Image Credit: Freeform/The CW/Paramount

10 Nostalgic TV And Movie Boyfriends Who Will Def Give You The Ick Now (Sorry)

As we get older, it’s important that we learn to admit when we were wrong. It can be hard to admit this, but it’s the only way to mature and slay in the present; this is needed more than ever when it comes to TV and movie boyfriends.

We were so delulu back then, falling for the love interest as hard as the plain pick-me girl in a baby tee. We fooled ourselves into thinking that Nate was attractive, Dean was just passionate, and Ezra was romantic. Yuck.

It’s time to give ourselves a big dose of reality and admit that we were so fucking wrong. 

1. Nate in Gossip Girl

Image Credit: The CW

Obviously, I was a Chuck girlie with my entire heart, but I have to shamefully confess that I did find Nate attractive as well. Can you blame me? Those baby blue eyes, the pearly white grin, the smize that would make Tyra squeal; he was built to tear us down. Nate was the Trojan Horse of my libido.

I thought he was an attractive guy, not only that, but a good guy. Looking back now, I can see that Nate was the absolute worst. Like I hated Dan, don’t get me wrong, but Nate is also terrible. He actually thinks he’s a good guy and yet he does such shady things. He feels so entitled to all of the girls, and gets so pissy whenever they date someone else, even though he’s also working his way through the friend group. THE DOUBLE STANDARDS!!!

Some of Nate’s worst crimes:

  • Dating Jenny. Enough said.
  • Cheating on Blair with her bestie, Serena, and then pursuing Serena when she returns from boarding school!!! Are you FOR REAL?
  • Hooking up with married older woman Catherine, and then trying to make her jealous like a pathetic schoolboy (WHICH HE WAS AT THE TIME!!)
  • Dating Sage who is literally in high school, even when he discovers her real age. Like ew, so younger and older women? Also, his ex Serena is dating Sage’s dad at the time. Make it stop.

The list goes on and on. I will say he has great hair, so drop that hair care routine and then leave my brain, you jerk.

2. Lucas in One Tree Hill

Image Credit: The CW

A canon event like no other is starting to watch One Tree Hill because Chad Michael Murray is so hot, and then realizing that his character is the literal worst. Like he is portrayed as the protagonist and victim of the show, when he is legitimately a terrible person. I’ll acknowledge that the way his dad treated him sucks, but he takes it out on everyone, including his sweet, sweet Mom. A lot of the characters in this show were agonizing, except Brooke who I ADORE. Call me, girlie.

Some of Lucas’ worst crimes:

  • Cheating on Brooke with her best friend Peyton. Like bad enough to cheat on the goddess Brooke but with her BEST FRIEND!!! MULTIPLE TIMES! You were lucky to have her and I’m glad she discovered what a trashbag you are.
  • That haircut in the final season.
  • Being such a jerk to Hailey. Would it kill you to support your best friend who is ALWAYS there for you? Especially how rude he was when she became a cheerleader. You’re a basketball player, why is it so different?? You date cheerleaders! You date multiple of them at the same time!
  • Generally leading every woman on and yet slut shaming them. He used Rachel to make Brooke jealous, he dated Anna despite not being over Brooke, and he pingpongs between Brooke and Peyton. Yet when Brooke thinks she is pregnant, he has the audacity to ask if she is actually sure it is his.

You are canceled, Lucas Scott.

3. Michael in The Princess Diaries

Image Credit: Disney

I am still holding on to desperate hope for more The Princess Diaries movies. I want to move to Genovia immediately, get me the fuck out of here. But while I adore these movies, it was quite a shock to go back and rewatch the first one. I was confronted with the fact that Michael is… awful?!?!?!

In my head, he was this total heartthrob and I remember being so happy when they ended up together. But he’s such a judgmental and moody snob. Why was Mia/Princess/Anne slumming it with him? It’s a relief when she moves on to Nicholas in the next film – how do we feel about Chris Pine again?? Is he a good or bad Chris?

Some of Michael’s worst crimes:

  • Thinking he was a total rockstar with groupies, sir, wake up.
  • He put M&Ms on a pizza. Call the police immediately.
  • People claim he was into Mia before her glow up but like he had enough time and nothing had happened??? He also chose not to make a move. Then he gets all threatened when she emerges from her cocoon, clearly he can’t handle a girlboss.

