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Being a freshman is hitting me hard, but the hardest part is trying to hit on someone very much out of reach, a.k.a. the hall counselor. He’s an upperclassman. He knows so much, and all the boy freshmen I know admire him. He probably wouldn’t go for a freshman like me, but oh well. How do I approach him anyway?

~ Unrealistic Daydreamer


Saying age is but a number is difficult to do. However, since this is college, we are all within four years of one another…so, don’t let the fact that you are a freshman keep you from shooting your shot! Honestly, what is the worst thing that can happen? If you flirt, or, to the more extreme end, if you ask him out, the worst he can say is “no.” Although hearing “no” can be disheartening, it will allow you to move on. Since he is your hall counselor, he is older, and he seems to be an admirable person, so one would hope he could keep things unawkward. Also, these things are awkward for a week at most, but you have more important things to focus on, so eventually it’ll just be a funny story for the future.

The best way to approach someone is to ease into a conversation where you both feel comfortable. In other words, find something you have in common and talk about it. Most hall counselors have a little board outside their room where they have posted information about themselves, so find something there that you can comment on, study up, and see where things go from there. 

If you want to get more real and intense, you can think of (or even make up) a problem you have with your roommate or school, and ask for advice. Then, you can arrange future meetings to check on the “progress” of this issue, which will allow you to keep meeting with him as frequently as you want to, and it will also allow you to have complete control over the situation!

Another option is to take advantage of situations when you are together. This applies to hall meetings, or, if you all do hall activities, always try to participate in talks and be near him (but also stay six feet apart) during in-person ventures. The best way to get his attention is by giving him your attention. People enjoy being flattered, and people want others to want to be with them. If you give him flirty glances, laugh at his jokes, and, if you’re feeling brave, establish physical contact with a stroke on the arm or a shoulder bump (still six feet apart, mind you), he will most certainly notice you.

Relationships run their own course, and there is little that you can do to control that, but starting a relationship can most certainly be instigated. Don’t be afraid of what if’s and maybe’s and live in the moment with him. The most important thing to remember is yourself: is he worth potential awkwardness? Will he make you happy? If the answer is yes, then take this advice.

Always here to answer your pressing queries.

Best of luck, 

Told You So. 


I’m a senior and everyone who I could be romantically interested in feels too young for me. Is it okay to date a sophomore or freshman, or is it weird and cougar-y?

~ Unwilling Cougar 


Mmmmm yes. A question as old as time. First, I would start by asking you what is wrong with being cougar-y? Don’t we all hope to one day be a cougar? I personally can’t wait to one day live by the water and spend my days caring for my plants, doing the crossword, and prowling for sexy youths. 

I would suggest that before you make your move that you ask yourself a couple questions. What is attracting me to this younger hottie? Is it their youth? Am I missing my own younger days and wishing to possess theirs? Maybe you miss a time before COVID when there were actually people around and things to do other than eat, work, sleep, and watch the shadows grow longer, and you believe they might take your mind off of the monotony for at least a moment :/ Why ask these questions? Self-awareness. If you answer yes or no, it doesn’t matter, but I do think self awareness is key to owning your actions. Own the weird. 

There are a couple things you should keep in mind, however, before diving into this risque affair. Dating younger does come with its own unique set of complications. For example, they could start treating you like a parental figure and ask you to do their laundry. Soon you’ll find yourself setting alarms for them to make sure they get to class on time. If they start calling you “grandma,” then you know it’s time for things to come to a close. Also, they could expect you to have your life together when, of course, you do not. Even worse, you could start acting their age and find that you spend most of your day on the TikTok. 

I would like to end by saying that if you think that this freshie or sophomore will bring you some happiness, then please, go for it. We all deserve a little joy right now. The world needs a little more love out there, so please, get cougaring if that is what your heart desires. 

Always here to answer your pressing queries.

Best wishes, 

Told You So.