Secret Confessions & Open Frustrations of an Online Dater

Online dating is kind of like walking into a massive thrift store, overwhelming, unorganized, and mostly full of stuff that you really don’t want to take home. Trying to be open minded, you start swiping through what’s on the rack. What starts out as a slightly bemused expression on your face shifts to increasingly unimpressed disappointment. Yet, you have the sneaking suspicion that somewhere, hidden in the depths, is a gem that is perfect for you.


Am I speaking from experience? While more and more people are trying online dating, there is still a stigma, so we normally keep our online romantic pursuits a secret.  But, sheepishly and begrudgingly, I’m admitting to you, dear reader, that yes, I have been dipping my toes into this bizarre world these past few months. I thought, it being Valentine’s Day and all, that I’d share my mostly amusing, at times disparaging short lived adventures in this realm, for any of you who might be curious or just feeling their singleness more acutely on this particular day. And I feel the need to give the following disclaimer and hope that you believe me: Online dating wasn’t something I did out of desperation or neediness, but a choice I made, mostly out of curiosity and an attempt to lean into the story I find myself in. This is a personal and very vulnerable thing I’m sharing with you all, but I’m trusting there is camaraderie on the other end of the screen. I’m leaning into a transparency that I hope is refreshing and a reminder that we don’t have to take ourselves so seriously as we thought.

And so, in no particular order, here are some observations, discoveries, woes and amusements on the topic of online dating:

 1.  Oh questionnaire, you just get me!

As a writer, and an overly self-aware individual, the myriad of questions and steps involved in filling out my profile felt like a fun challenge. How could I most succinctly and eloquently sum up who I am, what I like, where I’m headed? Many others dread this part, but I actually loved it. (Says the girl who geeks out over personality profile quizzes and loves coming up with metaphors for where I’m at in life. Feel free to roll your eyes at this.) I felt hopeful filling this out, feeling giddy at the opportunity to articulate who I am in a platform that was going to be presented to all of these potential pursuers.

2.  The agonizing weight of a picture being worth a thousand words.

The profile creating also was extremely challenging and a process wrought with self doubt. Which pictures do I choose? This is the first impression these men will have of me. How will I be seen? Do I look braggy or cliche if I add too many pictures of my travels? What’s the line between choosing a flattering picture and looking like I’m trying too hard? Should I make it clear that I’m tall, so that men know what they’re getting into? Wait—I need a tagline? What the heck is that? Should I be clever? Ask a good question? Geesh.   

3.  I feel like I am essentially online shopping… for a human being.

Once I got my profile set up, then came the searching. It was a bit unsettling how similar it felt to shopping on Just like shoe shopping, I could refine my search by narrowing which hair color, height, education level, interests, or other features I was interested in. It was both really entertaining and also conflicting feeling like a customer in a consumer market. Yikes, I don’t know how I feel about how easy it is to approve or disapprove, swipe left or right, make snap judgements on humans. Although I guess we do that in real life all the time, whether or not we like to admit it. What exactly am I doing here? And am I ok with it? An equally sobering thought was the reality that hundreds of men were doing the exact same thing as I was, only with me. Swiping past my profile, evaluating the positives and negatives, making value judgements on a human with a story, with hopes and desires, a life.

4.  Really?? You thought that was going to attract women?

Moral dilemmas aside, I tried to encounter people, as they were, through this medium. To be open to possibilities and strike up conversations as they came. So as profiles of men came up on my feed as potential matches, it became quickly apparent that not everyone took the same level of intention or had the struggle of self-consciousness that I did with their profiles. I mean, the amount of selfies I’ve seen in the last two months has been enough to last me a lifetime: the bathroom selfie, the car selfie, the I’m-proud-of-my-beard selfie, the bar selfie, the hey-look-I’m-good-with-kids-but-don’t-worry-he’s-my-nephew selfie… I could go on. I’ve learned a lot about my preferences in the last few months, paying attention to my gut reactions. I’ve discovered unexpected deal breakers, such as not being drawn to people whose main passion in life is “Netflix and Chillin’” and not being attracted to people who claim to “live at they gym,” as evidenced by their flexed-muscle gym selfies. I found that it really made me cringe when men would make grammatical errors or completely forego punctuation. or just decide not to capitalize. (If I expect my third graders to write better than what I’m seeing on your profile, that shows either a lack of intelligence or a lack of general effort.) If you answer the question “What was the last book you read?” with something along the lines of not really being into reading, I’m moving on, buddy. Sorry.

