Taylor Swift’s pandemic-era album Folklore spins several sonic tales of love and regret—but perhaps none tackles the wistful remembrance of a fleeting, but passionate, connection much like “Cardigan.” One lyric, in particular, captures why a short-term relationship breakup can sting so much, sometimes just as much as the end of an LTR: “I knew you’d linger like a tattoo kiss; I knew you’d haunt all of my what-ifs.” Indeed, the end of a brief romance can be even more painful than that of a longer-term one because it stirs thoughts and hopes about what could’ve been.


Because short-term relationships only last for, well, a little while (say, a few months), they typically don’t have time to become fully realized. Maybe it was a sexy vacation fling that ended when you both returned to your respective corners of the world or a summer of dating filled with sweep-you-off-your-feet romance. Maybe your memories are of a bond that broke because you were two ships passing in the night, and the timing was off; or of someone with whom you spent a whirlwind of late nights spilling all your darkest secrets until you just didn’t anymore.

It’s not uncommon to turn these relationships over in our minds and wonder what would’ve happened if they lasted longer, relationship experts say, especially if they didn’t end in a fiery blaze of hurt feelings or because of some specific reason. The key ingredient that can make the end of these memorable short relationships so painful is the hope of it all.

How hurt you feel at the end of a relationship—and how long that feeling stays with you—isn’t directly tethered to its length.

The idea that a short relationship can be just as painful (if not more so) as one with a longer shelf life cuts against general guidance about how long it typically takes to heal from a breakup. It makes sense that knowing someone longer generally means a deeper bond, and therefore more pain when that bond severs. But logic and feeling don’t always align, says Thriveworks therapist Victoria Riordan, LPCC-S. How hurt you feel at the end of a relationship—and how long that feeling stays with you—isn’t directly tethered to its length.

Why a short-term relationship breakup can hurt so much

Since short relationships often end in the honeymoon phase, therapist Melissa Divaris Thompson, LMFT, says you don’t have all the information about this person and their particular flaws and quirks to really form an opinion of whether they’d make a good long-term partner—so you fill in the blanks with your hopes for who they are. This lack of information can make it especially tough to reconcile a breakup after a shorter time together because it gets your mind turning with possibilities.

Thompson says she sees this dynamic often among her clients. “They start holding hopes and pinning dreams [on this relationship] in such a way that the fantasy is even better than the reality,” says Thompson. “When you’re with somebody long-term, you know their faults and can have a more grounded view versus when you first start dating somebody and you think they’re amazing partly because you just don’t know them that well.”

“It’s all about hopes because it’s that first rush of excitement, and reality hasn’t quite set in yet.” —Victoria Riordan, LPCC-S, therapist

Even if some more serious topics arise in conversation with this person, it’s possible to just red flags in the relationship because you’re so invested and swept up. “In the first couple months of a relationship, we tend to say, ‘That’s not important’ at any potential problem, [whereas] in longer relationships, we often have more conversations about struggles,” says Riordan. “It’s all about hopes because it’s that first rush of excitement, and reality hasn’t quite set in yet.”

You may find yourself jumping years into the future and imagining what life with this person could be like, and it can be really disappointing if it doesn’t go the way you want it to. “It’s a feeling that this could have been amazing for whatever reason, so then that opens the door for a lot of us to turn internally and be like, What could I have done differently?” says Riordan. It’s perfectly fine and normal to feel this way, but when these musings of love lost become sources of anguish or sadness, it’s good to rethink them.

How to handle the hurt from a short relationship ending

To deal with the feelings resulting from a short-term relationship breakup in a way that won’t spike your regrets, both Riordan and Thompson say it’s key to feel your feelings and acknowledge them. The issue with regret is that it can kick off a cycle of rumination and self-criticism that can impair your ability to live in the present.

One way to reframe that regret is to focus on appreciating the relationship for what it was. “We can say this was fun and I’m sorry that it’s over and feel sad, and then move on to our next moment instead of getting pulled down into regret,” says Riordan. Let’s say you’re in a vacation romance that ends in two weeks; reframing that time as a fun way to experience a new city with a knowledgable tour guide, or just as a great two-week bond, rather than your long lost love, could help take some of the sting away when you’re thinking about it back home.

Naturally, you can still miss this person and how they made you feel, but that mental shift can be a helpful check when you find yourself fantasizing about them and the relationship in a way that dips into regret. “If we expect every relationship to turn into the love of our life, we’re going to be disappointed, and when we easily get swept away by every relationship, that’s where we get discouraged and start to look at dating as exhausting instead of an adventure,” says Riordan.

Another way to help yourself not get bogged down imagining what could’ve been is to try to take things slowly as you get to know someone. As Thompson says, dating around and seeing people is part of finding whom you’d like to be with, so you’re bound to get into relationships that aren’t fully realized. Understanding that some of your relationships will end is all a part of that.

If you find yourself often dealing with the sting of a short relationship ending or ruminating on what could’ve been, Jess Carbino, PhD, relationship expert and former sociologist for the dating apps Tinder and Bumble, recommends “setting up some boundaries” to protect your heart. For example, spacing out your dates with someone new instead of scheduling multiple dates in a week could help provide some perspective, and having an open and honest conversation with whomever you’re seeing could help minimize the hurt should things end abruptly.

Being honest with yourself and others about what you’re looking for can also help you avoid getting swept away. Having a clear DTR (aka “define the relationship”) convo with any person whom you date for more than a few weeks can help set expectations for what you’re getting into (or not). “If a relationship is never defined, people have the capacity to believe that it could go in any direction, and ambiguity could lead to a great deal of fantasizing that could be problematic,” says Dr. Carbino.

With these tips, short relationships can turn into interesting stories, memories, and learning experiences—or fodder for song lyrics—instead of regrets that keep you up at night.




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Harmony Evans is an award-winning author of Harlequin Kimani Romance, African-American romance, and so on. Harmony Evans is an award-winning author for Harlequin Kimani Romance, the leading publisher of African-American romance. Her 2nd novel, STEALING KISSES, will be released in November 2013. Harmony is a single mom to a beautiful, too-smart-for-her-own-good daughter, who makes her grateful for life daily. Her hobbies include cooking, baking, knitting, reading, and of course, napping and also review some of the best-selling and popular brands and services in the market and also write comprehensive blogs.

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