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An underclassmen friend applied to one of my clubs and was rejected. I encouraged all the freshies I know to apply, including this person, and I know they were disappointed by the result. I feel like I’m partially responsible for making sure that they feel positively about Penn and find a place here. Now they want to talk about what “went wrong.” But after what happened, I’m not sure what to say or even if I should be the one to reach out.

Dear The Best Kind of Ship Is A (Dear) Leadership,

INTP: This is a tough situation that unfortunately (and perhaps unnecessarily — though that’s a different conversation) many upperclassmen experience at Penn with underclassmen that they have met and developed friendships with. I definitely think that it is important that someone reaches out to your friend, especially considering the many conversations surrounding rejection and mental health at Penn.

ESFJ: If I were in your shoes though, I would know what I would want to say, but I wouldn’t feel comfortable being the one to talk to them. Which is hard, especially if we’re close and if I’m usually able to be there for them. This situation feels like it gets in the way of a really meaningful mentor-mentee relationship.

INTP: It’s hard to actively take a step back, but I think your instincts are right-on. Another good friend, someone not in the club, should have the conversation on your behalf. You can brief them on the underclassman’s strengths, weaknesses and even offer some advice, but it should all come from the neutral third person.

ESFJ: As an aside, this is not the first time Penn as a community and the DP specifically have discussed club recruitment. Overly selective processes privilege extroverts like myself. And this situation doesn’t even come close to the potential awkwardness of getting into a club when your friends, roommates or colleagues don’t.

INTP: I think what’s ultimately most important though, is that your friend feels supported and understands that rejection in one situation might lead to a new and unexpected opportunity in another area, an area that might actually be a better fit. As a result, just demonstrating that you care, and making sure that someone reaches out about the rejection situation specifically, will really go a long way.

Awkwardly yours,

Over-committed & Empathetic

Two people (and past hookups!) are in the same organization and have a lot of mutual friends, which I discovered at a party when they were both there. Awkward. Plus, I proceeded to hook up with one of them… again. The other, still unaware of their counterpart/competition, is still hitting on me. How do I navigate this minefield?

Dear Threesome-in-the-Making,

Hot: Damn, damn and even hotter damn. Just have a threesome! (Just kidding… unless you’re not.) We can definitely see how this situation would present some challenging predicaments. I do feel, though, that college is the time to explore your sexuality: what you want, who you want, and this freedom is truly liberating. If everyone is operating without strings, so-to-speak, then enjoy the ride (literally and figuratively).

Bothered: But also be upfront about the situation. You don’t want to hurt people’s feelings, you don’t want to come off as insensitive, and while we’re no defenders of scarlet letters we also can’t pretend that people keep this kind of thing to themselves. You don’t want to be in a situation where you are perceived to be leading on either of your hookups. You also don’t want to be the accidental wedge that splits open their social glue.

Hot: One feature of this submission that catches our attention: By keeping the genders neutral, we’re not sure how to visualize our protagonist or their suitors. This is a good thing! Think: A man leading on two women might be a womanizer, hypersexed, in-it-to-win-it; a woman flirting with two men might be sex-positively-empowered but also flirting with an unfair, outdated label of promiscuity; a less heteronormative version upends these but also brings its own stigmas and stereotypes. Instead, we’ve had to put away our socialized gender and sexuality norms and approach this with as much level-headedness as possible, while also appreciating the Beautiful/Dynamic/Sensual/Matchless opportunity to explore sexuality with multiple partners.

Bothered: At the end of the day, do what makes you happy! The responsible thing is to think about what could go wrong before it does — to know what you’re getting yourself into, in spite of (because of!) being into it.

Awkwardly Yours,

Ready for Our Close-Up


Who are we? We’re like Batman and Robin, if they had to hold office hours at Saxby’s. We’re here to answer questions about your awkward situations at Penn — because chances are that we’ve been there, or somewhere pretty similar. “Wow, I just met my roommate’s Dad as I came home in last night’s clothes at 8 am!” Yes, that’s been us. There are moments that are humiliating, hilarious or genuinely uncomfortable. We’re here every week with advice, a touch of humor, and a healthy dose of affirmation to remind you that we’ve all had finest moments. Your no-judgment place to show your less-than-Penn-face. Submit your situation for advice here!

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