Caught in a Bad Romance

We were freshmen in high school. My over-eager boyfriend got me surprise gift after surprise gift throughout the day – each one cheesier than the next. A (singing) teddy bear, chocolates, balloons, roses, a card, a necklace, cookies…by the end of the day I was too skittish to even walk anywhere for fear of what might come next. I broke up with him the next day.

No love in this club

I took out a girl for V-day on maybe our third or fourth date. We went out to dinner then headed to Club Majestic (when it was a dance club). At the time, I was using my passport as a wallet, storing cash in it, because it was “slimming” in my jeans pocket rather than a bulky wallet.

We got to the club and the bouncer was stumped.

“What’s this”?

“It’s a passport.”

“Why don’t you have a drivers’ license”?

“I didn’t drive here.”

“I can’t accept this.”

“Why not? It’s a federal ID!”

“I need to see a drivers’ license.”

“I’m here to dance, not to drive!”

All arguments were futile, and we went to some other bar instead. There was no dancing

Love never tasted so good

I guess there had been red flags along the way to the climax of the horrendous date, and I had just been too infatuated to notice them. He played on the football team, drove a bitchin’ red convertible and went on all sorts of crazy drug and alcohol binges – you know, all the things that impress a (stupid) 17-year-old girl.
We had been talking at school, and I asked him to a movie. Reg flag #1: He asked to meet me there instead of picking me up. I justified this with “Gas is expensive, and it’s not a big deal. I asked him to the movie anyway.”

So the night of the movie comes. And red flag #2: He forgets. Oops. Picture a nervous girl in a Ramones t-shirt wearing the worst screemo emo make-up standing alone in front of your local movie theater doing every cliche nervous girl bit in the book- lip biting, hair twirling and an impulsive phone check here and there.

Then comes the grand finale. He finally arrives and doesn’t bother apologizing, but with his dreamy smile and soulful eyes I hardly notice. I buy a gargantuan 65 oz. cherry slushie, and he takes two cups for water.

“How sweet,” I think to myself. “He took a water cup for me! What. A. Gentleman.”

The previews for “Slum Dog Millionaire” start rolling, and I am already 75 percent done with my cherry slushie. To curb the sheer overwhelming fruit flavor, I reach for my water cup, only to find it filled with his old chew.

The subtle flavor palette that is cherry, tobacco and spit was completely lost on me, and I splattered the mush from my mouth to the floor.

I didn’t get a call back. Probably red flag #3.

Signed, Sealed, Delivered I’m Yours

A tradition at my middle school is to sell valentines to be delivered in class on Valentine’s Day. As I was buying some for my friends, my best friend dared me to send one to my crush.
Not wanting to back down from a dare, I agreed to, and in a moment of inflated courage decided to sign it too.

My crush happened to be in my class at the time the valentines were delivered. Out of the corner of my eye I watched him open it, turn pale and scream in horror. I started crying (thankfully silent tears) and didn’t talk to him again until high school. Seven years after the incident, I seduced him and promptly broke his heart. Revenge? It’s sweet.

That’s Amore

Last Valentine’s Day, I had a boyfriend of two and a half years. Despite the longevity of our relationship, things weren’t going that well. We were trying the long-distance thing while he was studying abroad, and it was definitely putting a strain on our relationship. 

Valentine’s Day was quickly approaching, and although things were a little shaky, I decided to send him a Valentine’s gift. As I was assembling his gift, I realized that I didn’t have a card or a Valentine to put in with it.
I quickly scribbled a hand-made card but was struggling to find things to put on it. 

Finally, I decided to draw a heart with our initials (cheesy, I know) to take up space. I debated whether I should put “Forever” on it. The fact that I questioned this should have been a sign, but I went for it anyway.

“Forever” ended up being the kiss of death to our relationship. We broke-up a week after Valentine’s Day. Unfortunately, the break-up happened before the gift made it to him. By the time he received his gift over a month later, we were long since broken up. Thank you Italian Customs!!

My Best Friend’s Guy

In the life of a 16-year-old girl, there are few single moments more monumental than when the boy you’re crushing on tells you he likes you back. When that beautiful moment happens to happen on Valentine’s Day, you feel like you’ll never forget it. Now I wish I could.

February of my junior year of high school, my best friend and I were into the same guy. We decided we would both go for it, and there would be no hard feelings no matter how it worked out. Maybe this arrangement would have worked if we didn’t have such similar backpacks.

After weeks of primping, Facebook stalking and lingering by his locker, I got my wish on Valentine’s Day. I found a small box of chocolates in my backpack as well as a card signed with his name. I was pretty sure that nothing more romantic had happened to anyone else in the history of time.

As every Cosmo article ever printed told me to do, I played it cool. For the next week, I upped the flirtation and time spent in his vicinity but made no clear reference to the confession of love left in my backpack. He did not respond. In fact, he seemed a little uncomfortable.

Not one to be deterred by small road blocks, I convinced my young heart that he was nervous I had not referenced the gifts. I started making subtle comments around him relating to hearts, chocolate and Valentine surprises. He only got more distant. I grew despondent.

When a friend threw a party the next weekend, I used it as an excuse to drink away a little of my heartbreak. After one (possibly many more than one) beers too many, he walked into the basement. Driven by my liquid courage, I charged right up to him and pulled him into a corner.

“Why have you been so awkward since Valentine’s Day”? I demanded. “Don’t you like me anymore”?

He looked around, more confused than ever. Possibly by my question, but also by my less-than-charming drunken demeanor.