5.  The Subtle Settling

You know that moment when you’ve been shopping for a little too long and you’re getting antsy to leave, but you still haven’t found what you’re looking for? (We’re jumping back into the thrift store metaphor…) Your eyes glaze over, and you start to think to yourself “Well, this shirt isn’t so bad. Maybe I like this?” The thing is, you can’t even tell any more. You wonder if you were expecting too much in the first place. I found myself trying to convince myself to be more “open-minded.” I found myself in this tension between knowing and trusting my gut, knowing what I want, and trying to be open, willing to be surprised. It was good to practice being open, although my gut won out every time.

6.  The Weird Culture of Flirting

There were a few guys that were interesting, seemed intelligent, and attractive. So then what? There’s this whole other world and way of interacting with people on these apps and websites. Is winking a thing? Should I message them? There was this weird pressure to be clever and charming, and yet at the same time, because it wasn’t in real time, there was all this time to (over)think about it, which was stressful!

7.  First Dates Are (Usually) the Worst

A few of these interactions led to a date. It was bizarre—feeling like I already knew this stranger. Will whatever possibility of connection we were feeling online translate in person? The drive to the date is always a brainstorm session of conversation topics so as to avoid the dreaded awkward silence, a pep talk of courage and deep breaths. The debate on whether or not to hug upon meeting? Wondering if I should try to reach for the check like Ted Mosby would want me to, or not. The key, I’ve found, is to not overthink it. Everyone is awkward on first dates, and if you just choose to make room for the awkwardness at the table, it’s not so bad.

8.  Trying to Not Become an Angry Feminist

The thing is, though, that awkwardness aside, none of these dates that I went on were that great. They were kind, they were gentlemen, nothing against them, but I just didn’t feel a connection. Which on one hand is completely fine, but what I noticed after awhile is that I started having these disparaging thoughts towards men in general. After one particularly lackluster date, I shouted “I’m just so sick of boring men!” in my car on the way home. Now listen, I do think that there are incredible men out there, with interesting lives, passionate and kindhearted, intelligent and worth knowing. I just don’t know where they are. I would love to be proved wrong, but in my experience, they are few and far between in the online dating world. And I realized I’d much rather just be single than try to convince myself to be with someone who doesn’t fascinate me, challenge me, or inspire me.

9.  It Isn’t Magic, it’s Just Exposure

A little over a year ago I went to this NPR Event, a storytelling night at this bar that themed around “The Science of Online Dating.” (Ironically, my roommate met her now fiancee there!) I thought I would go to that and be convinced that I should try online dating. There were many hilarious horror stories from other people who’d tried it, and ultimately, I remember the takeaway being that online dating isn’t this magic formula of how to find “the one,” but it is successful in that it ups your odds of meeting people, just through the simple act of exposure. It seems to me that you can’t create a reproducible way to meet someone and get married. Everyone’s story is different. In the advice that I sought out with the dating, they said the people who put the effort into it are the ones most likely to find someone. That being said, I did give that a try for a few months. It almost felt like a part time job. It does seem very possible to me for someone to meet someone and enter into a relationship. In a lot of ways, it’s not that much different than meeting people in real life, it’s just amplified.

10.  This Isn’t the Story I Wanted

I was hesitant for so long to try online dating. Mostly, I just didn’t want that to be my story of how I met my husband. To be completely honest, I’m not living the narrative that I thought I’d find myself in. If I had been asked to write my life story 10 years ago, it would have been very different the reality I find myself in right now, but you know what? It would have been a lot more boring, predictable, safe. The story I find myself in now is much more adventurous, vibrant, and beautiful than what I thought I wanted. If nothing else comes of it, getting an account on one of these sites was a way to enter into my story—both letting go of the what I expected and naming what I desire. Wrestling with what it looks like to both hope and be content at the same time. The truth is, I do feel a longing to share life deeply with someone, I feel ready to embrace that season in all that it means, and hey, if that means going through this roller coaster of a ride with attempting to date online, then so be it. And having found that ride to be exhausting and not especially helpful right now, I’m giving myself permission to get off. To leave the thrift store with empty hands and a smile on my face.

One thought on “Secret Confessions & Open Frustrations of an Online Dater

  1. Great post! I think you nailed it on many different levels. The online dating experience becomes exhausting after awhile, especially the repetition of it all.
    “If nothing else comes of it, getting an account on one of these sites was a way to enter into my story—both letting go of the what I expected and naming what I desire.”
    Beautifully stated!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s