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The Dartmouth
December 8, 2025 | Latest Issue
The Dartmouth

Freak of the Week: Back to the Future

Dartmouth’s premier relationship advice column.

Freak of the Week.png

I’ve been hooking up with someone repeatedly this term who I’ve hooked up with in the past. I enjoy hanging out casually, but I’m worried the other person is more invested than I am. I don’t see it going anywhere in the long run.  At what point should I stop seeing my former scheme?

- Running It Back 

In most situations, I’d tell you to prioritize your own wants and needs. But for this, the answer is clear: you should stop seeing them now. 

Imagine you’re in their shoes. You’re seeing someone you really like, maybe even hoping the relationship could go somewhere. Now imagine knowing the other person is not only already wondering not if, but when they should stop seeing you. They explicitly pose the question of “at what point” they should stop seeing their “scheme.” Not “if.” “At what point!” They already have one foot out the door. Isn’t that a little hurtful? I know it’s sophomore summer, but that doesn’t mean genuine feelings don’t exist. 

If you’re not getting emotional fulfillment out of this relationship and you don’t see it going anywhere, what is the point in spending time on it? You are wasting your time and your partner’s time. You are closing yourself off to better people and damning your partner to the same fate. 

I know that it’s tempting to keep a steady thing around. Easy, familiar, someone to hit a swimming hole with. But you are disrespecting yourself and your standards by staying with someone that you are minimally excited about. 

I know it feels a little harsh. But at a certain point, casual fun with a former fling has an expiration date. When feelings creep in, and they will, it turns into a heartbreak powder keg. The longer you wait to figure out when to end it, the more powder you’re packing in. Let them go and open yourself up to what you really want.

Tell them you’ve enjoyed the time you’ve had together, but you don’t see it going anywhere serious, and you think it’s best to part ways before feelings get any more tangled. Honesty is a gift. Sadness is a gift. It gives the other person the freedom to find someone who wants the same things they do. It also gives you the freedom to focus on what you actually want, whether that’s casual dating with new people or leaving space to meet someone you’re genuinely excited about.

So, YOLO, sure. Run it back if you really must. But think about it. You only live once. What’s the point of running it back with someone you’re not excited about? There are literally billions of people on the planet. Ok, at this school? Maybe, like, a hundred. But still! That’s 99 other options that might actually make your heart race. So make room. You’ll be glad you did.

- Leila

Happy summer! There’s a simple bottom line that guides the answer to this question: summer is generally when people are trying to “have fun.” Of course, what “fun” means varies from person to person. My guess is that if you’re single going into sophomore summer, you likely fall into one of a few different categories: 

1) You’ve been single for most or all of your time at Dartmouth and are used to hookup culture.

2) You’ve had multiple shorter relationships at Dartmouth. You’re a“serial monogamist.”

3) You just got out of a long-term relationship.

4) You haven’t explored the dating or romantic scene at Dartmouth much at all.

I’d venture to say that if you’re at all involved in the hookup or chronically-single scene at Dartmouth, you’ve probably gotten a sophomore summer memo from a friend or upperclassman that goes something like this: summer is a time of romantic exploration, which might mean casual fun with one or multiple people or even meeting a longer-term partner. Intentions are pretty fluid, but the default mindset is to keep things light while staying open to something more.

When it comes to the person that you’re seeing, it might be worth considering their romantic history on campus. Are they a serial monogamist who likes to get into relationships frequently? If so, talk to them and figure out if their intentions with you are different. Are they one of the chronically single types who never seems to be in a relationship? If so, I’d be willing to bet that they’re not really thinking that deeply about your relationship. 

Furthermore, evaluate their behavior towards you. Do they text or contact you frequently throughout the day? Do they ask to see or hang out with you outside of a hookup? These might be signs that they want something more. Finally, look back on their previous behavior towards you while you were hooking up. Did it seem like they wanted something more serious then? This also might be a good indicator.

Personally, I’d lean towards not saying anything — and definitely not ghosting them — unless the aforementioned signs are clear. I think that most people pick up on the casual vibes of summer. Things generally aren’t that deep. In terms of seeing other people, why not? Go for it. You aren’t exclusive with this person, and if you’re interested in others, it still seems worth it to pursue during this time of romantic exploration. Enjoy!

- Eli


Eli Moyse

Eli Moyse ’27 is an opinion editor and columnist for The Dartmouth. He studies government and creative writing. He publishes various personal work under a pen name on Substack (https://substack.com/@wesmercer), and you can find his other work in various publications.

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