“Well, your friend pretty much had you tell me she’s not interested,” he answered. “You’ve been making fun of that Valentine I left for her for days. So it’s a little weird being around you.”

After staring at him for a few seconds (probably longer), my slower-than-usual brain put it together. He had gotten our backpacks confused and thrown the chocolates in what he thought the bag of my best friend. I was the object of no one’s affections outside of my own fantasies.

I stumbled away and after a short internal debate told my friend. They started dating immediately, and I was left with only the knowledge that good things happen to good people to comfort me.

Karma got my back a year later, though. After the dust from their inevitable breakup had settled, we made out at a party.

Love is like a box of chocolates…

The year was 1999, and I was in fourth grade and in love. I had had a crush on Kyle S. for like, my. entire. life. This was the era when you had to give everyone in your grade a valentine, even the ugly kids whose lives you permanently scarred at recess. But Kyle was more special than that. At at time when desks opened up and had your name on them, obviously the only appropriate way for me to express my affection was to buy a small box of chocolates and slip them into his desk with a note.

My stomach had butterflies all morning, wondering when he would tell me he loved me back. Until I was putting on my jacket for first recess and found the chocolates had been stashed in my coat sleeve.

Most young girls would be devastated. Maybe even cry. But I was determined. He was going home with those chocolates if he loved me or not. Thus began the Valentine’s Day war of the unwanted chocolates.

I hid them in his boot. He put them in my desk. I gave them to his friend to give to him. My best friend gave them back to me. I stashed them in his lunchbox. They turned up in mine.

Finally, the last school bell rang. After an an emotional roller coaster day of anticipation, I ultimately discovered the chocolates wedged in a pouch of my backpack. As I stood in line for the bus, utterly defeated, another classmate turned around and asked me, “Hey, are you going to eat those”?

I looked at him. Back to the chocolates. Back to him. And promptly shoved the chocolates into my mouth. Victory.

Cupid (bitterly) strikes his arrow

So a friend of mine has a girlfriend who attends UW, and he asked me to do him a favor for Valentine’s Day. Since he goes to school in a different state and isn’t able to see her for this stupid holiday, he asked me to pick up some assorted chocolates to drop off at her place on his behalf. Easy enough.

I agreed to do it so I went to the candy store to pick out the chocolates. But for whatever reason, after a few minutes in the store, I realized I was getting really into it. I got these customized Bucky Badger chocolates and picked out some with the trademark Motion W. I spent way too much time thumbing through all the possible combinations until I finally had the perfect box of V-day chocolates.

Then reality set in. This was for my friend’s girlfriend. Why the hell did I care so much?

I crafted this awesome Valentine’s Day gift that was just going to get passed off so my friend would look good (and trust me, this gift kicks ass). So yeah, being single felt pretty depressing. It was hard to not get at least a little jealous.

But it was even harder to hold back from devouring that goddamn perfect box of chocolates.

Moves like The Situation

I spent my freshman year looking for someone since my high school girlfriend had dumped me and I was living a single, lonely life in Lakeshore. Unfortunately for me, one particularly unattainable girl kept teasing me with on again, off again signals, making me think a date would be a good idea every month-and-a-half but shutting me down before I had the chance to ask. Other smaller encounters with other girls just weren’t working, so I persisted with her.

As Valentine’s Day approached, I finally grew the balls to ask her to a short date on State Street. She insisted it be friendly and platonic, which I assumed would work out since it had taken me so long in the first place to react to any hints she made. By this time, I could only run on the “she’ll fall for me after she’s friends with me” strategy.

It was a disaster. No interesting conversation or moments. I would not even call it platonic since it made me like her less. I left Madison for Chicago that weekend to see my best friend, pissed about the encounter I had with her and ready to drink it away.

After acting like a true Badger in enemy territory, I ended up getting an invite to a girl’s dorm.

We sat down on her bed. There hadn’t been enough sexual conversation for us to start making out, and honestly she didn’t seem DTF at the time. So we talked a little about her life, She asked me what my life at UW was like and, naturally, I began telling her about my botched date. 

Every detail of my 3-month long escapade with the girl became a story that gradually decreased any chance I had of hooking up with her that night, and eventually she walked me back to my best friend’s dorm since I was too drunk to know where it was. I kissed her on the cheek as my friends walked in the door since I thought it was the gentlemanly thing to do.

The next morning I came back to Madison and after several hours of thinking I decided to send her a Facebook message apologizing for my drunken impotence and wishing her well in whatever she wanted to do with her life. My colleagues at the Herald asked me what had happened, and the only way I could describe my failure was to say, “I told her about my life!”

Two weeks later, I returned to visit again. My best friend still had her number on his phone since mine had been broken. She wanted to meet me again the next day. We hung out and made out, but not before she asked me if I had hooked up with the girl in Madison.

Now they’re both a distant part of my memory, only preserved in my memory and my Facebook friends list.

Roses are red, violets are blue, when thinking of love, I’m not thinking of you

Many of my initial lessons in love came in middle school.  Rotating “girlfriends” every other week can teach you a lot when you know absolutely nothing about the opposite sex.


One of the most important truisms I learned is now the most obvious. But I was young and reckless, and my hormones had my prefrontal cortex in a sleeper hold.


As it turns out, dumping a girl on Valentines Day doesn’t just make you an unforgiveable ass hole. It drastically decreases your future prospects for dating.


When everyone you know knows your girlfriend, word gets around that you dropped her like a beef pot roast at a vegan convention on what is supposed to be the most romantic night of the year. Having two of your best guy friends at the table when you do it doesn’t make it any better.


Luckily high school was just around the corner. Hello ladies.