10 Embarrassing Teenage Relationship Moments That Make Us Nostalgic

First relationships can be exciting, but they can also lead to some awkward and cringe-worthy moments. Recently on an online platform, people have shared some of the cringiest things they have done in their first relationships.

1. Junior Year Kiss Mishap

Woman surprised
Image Credit: Shutterstock.

Once upon a time, there was a hopeless romantic who fell for his girlfriend three months before their sophomore year ended. But, when summer arrived, he disappeared without a trace, leaving his girlfriend heartbroken. On the first day of junior year, the romantic thought they were still together and decided to surprise his love with a kiss. However, it didn't go as planned, and the girlfriend's reaction was not what he expected. To this day, the romantic feels embarrassed about his foolishness.

2. Backhanded Compliment

Woman with surprised reaction
Image Credit: Shutterstock.

A brave soul once admitted that they made an incredibly cheesy comment to their girlfriend during their first relationship. The over-eager romantic told his love that he was grateful she wasn't the most beautiful girl in the world, as he would have had to fight off hordes of admirers. The romantic cringes at the thought of ever saying something so cringe-worthy.

3. Cringe-Worthy Love Letters

Photo Credit: Adobe Stock.

According to a soul-baring romantic, the cringiest moment of their first relationship was writing love letters that they thought were deep and meaningful at the tender age of 15. Looking back, the romantic can't help but cringe at the cheesy content of those letters, praying they no longer exist.

4. Overly Persistent Phone Calls

Man giving surprised reaction seeing mobile.
Image Credit: Shutterstock.

A naive romantic started dating his girlfriend, and within a week or two, his love stopped answering his calls at school. Driven by desperation, the romantic called her house six or seven times until her mother finally answered, furious about the constant ringing. Unfortunately, the romantic overheard his girlfriend in the background, referring to him as a “weirdo” and explaining why she didn't want to answer. Hurt and embarrassed, the romantic went to his room and carved his girlfriend's name into the wall with a pen. To this day, the romantic cringes at the memory of his embarrassing behavior.

5. The Dry Mouth Dilemma

Photo Credit: Adobe Stock.

Once, a lovesick soul was walking his girlfriend home, dreaming of sharing their first kiss at her doorstep. However, he couldn't stop licking his lips, worried about a dry mouth, and halfway to her house, his girlfriend suddenly told him to stop. Realizing how creepy he must have looked, the lovestruck soul cringed with embarrassment.

6. Best Friend's Advice

Image Credit: Adobe Stock.

A romantic at heart once confessed to breaking up with his girlfriend because his best friend told him to, even though they were perfectly happy together. The romantic admitted that he idolized his friend and valued his advice above all else, but things got even worse when his friend tried to ask out his ex-girlfriend after their breakup. All of this happened when the romantic was just 14 or 15 years old, and looking back, he cringes at his foolishness.

7. Pizza Hut Proposal

Young beautiful woman with slice of pepperoni pizza screaming laughing on dark pink background
Image Credit: Shutterstock.

An enthusiastic romantic tried to propose to his high school girlfriend after watching Eric propose to Donna on That 70s Show. Determined to recreate the magical moment, the romantic bought a cheap ring from the local Pizza Hut and proposed in front of everyone at school. Sadly, the proposal didn't go as planned, and the romantic can't help but cringe at his attempt to make a TV show moment a reality.

8. Taking a Beating for Love

Photo Credit: Shutterstock.

A brave and chivalrous romantic once tried to defend his girlfriend's honor and got into a physical altercation with three guys. Unfortunately, he ended up getting beaten up, and although he earned some credibility for taking the beating, his girlfriend thought it was too much and suggested they should be friends. Looking back, the romantic cringes at his foolishness.

9. Social Media Love Note

Photo Credit: Shutterstock.

A soulful romantic once posted a video of himself singing Radiohead's “Creep” on social media with the caption “For that special someone” during a break in his first relationship. Looking back, the romantic cringes at how desperate and embarrassing the post was.

10. Papa Roach Serenade

Photo Credit: Adobe Stock.

At the tender age of 17, a lovestruck teenager had a heated argument with their significant other. In an attempt to make amends, they hopped into their car and drove to their partner's house. They played “Scars” by Papa Roach at full blast from their car stereo, hoping to catch their partner's attention. They stood anxiously at the end of the driveway, waiting for their partner to emerge. In hindsight, this lovestruck teenager deeply regrets this cringeworthy attempt to reconcile.

11. Love Confession Gone Wrong

Image Credit: Shutterstock.

The first user in the thread made the mistake of yelling “I love you” to their crush within 24 hours of meeting them in the school parking lot. Looking back, the storyteller admits it was a cringe-worthy move and one that they would never make again. Despite the awkward start, their relationship lasted for a few months, and the storyteller learned a valuable lesson about taking things slow.

Ready to make your first budget?

Enter your email and get the free template


12. Surviving a Car Accident in a Relationship

ultimate international travel checklist
Image Credit: Adobe Stock.

Imagine hitting your girlfriend with your car during your first relationship – that happened to one account holder. While the incident was a complete accident, it left both parties shaken. But, surprisingly, the relationship survived the mishap, and the two remained friends, even jokingly reminiscing about the incident occasionally. Looking back on it, the user cringes at the thought of what could have happened but is grateful that things turned out okay in the end.

13. Awkward First Kiss Attempt

Photo Credit: Adobe Stock.

