When Online Dating Goes Poorly

If you date long enough you are bound to have a succession of encounters that don’t go as planned. Romantic interests disappear, don’t show up, blow up over something small or just generally seem like train wrecks. Occasionally, when these occurrences stack up it can start to weigh on you. The question then becomes, what to think about these situations and how do you process what happened?

Trust me when I say that this happens to everyone. In fact, that’s what inspired this piece. I was watching my friends go through the same types of occurrences I was and it made me realize what a universal experience we were having. This was despite the fact that we were searching for vastly different types of people. Allow me to share a less than ideal week from my dating past so you can have a few examples. 

I met someone for a date that didn’t go well. Sadly, it was some of the most shallow conversations I have had on a date (I guess someone had to win that title). The one important thing we touched on was that the other people she had been out with didn’t feel as if she liked them so they quit asking her out. I also came to the conclusion that her repeated claims of independence served as a cover for her apathy and distance from others. However, since I generally give people the benefit of the doubt on first dates I decided to see her one more time. After all, maybe she was just nervous and we would have a better time the second go round. 

Despite saying she would like to go out again, she would take 24 hours to return each of my messages. This meant that every day our conversation would progress one additional text. This is far from ideal and doesn’t exactly scream “I’m interested” so I decided to make an inquiry. 

I asked if she had any interest in continuing our connection. I mentioned that the infrequent communication made me feel as if she wasn’t interested and I wanted to check in to see what she was thinking. I let her know that if she wasn’t interested in meeting up again that I would understand and there would be no hard feelings on my end. She replied quickly this time; I must be needy she said and she is no longer interested. I didn’t spend any effort trying to convince her otherwise. I thanked her for her time and wished her well. 

The second scenario involved a person who didn’t want to text except to set up a time and place of my choosing in which to meet. When I suggested we get together for a drink so we can get to know one another they ripped into me saying, “Would you approach someone you liked in public and ask to meet for a conversation?”

Since walking up to total strangers and asking for their hand in marriage has historically been fraught with problems for me, I tend to take a more cautious approach over a drink or dinner. Finding out who someone is and what they believe is important. It beats waking up one day after 20 years and saying wait, “you’re actually 30 years older than me, don’t speak any English and are running a fanzine for white supremacists?” Humph! Fool me once . . .

I tried to ascertain what this person meant as their text while full of emotion wasn’t exactly clear as to the meaning. They never messaged back. 

The final incident was with someone I enjoyed messaging. We were trading jokes and they had a sharp wit about them. Everything was going well and on day two when I went to ask them out they had removed our match and were gone. It felt unfortunate for me because I was looking forward to meeting. 

Situations such as these can be frustrating. It can be challenging to match with others and if those matches end up being the types of experiences I mentioned then it can be especially demoralizing.

So what was going on with these people and in similar situations how should you handle it? In truth, I don’t know what made them act as they did, and I don’t intend this to be dismissive, but I don’t need to know either. I also don’t think you should pay it any mind because if done properly you’re probably better off without their company. Here’s the first thing you should know. 

Be the best version of you

This is so vitally important. You should always be as kind, compassionate and understanding as you can. I’m operating under the premise that you want to be these things. If you’re one of those folks who wants to be a jerk all the time then be that, people will appreciate knowing to avoid you from the very start; just know the rest of this article is more about you than for you. So, if you aren’t rude, shallow, sexist, off putting, or exhibiting any other horrible traits then there’s a huge upside. 

You see, it’s worse to try and tailor yourself, however slight, to another person’s interests and then have things not work out. You will wonder “what if I was actually being true to who I am, would this still have happened?” If you’re honest and forthcoming and things go south there’s nothing to second guess. You were the good you and if they didn’t like that then it’s okay. After all, you want someone who will appreciate you for you. In situations like this, it was probably a simple mismatch in personality and not only is this common, but it’s nothing to worry about either. 

So once you’ve done some introspection and checked yourself then you’re good to implement these next ways of viewing your situation. 

It’s most likely not about you

I alluded to this above. Our personalities come out through any type of contact so you shouldn’t worry about a simple personality mismatch because statistically that’s going to happen most of the time. 

The other thing that happens is a lot of folks seem to get triggered nowadays and I think it’s partially because we have put dating at our fingertips. There’s nothing wrong with dating apps (in fact I think they’re great) but it does mean that more people are dating before they are ready. 

Think about the difference between dating now and 20 years ago. Back then, you had to tend to your appearance, go outside of your home, and work up the nerve to approach someone in person. This took a lot more resolve than it does now. Today you can put yourself online while laying in bed wearing your favorite crossdressing outfit (Ah come on, I know it isn’t just me). So it makes perfect sense that once folks begin messaging on dating sites/apps that they might decide they aren’t quite ready to be out there just yet. That’s perfectly understandable. 

