What I’ve Learned From My Failed Attempts at Online Dating

For every single person who needed to read this today.

I tried. I swear I did. I put aside my skepticism that true love can be sourced from dating apps. I chose to dismiss my past experience in light of the lessons I’ve learned since my last attempt. I decided to be positive, hopeful, and relaxed on my foray into online dating apps.

I did all the recommended things. I posted recent photos without filters. I was honest and clear about who I am and what I’m looking for. I stamped it with my own brand of charm and humor and sent it out into the Universe. Then, I reviewed the matches the algorithm attempted to send my way.

I’m not into fishing. Casual misogyny was a hard no for me. Blatant insecurities were a turn-off. Every now and then, I would stumble on someone who seemed kind. At least, red flags weren’t being thrown up in every direction on the profile. So, I would connect and try to carry on an authentic conversation with a total stranger. There were a few times I was even asked out — right before being ghosted.

Once, I even got my hopes up. Just a tad. They lifted off the ground for a moment. Nice person, with no obvious red flags, is seemingly single, plus common interests. A phone call confirmed our ability to converse. A date was set. I allowed myself to believe that there was a possibility. And then the text message came in. Something came up.

Of course, someone did.

To be completely transparent here, I rarely get my hopes up. My hopes don’t do that. They know better by now. Even before my last relationship when I had the biggest crush on that person, I did not allow my hopes to rise off the ground until his returned feelings were made clear. In fact, he later told me that I was hard to read and sometimes sent mixed signals. I don’t mean to.

I’m an open book — once I feel safe enough to be open. But I do keep my cards close to my chest. I’ve learned the hard way what it is to hope and be disappointed. I don’t prefer it.

What I’ve Learned from My Failed Attempts at Online Dating

My failed attempts at online dating became a pattern. I would start hopeful and try to connect. I managed my expectations. I went into it with kindness. And I always, always, always end up deleting my profile and then the dating app. But I learned a few things along the way that might be beneficial to others.

1. It’s Important to Do a Vibe Check of Our Profiles

After my divorce, my dating profiles were problematic. In fact, they got worse as my experiences did. Now that I’m healthier, I can see where I projected all the wrong things because I was still hurt and healing. I couldn’t see my own red flags, but I guarantee that healthy people did.

It’s important to vibe-check our own profile. Or get a friend to do it. Ugly comments about exes or generalizations about dating do not pass the vibe check. A list of physical requirements will be looked at askance. Lack of self-awareness isn’t cute, and insecurity is glaring on the apps. If we want to connect with healthy people, we need to become healthy people. Otherwise, we’ll continue attracting lessons instead of love.

2. It’s Important to Be Honest About How We Look

This year has been rough. I lost my job due to discrimination against my chronic illness. With that job loss, I experienced massive financial hardship. It’s been a challenging year all around, but I’m working through it, and my illness is at least managed with medication now. I say all of this to say that I’ve put on some weight that I’m not happy about. I’m uncomfortable with it. But it doesn’t change what is.

When I post photos, I post recent ones. I might not be at my ideal size, but I still love myself and want to present myself accurately.

As much as men complain on dating apps about women using filtered photos, men do it, too. In fact, I see it almost every single day when I’m on apps. It’s either that or pictures so old I can tell they were either taken with an old phone or an older digital camera. They aren’t as bad as developed films from the early 90s, but they aren’t clear, crisp, recent images either.

We all have insecurities. I know I’ll manage my stress and get back on a more consistent fitness schedule. I’m health-conscious, and I’m not worried that I’ll continue to put on weight. But I present myself as I am now, not as I’d like to be one day, and I appreciate it when others do the same. It’s one thing to try to show our best side and emphasize our best features. It’s another thing entirely to be intentionally deceptive.

3. Personalities Don’t Always Translate Well Online

I’m a big fan of establishing a few facts and then actually meeting in person. Some of us don’t translate well online. I know that I’m kind, smart, and funny, but sometimes, conversations are stilted because I’m trying to talk with a stranger who might not be helping the flow of the dialogue. It’s awkward, and it might be less so if more people were inclined (a) to be real and (b) to plan a meeting upfront.