One dater shares a cringe-worthy moment from their first relationship that they wish they could forget. After their first date, the couple sat in the driveway, and their partner was clearly waiting for a goodnight kiss. However, the user was too scared to make a move and was surprised when their partner leaned in for a kiss instead. In a moment of pure awkwardness, the user licked their lips all the way around with their tongue, imitating Scooby Doo's iconic move with cotton candy in the show's theme song intro. The user even did the “reeheeheeheehee” laugh that Scooby Doo is known for. Looking back, they cringe at the memory and wish they had reacted differently.

14. Inappropriate Behavior in Young Love

Photo Credit: Adobe Stock.

Can you imagine taking laps around the playground and slapping stickers on your partner's behind during your first relationship? That's what one youngster did, and they now realize it was completely inappropriate and embarrassing. Looking back, the individual can't believe they ever thought that was a good idea and cringes at the thought of their behavior. Although the relationship eventually ended, the person learned an important lesson about respecting boundaries and treating their partners with the respect they deserve.

15. Bad Breath and Communication in First Kiss

Photo Credit: Adobe Stock.

First kisses can be nerve-wracking, but when strong-smelling ingredients are involved, things can get even more uncomfortable. One individual recalls their first kiss with their partner, who had just eaten a bacon double cheeseburger with onions. Feeling uncomfortable with the situation, they told their partner they had a previous bad experience with French kissing and asked him not to do it again. While the memory may be cringy, it's also a reminder that communication is key in any relationship.

16. Creepy Crush Tactics

Image Credit: Shutterstock.

Shyness and infatuation can lead to cringe-worthy moves, as one Redditor learned in their first relationship. The commenter was so enamored with a classmate that they never wore their hair up again after the classmate complimented them on looking like a particular celebrity. The Redditor also tried to catch their crush's attention by slipping a note into their locker without signing it and giving them a t-shirt they thought they would like, without revealing who it was from. The situation turned creepy when their crush didn't know who the anonymous gifts were from until a friend pointed it out weeks later. Although the relationship ended after only a day, the user and their former crush reconnected and got married 15 years later. Despite the initial cringe-worthy moves, the story has a happy ending, and the user can look back on their past with a sense of humor.

How I make $11,000 per year renting out my spare rooms?

Get access to my FREE guide now.


17. Grand Gesture Backfires

Photo Credit: Adobe Stock.

An obsessed lover decided to make a grand gesture of their love by getting matching dog tags with their anniversary on them. However, their partner didn't share the same level of enthusiasm for the gift, and the lover secretly felt sad as the dog tags were left untouched. After some reflection, the lover realized that their grand gesture may have been too much, too soon. Although the relationship didn't last, the lover learned a valuable lesson about respecting their partner's boundaries and not forcing their feelings onto others.

18. Overzealous Planning for a Crush

Photo Credit: Adobe Stock.

When it comes to love, sometimes we can get too far ahead of ourselves. One commenter admitted to making a cringeworthy move before officially dating their crush. After hearing her mention her desire to visit New Zealand, the user priced plane tickets and lodgings for a honeymoon in New Zealand. They even told their crush about the plans, hoping to start saving early in case things worked out. Although the relationship lasted only two months, the individual still cringes at the memory of their overzealous planning.

19. Cheesy Gift Embarrassment

Photo Credit: Adobe Stock.

It's the thought that counts, right? Well, one young lover learned the hard way that sometimes even the best intentions can lead to cringeworthy moments. Their mother went above and beyond by purchasing custom airbrushed shirts with a design of two people kissing and their names on them. Although the gesture was sweet, the person felt embarrassed as they had not discussed the idea with their girlfriend beforehand. Despite not knowing how their girlfriend felt about the shirts, the individual cringes at the memory of the overly cheesy gift.

20. Vomit After a Kiss Attempt

Photo Credit: Adobe Stock.

Young love can be so awkward at times. One lover recalls a particularly embarrassing moment when their boyfriend's dad dropped them off at home. Nervousness got the best of them, and they leaned in for a quick peck on the cheek. Unfortunately, as soon as they pulled away, they vomited all over themselves, thanks to some fajitas they had eaten earlier. This remains a cringe memory that they would rather forget.

Does “Male-Privilege” Exist? Here Are 10 Reasons Perhaps Not

Photo Credit: Adobe Stock.

The men and women of Reddit share what they believe are the worst things about being a man.

10 Red Flags That Say “Don't Date Me, Run!”

Photo Credit: Adobe Stock.

The Reddit community compiled a list of red flags in both men and women that should be avoided.

“Barbie Was Right” 10 ‘Girly' Habits Men Should Pick Up As Well

Photo Credit: Adobe Stock.

There are plenty of things, like skincare and moisturizing, that women already do. But why can't men do them too? The Reddit community shared some things they believe men should start doing that women already do.

Relationship Buzzkills: 10 Things Men Can't Stand Hearing from Women

Photo Credit: Adobe Stock.

Some phrases are overused. Some are just plain annoying. The men of Reddit have come together to share what phrases they hate hearing from women the most.

10 Foods You Should Never Order On A Date

Photo Credit: Shutterstock.

Going out on a date can be a nerve-wracking experience, and what you choose to order can play a significant role in how the night goes. One Reddit thread asked the question, “What's the worst food to order on a date?” The thread received thousands of responses, and here are ten of the most popular answers.

[mashshare]

How I make $11,000 per year renting out my spare rooms?

Get access to my FREE guide now.