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Tuesday, Feb. 3, 2026
The Daily Pennsylvanian

Audrey Levenson | Your Halloween situationship got awkward. What now?

Ask Audrey | Let’s talk about your Halloweekend…

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Welcome back to “Ask Audrey,” my advice column where I do my best to answer your questions and weigh in with my advice. This week, we’ll be tackling the repercussions of one of the most drama-filled weekends of the semester: Halloween weekend, more commonly referred to as “Halloweekend.”

This week’s question: “I made bad decisions on Halloweekend and now I need to avoid this man’s advances. After certain things occurred between us, I would rather not continue our relationship (if you can even call it that). The issue is I keep seeing him everywhere and he keeps texting me. I want to let him down easy, but I don't want to make it too awkward because we have some mutual friends. Please help!”

Yikes! Thank you for writing in with this. One of the great joys of Penn is being able to stroll down Locust Walk and see all of the people you’ve ever met here. It’s the greatest tool this school has against the loneliness epidemic. But one of the great drawbacks of Penn is that it becomes extremely challenging to avoid someone when you’d most like to, particularly if you have mutual friends. 

I agree that you should try to avoid awkwardness as much as possible — you want to respect the fact that you had “certain things” occur between the two of you and that he may feel differently about it than you do. You also don’t want to create an uncomfortable situation for your mutual friends, who may feel weird about hearing the situation from both sides, particularly if you’re both complaining about the other person. 

I don’t know the extent of your previous relationship with this man, but I think if you’ve had any kind of previous interaction, you should have a conversation in person. When you have one of your unexpected run-ins, stop him and ask if he’s willing to chat for a bit sometime soon. Then, you can gently explain that you are not in a place to explore any kind of further relationship with him, but that you appreciate his interest. The best way to let someone down easy is to make them feel that nothing you’re feeling is because of any of their inherent flaws, and that you genuinely are flattered by the fact that they’re interested in you. 

If you’re not feeling particularly flattered, or if you genuinely are turned off by an inherent flaw, try to remember that putting yourself on the line for someone you’re interested in is a scary thing to do, no matter who you are. The fact that he keeps texting you does show a willingness to take a risk, which I think you can appreciate separately from anything you might not really care for about him. 

If I’ve completely misconstrued the situation and this is a man you barely know who doesn’t seem super invested in you outside of doing “certain things” again, then I think you can have a similar conversation, but over text. I know that might be controversial to some non-Generation Z readers, but if you guys haven’t interacted much in person in the past, doing this conversation face-to-face might actually make things more awkward for both of you. 

The last thing I’ll say on this is that if you decide you won’t let something get awkward, it won’t be. I firmly believe that awkwardness is a construct that you can take down with a simple mindset change, but as the person doing the letting down, you have to be the one to not allow the awkwardness to fester. If you see him in group settings after this conversation, be friendly and talk to him like you would to any other person there who you have mutual friends with. While this guy probably won’t be happy about this outcome, I’m fairly certain that you will be able to move forward from this and keep the peace among your social circles. Good luck!

SEE MORE FROM AUDREY LEVENSON:

Welcome to ‘Ask Audrey’

If you’re interested in submitting anonymously to “Ask Audrey,” feel free to do so here. All advice should be taken with a grain of salt. 

AUDREY LEVENSON is a College junior from Pelham, N.Y. studying political science and English. Her email is audklev@sas.upenn.edu.


SEE MORE FROM AUDREY LEVENSON:

Welcome to ‘Ask Audrey’