Apparently, the actor has said he’s interested in being in the third film if it happens, and all I can say is please no. I don’t want Mia to take steps backward. He is not the true king of Genovia.

4. Dean in Gilmore Girls

Image Credit: The CW

Why did I used to think Dean was hot and a good guy? Somehow I blamed Rory for how the two of them turned out. Like I thought he was passionate when he’d yell at her. Looking back, I’m thinking my parent’s divorce fucked me up more than I initially realized…

Some of Dean’s worst crimes:

  • Being grossly old-fashioned and thinking women should make their hubby dinner while they earn the bread. But oh, monogamy isn’t his thing I guess since he cheats on his wife with Rory, ok sure!!!
  • Being SO NEEDY. Like he calls Rory 14 times when she won’t answer, he refuses to let her enjoy a night alone, and he dumps her when she won’t say “I love you” after three months. If I am clingy then this man is literal velcro.
  • Trying to get in the way of Rory becoming a girlboss. He won’t let her study, he demands all of her time and won’t support her college ambitions. 

I’m not Team Dean, Team Jess, or Team Logan, I’m Team GO AWAY RORY!

5. Austin in A Cinderella Story

Image Credit: Warner Bros.

Chad Michael Murray, what are you doing here???? It seems like this Hollywood heartthrob of our youth played some rather problematic love interests. 

Now I recognize that this might be a bit more of a controversial take, and I accept that I may not be in the majority here, but just hear me out. 

He was so gorgeous and sweet enough, but he was just SO PASSIVE!! Like I get your dad is controlling but come on. He also watched Sam get humiliated and did nothing. Then a single (albeit hot) kiss in the rain is supposed to fix everything? Also, any guy that writes poetry is a red flag, sorry I don’t make the rules.

Some of Austin’s worst crimes:

  • Not recognizing Sam in a flimsy little mask? I know this is the whole concept of Cinderella but it makes no sense. He went to school with her. She served him regularly in the diner. It was a tiny mask. Does he need glasses?
  • Being friends with people who are rude to wait staff. If you don’t tip or say please, we don’t eat together. He dated Shelby for a while clearly and knew she was awful, that says a lot about his personality.
  • His screen name is “Nomad”?????? Need I say more??
  • HE DIDN’T STAND UP FOR HER DURING THE SKIT! He just sat there! Even if you’re not equally a part of this or in love with her, you don’t just watch someone being roasted like that by YOUR ex-girlfriend. 

That rain won’t wash away all of your crimes, Austin, and I need more evidence that you’re actually a decent guy. Also, get a better screen name, even if it’s FootballBoy69.

6. Raymond in Aquamarine

Image Credit: 20th Century Fox Film

We don’t talk about this film enough. I had it on DVD and watched it dozens of times. It all just seemed so legit to me. Like real starfish earrings? Big slay and definitely not animal abuse in the slightest.

But while the romance of this film isn’t the biggest plotline (it’s about 🌈🌈FRIENDSHIP🌈🌈), it does matter as this is the whole reason Aquamarine wants to stick around. Like she is so besotted with Raymond that she won’t go back to the ocean where I’m sure there are way hotter mermen.

Some of Raymond’s worst crimes:

  • His name. I know it’s not his fault, but I just can’t imagine saying that name in a sexual situation, sorry!! Try to moan the name ‘Raymond’, try it right now!
  • When he gives Claire and Hailey those awkward kisses and it feels like a forty-year-old uncle kissing his nieces. Why? It was so patronizing ew.
  • Being so oblivious. This man did not have two brain cells to rub together.

Amazing film with a wet towel of a love interest (pun most certainly intended!!!).

7. Ross in Friends

Image Credit: NBC

Okay, while none of us were truly, madly, deeply lusting after Ross (at least I think), we all seriously shipped him with Rachel. I mean, he was her lobster! They were end game, right? I thought he was a good guy, and a good boyfriend, and I desperately wanted them to end up together. 

But rewatching Friends, I’m forced to admit that Ross is a terrible guy, and an even worse boyfriend. He and Rachel are not good for each other, and it’s kind of a shame they end up together in the end. I’m sorry!!!!

