Problems You Had With Your Boyfriend In The '90s

When I think about my first forays into dating in the 90s, my first thought is “Thank everything that is holy and good that social media, dating apps, and sexting didn’t exist when I was in high school.” As a species, we tend to look back on the past as a more innocent time, regardless of when that past may have been. Usually, that’s just nostalgia talking and making us forget the complexities of life that make up any era, but when it comes to dating, I really do think that things were simpler twenty years ago. Those of us who liked boys may have had our own problems with boyfriends in the 90s (and I’m counting crushes here, too, because those are legitimate aspects of one’s romantic life), but those problems were more along the lines of “I am confused by the underlying meaning of his AOL screen name” than “Gee, I hope he doesn’t dump me by changing his Facebook status” or — ye gods — “I hope I can rely on him not to post private images of me on social media after we break up.”

Thinking about dating now vs. back then is making me nostalgic for those social-media-free days and for the boy problems many of us had back then. Everyone had their own attractions and turn offs in the 90s — after all, what looked like horrible, artificial, crunchy frosted tips to one person could look like heavenly hair gilding painted by angels to another — so the following list isn’t comprehensive. But if you were a person who was attracted to boys in the 90s (which not everybody was, of course), you may have encountered these problems with your BF:

1. He thought frosted tips might work for him.

(They really, really did not).

2. Fights via AIM.

In the early days of the Internet, we were all still figuring out how to communicate in a meaningful way via email and instant messaging (which, I know, seems incomprehensible now). So is it any wonder that a lot of online fights were caused by misinterpretations of tone and people not realizing when someone was being sarcastic? Helpers like “LOL” and primitive emoticons could only do so much to bridge the communication gap.


I was just at my in-laws’ house, and my husband and I spent some time sorting through his clothes from middle and high school. And they are all — ALL — a size XL or larger, at least double the size of the clothes he wears now, as a fully-grown man. When pressed for an explanation, all he could say was “I dunno, it was the ‘90s.”

So there we have it: The 90s, era of young men draping themselves in humongous Stussy t-shirts and Umbros, and feeling cool about it. Cher was right: "We're expected to swoon? I don't think so."

4. He was more into his Game Boy Color than you.

You were fun and all, but were you IN COLOR?

5. This ubiquitous haircut.

Floppy and parted down the center. Sexay, right? It would be inevitably followed by an ill-fated attempt at…

6. The Caesar Cut.

Buena Vista Pictures

I think George Clooney had some kind of magic in the 90s. Because I can’t think of a single other person who has made this haircut work, except maybe, you know, Caesar himself.

7. He tried to pull some of that Jordan Catalano bullsh*t.

A guy (or girl, for that matter) running hot and then cold isn’t strictly a ‘90s thing, of course, but those of us who grew up watching My So-Called Life knew to recognize this sketchy behavior as the stunt Jordan tried to pull on Angela when he made out with her, only to snub her at the Buffalo Tom concert. This’ll jog your memory:

Rayanne: “Would it kill you to… treat her halfway decent? Because, you know, she deserves it. And she’s not gonna wait around for you forever.” Preach, sister.

(Also, THAT SONG.)

8. CK1. A lot of it.

Everyone in the 90s — men and women — went crazy for Calvin Klein’s unisex fragrance, CK1, and all of the logo-ed apparel that went with it. The boys at school may have been a little too liberal in their applications of the scent (and, by that, I mean they were pouring it all over themselves). (See also: Drakkar Noir, Eternity, Polo Sport, Cool Water, and Acqua Di Gio).

9. He thought Aerosmith’s “I Don’t Want to Miss A Thing” was uber-romantic.

Lots of people did, probably. But that song — especially when played during formal dances in the high school cafeteria, as it always, ALWAYS was — made me cringe inside.

10. A Surge addiction.

Seriously, the amount of Surge your guy consumed could not have been healthy.

11. The puka shell necklace.

TBH, you thought it looked cool at the time. Now, you shudder.

12. Before cell phones: Trying to talk on the phone without pissing off your parents.

Finding time to discuss life’s mysteries with your one true love over the phone was hard when your parents were yelling at you to free up the phone line. And if you didn’t have a cordless phone, then you had to sit and talk right there in the kitchen. With everyone just milling around, listening in. The horror.

13. After cell phones: It’s still a mess.

By the late 90s, some teens were getting their hands on cell phones (and some of us were borrowing our parents'). While these early mobile phones solved some communication problems, they introduced others, like Bad reception and running out of minutes. (Somehow there were never, ever enough minutes).

14. Musical disagreements.

You and your boyfriend had a lot of music tastes in common: You could totally get behind Green Day, Beck, Weezer, Garbage, and lots of other bands. The rap rock stylings of Limp Bizkit, which he inexplicably adored? No, thank you.

15. He wasn’t Pacey.

PACEY. I feel like that's all that needs to be said.

16. He also wasn’t Heath Ledger.

I mean, a guy just couldn’t win.

(Also, sigh. So dreamy.)

Images: Sony Pictures Television; Giphy (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14); Buena Vista Pictures