Before You Ask Me if I Have a Boyfriend in Boston, Read This Post.

I am not the smoothest when it comes to flirting with boys. When most people walk by boys they think are cute, they will usually smile or flip their hair or wink or something (my knowledge of interaction with the opposite sex comes solely from romantic comedies starring Freddie Prinze, Jr). When I walk past a cute boy, however, my gut reaction is to immediately look at the ground and walk by as quickly as possible, typically tripping over something in the process.

Found: Picture of me flirting in high school. Not Found: Boyfriend in high school.
Found: Picture of me flirting in high school.
Not Found: Boyfriend in high school.


If, God forbid, I somehow manage to engage in a one-on-one conversation with said boy, the results are both hilarious and depressing. Here are a few of my favorite incidents:

Jeff and the Jaws of Life

In high school, I had a huge crush on a boy I will call Jeff. Jeff and I shared fourth and sixth periods my junior year, both of which were incredibly magical for me. I had never actually spoken to Jeff before junior year (nor did I really speak to him much during the year either), but that didn’t stop me from pining after him. What few interactions he and I did have, our conversations typically went something like this:

Jeff: Do you have a piece of paper I could borrow?

Kate: (drooling, quickly rips out piece of paper from her notebook, but accidentally rips it in half) HERE!

Jeff: …thanks…

Since the school year was divided into six-week chunks, teachers typically moved our seats during each change. It was during one of these six-week change-ups that my sixth period teacher placed me in the seat directly next to Jeff. It was simultaneously the best and worst six weeks of my life. On the one hand, staring at him was much harder as I now had to rely on my peripheral vision, but on the other, this opened up avenues for me to speak with him EVERY SINGLE DAY. I would dream of conversation starters during lunch:


Kate: Nice weather today, don’t you think?

Jeff: Not as nice as your face.

Kate: Oh, please. Stop!

Jeff: Let’s be boyfriend and girlfriend.

Kate: OK.


Granted, conversations were more like:

Kate: (inaudibly whispering) Nice weather today…

Jeff: What?

Kate: (slightly louder whisper) Weather…nice…

Jeff: What?

Kate: (Shouting) LOOK AT THE WEATHER!

Jeff: …ok.


One day in particular, Jeff was feeling more talkative than usual. Toward the end of the class period, Jeff and I were working as a team to answer questions in the back of the text. We finished our set early, so Jeff started telling me about some story involving band class. More interested in his face than the story, I had no idea what he was talking about, but I mimicked his facial expressions to feign interest. If he was smiling, I would smile. If he would become serious, so would I. The story continued after class ended, so he continued telling it to me as we walked out the door. He must have hit the climax of the story, as he started to laugh louder than normal. Again, copying his form, I laughed too. In my head, the laugh was coy, almost a gentle giggle even. In reality, the laugh was more of a bleat, my mouth wide open with all teeth exposed. That’s when the line Jeff and I were following stopped moving, causing me to run directly into his back…and bite it.

I bit his back.

Here, again, is where my actions differ from those of other humans. Jeff did not notice that I had accidentally chomped at his backside. A normal human would have walked away and never said any words about it ever again, thanking God that Jeff did not feel my teeth sinking into his Northface.

Enter Kate.


Kate: I accidentally bit you!

Jeff: (not paying attention. Looking forward).

Kate: (attracts his attention by poking his shoulder until he turns around)

Jeff: What?

Kate: I accidentally bit you! (smiling real creepy-like)

Jeff: (turns around and walks away)


Jeff didn’t tell me stories anymore after class. He did, however, ask one of my best friends to prom. And she went.

Actual picture of me dancing near him at prom, where he took one of my best friends LOL.
Actual picture of me dancing near him at prom, where he took one of my best friends LOL.

Seducing Sam

Flash forward to sophomore year of college. I had a crush on a boy that was in my linked cohort class with me (which is basically a course where two subjects are combined into one). Our course combined American Political Thought and American Philosophy, literally the two most boring subjects of all time. While I stared at this boy almost as frequently as I stared at Jeff in high school, I had gotten a bit older and bolder. My sparked conversations would sometimes last almost a whole minute.

This boy, who I will refer to as Sam, and I had classes together in the past, so we were close enough acquaintances to be Facebook friends, but not close enough to hang out with each other outside of class. Should we see each other outside of class, my initial reaction would be to a) violently wave, then regret it and want to live in the sewers for the rest of my life, or b) literally turn around and walk in the other direction to avoid direct confrontation.

I happened to run into Sam on the way to my dorm one day, and I bravely chose option a. Catching up to him, I could see he was carrying the books from our course.


Kate: Hey Sam! What are you doing?

Sam: Oh, I just bought the books for our class. I seriously hate this class so much. I’m so mad I had to buy these stupid books.

Kate: (in an attempted sultry tone) Yeah…you should…burn them.

Sam: What?

Kate: (not dropping the tone) The books. You should burn them. You should burn the books.

Sam: (clearly ignoring my clever retort and after a beat) Have you done the paper yet?

Kate: No, have you?

Sam: No, I don’t know what I’m going to write about yet.

Kate: Ugh, totally. Me neither. (which was a lie because I had my topic and sources already planned)

Sam: Hey, text me when you have a topic so we can talk about it later.

Kate: (having never been in this situation before) Oh, ok. I don’t think I have your number.

Sam: Give me your phone and I’ll give it to you. (takes my phone and sexily enters his number) Text me yours!

Kate: (inaudible noises that sound like agreement)


Normal girls: Oh, a boy gave you his number! Text something cute and make him want to text you back immediately!


Kate’s brain: I have just the thing!


Kate’s text: Hey Sam—this is Kate. Burn the books!


As if my awfully unfunny joke hadn’t bombed the first and second times, I opted to text it to him one last time to instigate a response.


Sam never texted me back.


A more recent display of how my flirting skills have matured over the years (they haven’t) involves slapping a cute boy in the face after one of my friends told me the boy was gay (he wasn’t), but the wounds on that one are still pretty fresh so I’ll save it for another day.


I give you this post as a present as I have no doubt that as I find my place in Boston, a city that houses, I’m sure, millions of hotties, I will have numerous stories involving my lack-of-flirting skills.


3 thoughts on “Before You Ask Me if I Have a Boyfriend in Boston, Read This Post.

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