Some of Ross’ worst crimes:

  • SLEEPING WITH THE GIRL FROM THE COPY SHOP! YOU WERE ON A BREAK NOT BROKEN UP. You should’ve discussed the terms of your break first, e.g. can you sleep with other people? This is NOT okay. My ex thought it was but then again he also cheated on me, sooooooo…
  • Dated a student, Elizabeth. Said Rachel’s name at the altar. Kissed Charlie when she was dating Joey. Dumped Bonnie for shaving her head. HE IS NOT A GOOD GUY.
  • He tried to kiss his cousin??? Do we all remember that episode? 
  • He never supported Rachel’s career or took it seriously. Made her not go to Paris for an amazing opportunity to be with him. He should’ve gone with her to Paris, they have museums there. Like okay, he has a son in the U.S. but he never sees Ben anyway, and Emma is his kid too. 
  • He made a sex tape of him and Rachel (supposedly accidentally) and then kept it. 


Okay, I’ll leave it there but trust me, I have more examples. I am such a Rachel girlie and I think she deserved so much better than Ross.

8. Ezra in Pretty Little Liars

Image Credit: Freeform

Why did we ever think it was okay for a teacher to date his student? Not only okay, but we SHIPPED it?! We were fully here for it. I convinced myself that it was romantic. I don’t care if they met before he knew she was his student, he then realized!!! Aria was 16 and Ezra was 22 when they started. EW! People are like it’s not his fault he fell for her before he knew – THEN HE FOUND OUT! SO STOP IT! END IT!

Some of Ezra’s worst crimes:

  • Statutory rape. Sorry, I’m going to call it what it is. This is not okay. Girlies in high school, if a guy is too old to legally date you, then it’s weird for him to keep wanting you!! Also, it’s not the first time as he also dated Ali first. Repeat offender.
  • He joins the A-Team which is hellbent on destroying his ex-girlfriend’s life. He says it is to write a book about Ali but like there are better ways to achieve this. Also being a writer in general is a red flag – I say this as one, don’t date us!
  • He’s possessive and creepy, and on a show like Pretty Little Liars, that is really saying something.

This is not romantic. This is not cute. This is not goals.

9. Dylan in Modern Family

Image Credit: ABC

Okay, I’m not sure if any of us really adored Dylan, but at least we found him lovable and attractive. Now I don’t even find him those things. He’s just such a caricature of a cool guy and I think it’s such a shame Haley ends up with him! She dated so many better guys and yet he kept returning like a rash.

Some of Dylan’s worst crimes:

  • He sang a song about fucking Haley to her family. Like time and place, please. I don’t care if it is ART, it’s inappropriate. I will reluctantly admit that it is a bop… moonlight (do me)…
  • Not being Andy.
  • Dylan and Hailey seem to be doing better whenever they’re not together, e.g. Dylan becoming a nurse and Haley starting a fashion blog.
  • They always make up and break up and it’s so inconsistent.


10. Aaron Samuels in Mean Girls

Image Credit: Paramount

It can’t be October 3rd forever, and eventually, we have to wake up and realize Aaron Samuels was not worth all the effort that went into getting him. He chooses Regina, and as a result, Cady tries to ruin Regina’s life. Like okay, where is the girl power? Kind of misogynistic of Cady, but whatever.

He is so bland. He is like plain butter. There are so many vibrant and funny female characters in this film and then he is just there. He is literally just Ken, and in the movie musical, he’ll even do the singing part of it all.

Let’s just say I’m not disappointed that Aaron didn’t make a comeback in the Mean Girls commercial.

Some of Aaron’s worst crimes:

  • Claiming to be such a good guy even though he doesn’t mind his girlfriend being horrible to people.
  • Dating his ex-girlfriend’s friend, like foul move, especially when your ex is THE Regina George.
  • Tutoring someone when he clearly didn’t have a good grasp of the subject matter himself. Is he too stupid to realize he’s stupid? Or is he too arrogant to think he’s good enough to tutor?
  • His LAME Halloween costume. A football player? At least dress up as Travis Kelce and have Regina be Taylor.
  • Not wearing his hair pushed back like that.

Let’s collectively write a fanfic where the three mean girls become a triad instead.

Fleurine Tideman
Fleurine Tideman
Fleurine Tideman, a European-based copywriter. She’s interesting (cause she’s from Europe), speaks multiple languages (again, she's from Europe), and is mentally unhinged (despite socialized healthcare). You can find her European musings on Twitter @ByFleurine and her blog, Symptoms of Living, both of which are written to the sounds of unhinged Taylor Swift playlists.