I try to give people the benefit of the doubt. Some people have great personalities but might not be great at texting. Is the effort there? Do they seem like they’re trying? Am I trying, too? Those are the questions I ask before I move on. But I feel like the moment I’m not single-handedly bringing all the entertainment and zest to the conversation, the other person ghosts. And who has time amid the horrors to be a one-person song and dance number?

4. Personality > Attraction

I believe in the importance of being attracted to potential partners, but attractive people are a dime a dozen. They’re everywhere. In the end, it’s the personality that matters most. I’ve met visually attractive people with unattractive personalities, and personality will automatically cancel out any and all physical attraction. It’s not shallow to want to be attracted to people we date unless those people have a terrible character that we’re ignoring in order to continue to date them.

5. Compatibility > Everything

Character assassination is the go-to reaction to rejection these days, but compatibility is essential. We can choose to take it personally and get mad about it, but if someone says they aren’t for us, we should accept that. Some people just aren’t going to be compatible with us — even if it seems like they would be on paper.

That’s why dating is important. It allows us to get to know one another to see if we’re a good match. Sometimes, we find out that we’re not.

Sometimes, it takes a while for us to figure that out. Other times, we know right off the bat that something just isn’t aligning for us. Instead of taking it personally and assuming something bad about the other person or about us, we can accept that we’re not meant for everyone, and everyone isn’t meant for us.

Attraction is important, but compatibility is necessary for the health and longevity of a relationship. We might want to jump in and update our relationship status with someone we’ve got chemistry with, but it pays to evaluate compatibility before we take that leap.

I’ve learned that some people might seem like a perfect match, but if they aren’t feeling it, it’s not perfect at all. It might be disappointing, but it’s far better to see that reality than assume the other person is in the wrong for having different feelings about it.

The Truth About Online Dating

Of course, take everything I say with a grain of salt and a shot of tequila — figuratively speaking. I say that I’ve failed at my attempts at online dating, but a true failure would mean not trying at all. I have tried. I’ve gone in with a good attitude and returned disappointed.

I’m not making generalizations about people here, but I’m also not finding online dating or dating apps to be a productive use of my time. Especially when they almost never lead to in-person dates or even the slightest feeling of connection.

Online dating is hard. But let’s fix that: Dating is hard. It doesn’t have to be. More people could be honest and upfront about who they are and what they want. In an ideal world, we would all have had therapy and resolved feelings about past relationships. We’d click with the right people and part amicably with the wrong ones. But that’s not life.

People are messy. Feelings are complicated. But love — it’s worth it. I say that as a person who currently goes on no dates and has been single for what feels like forever. But I still believe. I still feel like there are possibilities out there in the world for me and love to coexist in a romantic relationship. I’m not making it something I live for, but I can honestly say it’s something I hope for.

Still, I don’t know that dating apps are the way to go — for me, at any rate. I gave it the old college try. I made every effort. Now, I’m choosing to take that effort and invest it into what I have, not what I don’t. But I’m learning. I learned a lot about myself from the many, many, many attempts at trying to connect. I learned what a good match feels like, and I learned to recognize when energies are out of alignment.

I became kinder than I once was and more willing to think the best of others even when presented with unhealthy (read: hurting, unhealed) energy. I’m not disappointed that I tried or that I learned from those experiences. I believe it’s made me better.

I accept that other people find online dating easier than I do. I know that there’s a world out there where people make dates and actually go on them — not ghosting or canceling at the last minute. Other people meet in real life and connect from there. Right now, I’m just sitting with the lessons.

I could go back to thinking I’m just a hopeless romantic stuck in the hell of hookup culture, or I could remember that timing is everything. This is my time to learn and to invest in myself. Maybe one day, I’ll get the meet-cute and connect with the right person, but I’m not holding my breath. In fact, I’m taking a full breath in and letting it out. Life goes on.

Somewhere out there, someone is catfishing someone else. At this moment, someone is being ghosted. A second ago and right now and in just another second, several people uploaded, are uploading and will upload an inadvisable picture holding a fish. And I am here — not feeling like I’m missing out on anything, just vibing and enjoying my life.