The Ugly Side Of Dating Taylor Swift

Taylor Swift and dating have become the Hollywood equivalent of oil and water. They just don't mix, no matter how hard she's tries. Why can't the songstress make love work, despite writing about it so many times? Well, like all of her relationships, it's a little complicated.

There's nothing wrong with dating around. If we were as rich and beautiful and famous and Swift, you'd best believe we'd be doing the exact same thing. The problem with Swift is that her taste appears to be all over the place. Past flames include X-Men star Lucas Till, Twilight werewolf Taylor Lautner, pop star Joe Jonas, socialite Conor Kennedy, musician John Mayer, Oscar-nominated actor Jake Gyllenhaal, Harry Styles of One Direction, Scottish DJ Calvin Harris, and now, Avengers villain Tom Hiddleston.

Swift has tried on a lot of suitors, to the point where she's giving off the impression that she has no idea what she actually wants in a man. Yes, that's normal for any 26-year-old, but when you jump from a scrappy DJ to a highfalutin thespian within weeks, you're telling the world you'll court just about anyone until you find your Prince Charming. In which case, it's no wonder Swift has kissed so many frogs.

Swift's relationships tend to be as brief as they are high-profile. One day, she's going to the zoo with the love of her life, and the next day, she's battling break-up stories in the tabloids. When she celebrated her one-year anniversary with Harris in March 2016, followers viewed it as a miracle, like the time Andy Murray became the first Brit in a bazillion years to win Wimbledon. We never thought we'd see the day.

That's never a good reputation to have when you're dating, even if breakups occur for reasons beyond your control. If your romances can't seem to make it past the three-month mark, nobody's going to take your love life seriously. In fact, we're willing to guess that people are already placing bets on when Swift's relationship with Hiddleston will come to an end. (Our guess? Next month.)

At this point, hearing about Swift's love life has the same effect as hearing a story your dad tells you on the way to the airport—you just want to roll your eyes.

Whenever Swift releases a single, listeners immediately wonder: which ex-boyfriend is she writing about? Swift tends to play coy on the subject of her muses, but fans have pieced the clues together over the years. For example, Swifties say "We Are Never, Ever Getting Back Together" was probably written about Gyllenhaal and "Style" was supposedly all about Styles. Swift has written about so many exes that every time she breaks up with one, the joke becomes, "Well, we look forward to hearing the song she writes about him." (We're looking at you, Harris.)

With that said, why would any guy in their right mind want to put themselves at risk of landing in one of Swift's breakup hits? It's like spending the night at the house in Who's Afraid of Virginia Woolf?—you just don't do that unless you're looking for trouble. We can only imagine how many guys have flat-out avoided Swift for that very reason. Until her music stops sounding like a teenage diary, it's hard to imagine her maintaining a grown-up relationship.

Beyond her romantic relationships, Swift has developed a habit in recent years of calling people out for their alleged mistakes. In fact, it's gotten to the point where she seems to be operating under the mindset of, "Fool me once, and I'm gonna tear you apart in public."

Obviously, there's the whole Kanye West fiasco, which in recent weeks has turned into a disastrous case of he-said, she-said, but Swift has also gone after well-loved celebrities, including comedians Tina Fey and Amy Poehler. She got mad at them for making fun of—you guessed it—her dating life at the 2013 Golden Globes. Swift told Vanity Fair, "You know, Katie Couric is one of my favorite people, because she said to me she had heard a quote that she loved that said, 'There's a special place in hell for women who don't help other women.'" (FYI, Taytay: U.S. diplomat Madeleine Albright said that.) Going after two renowned comedians for making a joke that everyone else has already made? Come on. If you can't laugh at that, you're probably taking yourself too seriously, and that's kryptonite in the dating world.

Arguably the craziest part of her newfound relationship with Hiddleston is how quickly it happened. Last time we checked, she was only weeks into her breakup from Harris, and now she's making out in public with a new flame.

If The Devil Wears Prada taught us anything, it's that nobody should move at a glacial pace, but jumping brashly into a new romance while the media is still covering your last breakup is a tell-tale sign that you're dating recklessly. Seriously, if you can't take time to reflect on your last relationship, how are you going to learn from your mistakes and make wiser choices in the future?

This one isn't really Swift's problem, per se. Sadly, we live in a world where men can be really insecure and intimidated by a woman's accomplishments, and Swift is the very definition of success. Between all the Grammys she's won and her net worth of some $250 million and counting, she could retire to a deserted island tomorrow and be rich and famous for the rest of her life.

But for now, she's smack dab in the center of the spotlight, and that can be a very intense experience for someone who's not into that level of scrutiny. Her relationship with Harris reportedly ended, in part, because he just wanted to do his DJ thing and skip all of those red carpets. At this point, if Swift wants a relationship to work, she's either going to need to find a guy who is equally accustomed to the fame and doesn't mind it or someone who has mastered how to rise above Hollywood and all its nonsense. (Think Amal Clooney.) Otherwise, she's doomed to repeat these same dating patterns.

If you're going to date the "Shake It Off" singer, you're going to have to contend with her large group of high-profile friends—aka the "squad." That can be a challenge for any guy, no matter how nice, or cute, or successful he may be. If you're dating Swift, you're sort of dating the entire squad. Say one wrong thing to, let's say, Selena Gomez, and suddenly you've got the "Bad Blood" music video all over again.

Like everyone else, Swift is eventually going to have to decide if she wants to make her girlfriends or her boyfriend a priority. In her twenties, Regina George-ing your way through a "squad" is just fine, but if Swift is still inviting her besties to the Grammys by age 35, let's just say, we'll probably be writing about it.