80s and 90s Preferences, Imagines & Headcannons

𝕖𝕞𝕓𝕒𝕣𝕣𝕒𝕤𝕚𝕤𝕚𝕟𝕘 𝕥𝕙𝕚𝕟𝕘𝕤 𝕪𝕠𝕦'𝕧𝕖 𝕔𝕒𝕦𝕘𝕙𝕥 𝕙𝕚𝕞 𝕕𝕠𝕚𝕟𝕘

ℝ𝕚𝕧𝕖𝕣 ℙ𝕙𝕠𝕖𝕟𝕚𝕩

I was dating River Phoenix for a few weeks when something embarrassing happened. We were at a fancy restaurant, enjoying our meal, when I noticed River fidgeting in his seat. At first, I thought he was just uncomfortable, but then I saw what was really going on. He had accidentally tucked his shirt into his underwear!

Trying to keep a straight face, I discreetly leaned over and whispered in his ear, "River, your shirt is tucked into your underwear." He looked horrified and quickly untucked his shirt. I couldn't help but laugh at the situation. It was just so unexpected and funny.

From that day on, I always made sure to check River's outfit before we went out. He was a great sport about it and we laughed about the incident for weeks. It just goes to show that even the coolest, most talented and handsome guys can have their embarrassing moments.

ℂ𝕠𝕣𝕖𝕪 ℍ𝕒𝕚𝕞

It was the early 90s and I was dating Corey Haim. We were young and in love, and everything seemed perfect. One day, I decided to surprise him by coming over to his place unannounced. I thought it would be a romantic gesture, but what I saw when I walked in was anything but romantic.

There he was, my beloved Corey Haim, standing in front of the mirror in nothing but his underwear and a cowboy hat. He was singing into a hairbrush, pretending to be a country music star. I couldn't help but burst out laughing at the sight.

At first, he was embarrassed, trying to explain that he was just goofing around and didn't think anyone was home. But then he started to get into it, twirling around and serenading me with his terrible singing voice. I couldn't help but join in, belting out the words to a Garth Brooks song.

From that moment on, it became our little inside joke. Whenever we were feeling down or needed a laugh, we would put on our cowboy hats and have a sing-along. It was silly and embarrassing, but it was our thing.

Looking back on that moment now, I can't help but smile. It was a bizarre and hilarious moment, but it was also a reminder that sometimes the most embarrassing things can bring people closer together. And hey, at least we looked pretty damn good in those cowboy hats.

ℂ𝕠𝕣𝕖𝕪 𝔽𝕖𝕝𝕕𝕞𝕒𝕟

It was a beautiful summer day and I was spending time with my then-boyfriend, Corey Feldman. We had been dating for a few months and everything was going well. We decided to take a walk in the park and enjoy the sunshine.

As we were walking, I noticed that Corey seemed to be fidgeting with something in his pocket. I didn't think much of it and assumed it was just his phone or keys. However, as we sat down on a bench to rest, I saw something that left me feeling incredibly embarrassed.

Corey had been fidgeting with his underwear, adjusting it in a way that was very obvious. I couldn't believe what I was seeing and immediately looked away, feeling mortified. I tried to act as if I hadn't seen anything, but it was too late.

Corey noticed my discomfort and asked if something was wrong. I didn't know what to say and just mumbled something about feeling hot. We got up and continued our walk, but I couldn't shake off the embarrassment.

From that day on, I always made sure to look away if I saw Corey fidgeting with anything in his pockets or clothing. It was a small moment, but it left a lasting impression on me. I couldn't help but feel embarrassed every time I thought about it. But, looking back on it now, it's just a funny memory from our time together.

𝕄𝕒𝕥𝕥 𝔻𝕚𝕝𝕝𝕠𝕟

It was a warm summer evening and Matt Dillon and I had decided to take a stroll in the park. As we were walking, we stumbled upon a group of kids playing with a frisbee. Matt, being the sporty guy that he is, offered to join in the game. He took off his shirt and started playing with the kids.