ADVICE: Ask a Freshman Losing His Virginity

Monday, November 16, 2009
By Lee Kowalski
Syndicated Advice Columnist Lee Kowalski (SFS '13)

Syndicated Advice Columnist Lee Kowalski (SFS '13)

Dear Freshman Losing His Virginity,

I told one of my best friends that I had a crush on him when we were drunk on Saturday and now I really regret it! He’s been super awkward around me and when I text him to see if he wants to grab dinner at Leo’s he always has another excuse. Now I’m starting to worry that maybe I ruined our relationship even though I was secretly hoping he would confess that he had a crush on me too. What should I do to save this friendship?

– Admirer in Alumni Square





Dear Admirer,

Uh, hey, why don’t you take a seat? You want a drink or something? I, uh, wow my throat’s really dry. I’m just going to grab a sip of water. You sure you don’t want anything? You’re really pretty. I, uh, I’m just going to go grab a drink. Did I say that already? Hah, wow that’s so crazy. Wasn’t that party crazy? I had so much beer I’m like completely wasted. I’m seeing two of you. It’s like twins. Hah, I’m just kidding. You don’t have a twin do you? Wow, it’s really warm in here. Do you like Arcade Fire?





Dear Freshman Losing His Virginity,

My “Mathematics in Society” class had a take-home exam last week and the professor didn’t say whether or not we were allowed to collaborate so I assumed it was ok. A couple of us got together and worked on it and handed it in. Now I’m really worried that our answers are going to sound too similar. Is collaborating on a take-home violating the honor code? I don’t want to fail cause of something stupid like that. My parents will kill me.

– Honorable in Henle





Dear Honorable,

Oh boy, hah, this is so crazy. Hold on. Almost got it.  Oh shit. No, it’s fine, I’ve got another one. Oh look at that, it’s banana flavored. Hah, it smells like banana. Wanna lick it? Hah, I’m just kidding. That’s crazy. I, um, I’m just going to go the bathroom. I’ll be right back.

Oh fuck oh fuck oh fuck oh fuck oh fuck. How does this shit work? “Place applicator side flush with genitalia.”  Jesus, these two sides look exactly the same. Fuck. Uh, “squeeze midsection gently to seal reservoir tip.” What the fuck does that mean?!





Dear Freshman Losing His Virginity,

My roommate and I are not getting along at all. We chose each other through CHARMS, but she and I have COMPLETELY different hours. She said she was a late sleeper but every morning she’s up at 7am to go to the gym and her alarm wakes me up everyday. How can I let her know that she needs to be more respectful of my habits?

–Drowsy in Darnall





Dear Drowsy,

So which way do you want to face? I can do either. I mean, I’ve done both. In my head. Like I’ve practiced. And I’ve watched…educational videos. Yea, uh, cool. Heh. Uh. Heh. Like that? Oh wow, missionary. Kinky. Ok, ok, is it in? Is that it? Do you want lube? I have this bottle here. I, oh, ok, sure. OH MY GOD. OH WOW. I can totally see why people do this in movies all the time. This is great. Oh yeah, sure I can move. Hold on, let me get into a rhythm.

Relax, my roommate’s asleep.





Dear Freshman Losing His Virginity,

Help! My parents are cutting me off! They said if I don’t get my grades up they won’t pay tuition next semester. I’m trying really hard, but with so many extracurricular activities it’s hard to keep up with my work, plus I need to have some kind of social life. How can I balance my schedule? And do you know of any available jobs?

–Cut-off in Copley





Dear Cut-off,

Oooh. Oh my god. You’ve done this before. You’re so good at lying there. Oooh. Ow! Ouch. Can you just turn a little? Yeah, sorry, I’m not very flexible. Um, where should I put my hands? Do you… Ouch. Just…just like that. Yeah that’s AMAZING. Oh. Oh. Oh my god. Oh. Bagsfhinkslepsdlfkjsdf. Oh, wow. Phew. That was great. So, uh, what I do with this thing now? Do I just leave it on or…? Put it in the garbage? Really? Gross.