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Confessions of a Hesitator: Navigating Digital Dating Anxiety

  • Writer: Anna Redd
    Anna Redd
  • Feb 20
  • 3 min read

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I’m a “Hesitator” when it comes to dating. According to How Not to Die Alone, there tend to be three dating tendencies: Romanticizers, Maximizers, and Hesitators. Hesitators have the tendency to find reasons that they aren’t ready to date:


“I need better photos.”

“I need to get my job in order.”

“Maybe after I lose some weight.”


Hesitators believe that aspects of their life or themselves are preventing them from taking that initial step to start dating. I felt “called out” while reading How Not to Die Alone’s chapter for Hesitators. I am ready to start dating, and there are no real reasons that I couldn’t start putting myself out there, but I tend to think of all the caveats and remain where I am.

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The Struggles of a Hesitator

I’m not a big fan of dating apps to start with—I just don’t think it’s the best avenue to survey people you like, and it creates a hub for superficiality and judgment. I also am not sure where I’ll end up after college, so I’m hesitant to start dating someone in Toledo and then move to Columbus in three months and have to do long distance.




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Aside from this, I relate a lot to How Not to Die Alone’s point that fear of rejection and failure contribute to being a Hesitator. It’s hard to admit, but this is a big reason why I don’t put myself out there. I don’t have a lot of experience with rejection or failure in dating, and it can be scary to navigate and communicate through that. I also fear that, at this point, the opportunity cost of my not putting myself out there has grown too high, and I worry I don’t have enough experience to navigate dating at all. All of that, plus my struggles with social anxiety, adds up to me being one BIG Hesitator.


Taking Steps Forward

I found the book’s suggestions to “just do it” not necessarily helpful, but some of the tips about taking action can be. The author talks about the “intention gap” that we get stuck in—where we intend to do something but don’t take the steps to make it happen. Hesitators get too hung up on the details and tend not to act, so the chapter suggested taking smaller steps, such as creating a dating app profile and preparing yourself mentally to start dating.

Some useful tips included:


  • Giving yourself a deadline to start putting yourself out there.

  • Referring to yourself as a “dater” to mentally shift your perspective.

  • Reminding yourself that neither you nor anyone you’re going to date is “perfect”—you don’t need to be a certain way to be able to start dating.


The sentiment of “well, just start” can feel incredibly daunting, so I say take the time you need and take those steps as you can. Reading these chapters in How Not to Die Alone really showed me that everyone has struggles and personal hang-ups when it comes to dating. It reminds me that “pobody’s nerfect” and that embracing those flaws and fears may actually allow us to connect more.


The Digital Dating Dilemma

Even beyond personal struggles, external issues in the digital dating world create tension. In Chapter 7 of Social Media and Close Relationships, the author refers to ludics and storgics in dating.


  • Ludics “treat love as a game to be played, avoid commitment, and enjoy juggling multiple partners.”

  • Storgics “perceive love as a deep, deep friendship in which sex comes later in the relationship.”


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I feel as if many people on dating apps are ludic. We’ve heard of the infamous “swiping game” that people may play with friends as harmless fun, but this just perpetuates the idea of commodifying people on those apps. It can be discouraging for people like me, who are actively trying to push themselves out of their comfort zones and find a lasting relationship. It can sometimes seem like nobody else is looking for that.


Additionally, the chapter covers cheating and its prevalence in the digital dating age. The author cites that “66 to 73% of college students reported they had at least one back-burner relationship.” Back burners are the people we communicate with in the event that we may pursue them later. Even those in committed relationships may have back burners, which can sometimes lead to cheating. Single people have back burners too—though I believe our generation calls our “little black book” a “roster,” and instead of a physical book, it may be a list of names in the Notes app on our phones.


It’s interesting to see how digital culture has changed dating dynamics. I feel like there needs to be a specific app for deep romantics, committers, and storgics like me. Until then, I’ll keep working on getting out of my own way and taking those first steps—one hesitant but hopeful move at a time.

 
 
 

2 Comments


Sofia Szymanski
Sofia Szymanski
Feb 22

Hi Anna! I agreed with so much of what you wrote about. I'm a hesitater too, and man is it scary to put yourself out there! I'm also afraid of being rejected in a relationship and I worry I'm not good enough for a partner. Some of this comes from self-image but a big part is because of how inexperienced I feel dating, like you mentioned. Being worried about dating all this time has only made me worry more because I feel so far behind. It's a struggle, and I understand why you said the advice given in the chapter was not necessarily helpful. Most of it wasn't for me either, but I did like the reminder to be more…

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adelle webster
adelle webster
Feb 21

Hi Anna! I think you really captured what (I would assume) it feels like to be a hesitator in relationships. Hesitator was my second highest score in the tendency quiz, so I relate to a lot of what you mentioned. Rejection is SCARY and sometimes admitting that it's as scary as it is can feel embarrassing, I appreciate your honesty and again, really relate to it. I noticed that being told to "just do it" was also tough advice to working on my tendency. As a Romanticizer, Ury told me to just shift my mindset, but how in the world do I just change the way I have been thinking my whole life?? So I'm sure just having to throw…

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