big crowd like the wedding today.”

That was the first time in my life I had ever had any prospect of looking beautiful, so I accepted him on the spot.

8. It usually lands ’em

When I was a young girl, I never allowed a boy friend to be sentimental or even kiss me. (This may seem exaggerated to youthful readers.)

I had been going with a young man who had been repeatedly refused a goodnight kiss. One evening, he asked me why I refused. I told him I would not permit any young man to kiss me unless I was engaged to him.

Well, he kissed me that very night.

Cute couple from 1920

9. Passing the time

My proposal was quite unusual. It was always understood between Harold and me that at some time we would be married, or at least we thought it was understood.

One afternoon he telephoned we ask me if I cared to go to a movie.

“Why, certainly,” was my answer.

When we arrived in the city we had some time to pass away, so we went window shopping.

After that, I said, “What shall we do now?”

He said, “Let’s get married.”

It was a shock to have him ask it so suddenly, as I had always wanted a formal proposal. But I said, “All right.”

I really didn’t think he was serious. Nevertheless, we started for the Justice of the Peace, and as we were going up the stairs, I began to feel faint and was thinking that my nerve was almost to fail me. Then he took my arm and led me to a room. To my surprise, he brought forth a marriage license and a ring, and there before four witnesses, we were united in matrimony.

We have lived five happy years of it so far, and are not dreading the remaining ones in the least.

ALSO SEE: 29 old-fashioned wedding superstitions (1921)

10. A leap year engagement story

I attended a public concert, at which the chairman explained that every piano or violin represented some thought, idea or story. At the end of a certain number, he asked the audience to tell him of their mental reactions. I had this to say: “I felt as one would while listening to a proposal of marriage.” General laughter ensued.

Leaving the hall at the end of the concert, I overheard a pretty girl commenting about me like this: “I wonder if this young man was really ever proposed to? This is 1920, a leap year!”

I turned around and smiling back at the smiling girl, answered: “No, young lady, but I reckon I would give you a chance!” This flirtation led to courtship, which culminated in our marriage, spelling happiness to both of us.

11. Engaged thanks to a bird

It all happened on account of a robin. It was Sunday afternoon — he was taking me home from a big day at an amusement park. Just a few steps before reaching home, I saw on the sidewalk a poor robin with an injured leg. I knelt down to help it, passing some remark about its mate. Then I expressed my sorrow for it.

George asked me if I really felt sorry for anything alone like that. I told him I did. He said I should feel more sorry for him, as he was getting old and didn’t have a mate.

“Well,” I suggested, “why don’t you hunt for one?”

“I don’t have to hunt. I’ve found her already,” he smiled.

Woman in a wedding dress from 1922

12. Dreams come true

I never will forget my husband’s proposal. We were sitting on the front porch of my home and had been talking of dreams. He told me he had dreamed of me the night before. He dreamed we were on a train going away to be married, and he even dreamed of the place we intended spending our honeymoon. He said he was awfully disappointed when he awoke and found it was only a dream.

He said he wanted it to come true, and asked me if I wanted it to come true also. Of course, I admitted I did, for I knew he had been wanting to propose to me, but didn’t know how to start it.

I also knew that he made up the dream at the time, and he has since admitted that he did.

Vintage wedding book - Something Old

PS: If you liked this article, please share it! You can also get our free newsletter, follow us on Facebook & Pinterest. Thanks for visiting and for supporting a small business! 🤩 


You might also like...

The fun never ends:

Comments on this story

Leave a comment here!

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.