The other thing is that it’s hard to know what’s going on in someone’s life. Everyone has their own demons and triggers and it’s not your responsibility to be accountable for them. I know that sounds harsh so allow me to expand upon that idea. Just like before, I’m not saying you can be a jerk but if you unknowingly hit on something that is upsetting someone then you aren’t to blame. 

You may text someone about a dog laying at your feet and make them realize they are too heartbroken over recently losing their pet and they aren’t in a position to be open to someone else yet. They may never respond to you again after this realization and that is their choice but it’s not your responsibility that a regular conversation triggered them. 

That was a fairy innocuous example (one which actually happened to me) but the point is, maybe they have had a horrible day, have commitment issues, an abusive relationship in their past, or any number of things. There is certainly a reason but you’ll likely never know what it is. It would be great if everyone who was triggered could have a discussion when it happens. That’s not how being triggered usually works; people tend to retreat, not open up. 

Just operate in good faith and don’t let it get under your skin. 

Assume the best and keep on rolling

I can hear you saying, “why do I assume the best?” It’s a good question and the answer is simple. You have two ways of thinking about this. You can internalize it and make it about you. This is a mindset that will eventually bring you down wondering if you’re good enough. This way of thinking can eventually become a form of self harm. Or you can say, “they must have had something going on in their life for them to act like that, I hope they find what they want.” This approach is a forgiving way to view someone who may be having a difficult time and it leaves you relatively unencumbered to venture on to someone else. 

Also keep in mind that if you date long enough then you will eventually become someone else’s mystery. Think of a time when you messed up by being triggered, didn’t text or call someone, or otherwise just dropped the ball. It’s alright. It happens, but you probably wanted the benefit of doubt in those situations so extend a few good vibes their way as well.

Ultimately, it is on them

Whether you know it or not, folks who respond poorly, negatively, or not at all, on a consistent basis are creating problems for themselves more than they are for you in that moment. 

For instance, remember the infrequent communicator I mentioned earlier? She said her past dates didn’t think she liked them. Given my experience, I’m pretty sure I know why. I could tell by her tone that this was causing her pain. It was much more painful for her than her seeming lack of interest was to me. 

It always sucks to have these types of things happen, but don’t let it keep you down for too long. Remember, you’re rolling on to other experiences and to find someone else. Some of these folks are likely to repeat their patterns again and again. You don’t need to be a part of that. 

Really. Count your blessings 

First off, the people I mentioned above don’t really seem like those you would want to date do they? A person who ghosts someone without a word, someone who thinks so little of another they can’t be bothered to respond for 24 hours at a time, and another person who feels it necessary to chide someone during their first interaction for following their instructions. 

If you were dating folks who react like this then things probably don’t look up from there. They are giving you their best foot forward and it badly needs some fungicide and a pedicure (because everyone looks better in nail polish). I know in my life letting these folks go has felt like stepping off the tracks in front of a screaming locomotive that is bound to derail. It’s one of those situations where I scratch my head as it passes and ask out loud, “what the heck was that all about?”

So take solace in what is probably a fact, and is certainly the main takeaway from this writing, they weren’t in the same mental space as you anyway. That’s okay. Thank your lucky talisman that you found out in the very beginning. Now you can free up that time and space for someone who can thrive with you. 

It’s okay to be upset

I don’t want you to think for a minute that you can’t grieve or be upset about some of the lost opportunities you’ll have while dating. Some folks you are going to become attached to quickly and your thoughts will drift to the what-if’s. When those connections sour it can make you feel as if you missed out and that can be even harder. Very few people would fault you for feeling that way. 

So by all means take some time to recover if you need. Cry if you feel it necessary as it is wonderfully restorative. Taking time to heal is what will keep you centered in the long run. 

All of this fades in time

There will be a moment when you won’t even remember most of these folks anymore. I know I wouldn’t have remembered the people I spoke of if I hadn’t started this article soon after meeting them. Don’t let the experience stick with you when the faces aren’t likely to. This is one blip in your life that you aren’t likely to remember any more than who sat behind you in second grade. So keep in mind that what bothers you today isn’t likely to do so tomorrow. 

Dating isn’t always easy and there are folks out there who seem to make it their duty to be difficult. Remember though, that things don’t always go according to plan and that’s to be expected. Know that it isn’t about you and that sooner or later you will be back to meet someone else. You’ll keep doing that until one day you’ve found someone special with whom to spend your time. Be kind, be self-aware, and keep your head up; the trains here run around the clock.