Vintage Valentines

vintage valentines
Vintage Valentine

Somewhere in this house, I have a box of vintage Valentines. We moved into our new home six years ago, so I know they are probably tucked away in a box in the attic. One day, I’ll look for them, but not today. I’m so glad I did take some pics of them several years ago))

Vintage Valentines

I went to school in the 1950s so there you have it. An official babyboomer))) On Valentine’s Day, we always had a class party.

Pinedale High School
Pinedale School, Pinedale, MS

Our school was small and there were two grades in each room with one teacher. No teacher’s aide, no moms coming in to help. The one teacher had all of us.

pinedale school
Pinedale High School, First-Grade Class

The Valentine’s party was a big deal! It would always be in the afternoon before school turned out. Everyone rode the bus unless they were a teacher’s child or lived within walking distance of the school. I rode the bus.

In fact, I rode the bus for the entire 12 years! Heck, the first year I went to junior college….I still rode the bus!

On the day of the party, everyone would bring Valentines to school for the kids in your class. This is where my box of vintage Valentines comes from, collected through the years.

The Valentines might be homemade on red, pink, or white construction paper or the store-bought variety. It was not unusual for Valentines to be re-purposed.

The name of the recipient was written on the front of the envelope and the giver’s name was written on the back of the Valentine, usually in pencil. Sometimes you could see a previous name carefully erased so the Valentine could be used again.

school valentine party
Vintage Valentines

Some Valentines had a little screw in the middle so they could be folded to fit in a smaller envelope. There was always a special Valentine for the teacher in a purchased box of Valentines.

I was lucky that my parents were usually always able to come up with a fresh box of Valentines for me to address and take to school. Sometimes it might be unused ones, from the year before, but I never had to erase names and use them again that I can recall. That wasn’t the case with everybody in my class for sure.

Special Vintage Valentines

Large Valentines about 5″ x 5″ could be purchased separately for about 5-10 cents or so. These big Valentines were “very” special if you received one. Typically, they would be from a boy in the class that liked you.

large special valentines
Vintage Valentines

Sometimes the special vintage Valentines would have glitter or a sort of flocking on them to make them velvety and sparkly. They would be a prized possession to the girls.

The Valentine Box

The class would decorate a big box to sit on the teacher’s desk. A slot was cut in the top and once you got to school, you dropped all your Valentines into the box.

We watched that box all day until time for the party. I don’t recall that we had anything to drink at these parties, but we might get a cookie or a piece of candy from the teacher.

The teacher would reach her hand into the box and pull out the Valentines one by one. When your name was called, you walked to the front of the room got your Valentine, and took it back to your desk. It was exciting to rip the envelope open and see who it was from.

And if you got one of those BIG envelopes….well….just wow, that’s all I can say.

If someone really liked you, you might get a sucker taped to your Valentine)))


If you had a boyfriend, the Valentine’s party was a day to look forward to. I had one, the cutest boy in class))) I sort of hate to even write about him now because he passed away a few years ago, but we were a pair in grammar school.

jeannie, pinedale, grammer school
Jeannie & H. M.

This is a photo of us at a school function, we were some sort of King and Queen.

Mother made my dress out of orchid taffeta and netting. It had little sequins and flowers hand-sewn around it.

Daddy had to take me to school that day for pictures because I had been home sick with the red measles! I hope I was past the contagious period!


I can remember being carried to the dinner table by my dad…..I don’t remember if I was too sick to walk or just soaking up the attention. They also made me a bed on the couch so I could stay in the living room, but it had a sheet hung up over me so I couldn’t watch TV. Because, as everyone knows… measles would make your eyes weak if you watched TV. That was a well-known medical fact)))

So, I lounged on the couch with a sheet hanging from the ceiling shielding me from seeing the TV, listening to our favorite family shows like Lassie…Howdy Doody, Ozzie, and Harriett, Father Knows Best, ….and so on.

Time Marches On

Before our middle school, years were over my friend and I went our separate ways. The schools were consolidated and I went to one and he went to another.

I saw him several times throughout our teen years and he was still one of the cutest boys around and a sharp dresser. The trend at the time was pink oxford cloth shirts and pink socks……yellow shirts….yellow socks… blue shirts….baby blue socks… was all the rage.

My next main boyfriend was also the most handsome boy in the community……black hair (Elvis comb back style with sideburns) also with a pink shirt and pink socks….tall and dangerous…..oh my gosh…..he’s in the living room now!

The black hair has turned gray and thinned out with time….he’s still tall….and easy on the eyes……that dangerous spirit has turned into a beloved “Pop” as the grandkids call him…….but, that’s another story for another time)))

More Vintage Valentines

vintage valentines
Vintage Valentine

I noticed on one of the pics that there was a “made in the USA” printed on the Valentine. That’s not something you see so much of anymore, but it needs to be!

old 1950's valentines
Vintage Valentine

The last time I looked through my old Valentines some were from people I hadn’t thought of in years. And some had passed away. Some of the names I could not place and I had to get an old annual out to make the connection. Surprisingly, there were a couple of Valentines from people who I had seen within the last month or so.

My husband has never been one to send special cards, he’s more of a flowers and candy man))

Valentine flowers from husband
My Valentine with My Valentine Flowers))
10 valentine gift ideas
  1. Personalized Gifts: A unique piece of jewelry, engraved items, or something personalized.
  2. Fun Experiences: Tickets to a move, a weekend getaway, or a fun activity like a cooking class.
  3. Love Notes: Handwritten letters or sweet, heartfelt messages. An old-fashioned homemade Valentine.
  4. Time Together: A date night.
  5. Thoughtful Surprises: Gifts that show you’ve paid attention to their interests or hobbies.
  6. Sweets: Box of chocolates, candy, or cookies.
  7. Flowers: Favorite flowers or a beautiful arrangement.
  8. Tech Gadgets: A smartwatch or a cool tech accessory.
  9. Books or Music: By their favorite author or performer.
  10. Self-Care Gifts: A spa gift, bath bombs, or massage.
10 ideas – for those married a while
  1. Car Service: Detailed inside and! Oil changed.
  2. Restaurant: Lunch or dinner at an upscale place.
  3. DIY: A DIY project that you’ve talked about for years.
  4. Housecleaning: By a professional. Get those dust boards!
  5. Garden Gift: Rose bushes or shrubs, set out.
  6. Tools: Personal tool bag with common tools.
  7. Night Out: A friend’s night out! Restaurant and movie.
  8. Clothing: Bombas socks!
  9. Houseplants: Repot all the potted plants.
  10. Security Camera: Home safety system.

I hope you get a special Valentine this year)))

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  1. Thoroughly enjoyed this Vintage Valentine post Jeannie!! With your wonderfully descriptive writing, I felt like I could see that Valentine’s box on your teacher’s desk!! Also loved all the priceless photos, and the vintage Valentine card photos!! Have a great day!!

    1. Thank you so much Bonnie, I’m so glad you visited! And I’m glad I saved those Valentines throughout the years. They were all in one big envelope and several years ago I divided them out and gave my two sisters theirs….I wish now I had just kept them all)))

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