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Four Things You Should Take Away from Bad Dating Experiences

A girl and a guy who used to have bad dating experiences, laughing and kissing on the beach.

I matched with Ryan on a dating app. He was a tattooed redhead and looked dorky and cute in his photos. I’d just started dating online and hadn’t gone on very many dates yet. But, so far, I’d been lucky. I’d gone out with a doctor and a filmmaker. Both had been nice men and we’d had nice times, but nothing much had come of them. Since I hadn’t dated in over ten years, I didn’t really know what I was looking for, so I was willing to try everything. Even though Ryan didn’t look like the kind of guy I’d normally be into, I gave him a shot.

Once we matched, he was quick to compliment me, and we seemed to have some things in common. We both loved reading and shared a fair number of favorite authors. After chatting, he opted to meet me at a coffee shop during the only hour I had free that day, though it would take him over 30 minutes to get there. It seemed ridiculous that he was going to waste so much of his time just to see me for an hour, but I thought, why not? 

“I’m wearing my jammies. I think you’ll like them,” he texted me once we made concrete plans to meet at the Starbucks near my work.

“Haha,” I responded. Thinking,  Oh, he couldn’t possibly be wearing those.

Oh, but he did. He had large Spongebob bottoms complete with giant paw slippers and a backpack bedecked with keychains and patches. I wish I was joking.

He also didn’t look very cute in person. Looking back at his profile after the date, I realized most of his photos showed him from a distance and that some of the photos had been taken years earlier or from, ahem, somewhat forgiving angles.

When I saw him come in the door and look for me, I only knew it was him because he’d texted me right before he was coming in. When I met his eyes, I breathed in deeply, said “hello,” and proceeded to have a forty-five minute conversation about the book he’d been writing based on Norse mythology. At the end of the date, I gave him a side hug, said, “Nice meeting you!” and fled to my car. When he tried to make further plans, I let him know I wasn’t interested.

We’ve all had our share of bad dates, especially while online dating. Sometimes you never really know what you’re going to get, even after you’ve done your due diligence and screened out the weirdos. (And, to be clear, I had not done mine with this fellow).

But we can also focus on the things we should be taking away from these bad dating experiences. Because every experience is a learning one, right?

A Sense of Humor
After my date with Ryan I immediately called my best friend and the two of us laughed and laughed over the ridiculous details together. 

Dating is hard. We’ve all had those experiences where we think it’s going to be great and then it soooo isn’t. Try to keep things light. If anything, you need to be able to laugh and learn from your mistakes. After my experience, I learned to be cautious about guys who were too overzealous. If a guy was willing to drop everything to see me that exact moment, he probably had some qualities I wouldn’t be all that interested in. (Like a job, hobbies, a life outside dating, etc.) I also got a great story to tell my friend and an even better laugh out of it.

I went on several bad dates before I met my current partner, and the most important thing I learned was to practice empathy. We’re all trying to find love eventually, and we all have a story to tell. Some of the men I went out with were desperately sad and lonely, and I just listened and left understanding their story and my own a little better. 

Now, to be clear, I went on a couple of dates with not nice men. I could practice empathy with them, but there’s a difference between practicing empathy and getting abused. Like the guy who tried to yell at me because he didn’t “believe” in white male privilege? I could understand where he was coming from (or where he thought he was coming from), but that date quickly ended. 

A lot of daters are just a little too nice. Sometimes when you think you’re being nice to someone, you’re actually sending mixed signals and not doing anyone any favors. It can seem easier to slip into not being clear because you don’t want to hurt someone’s feelings while dating, but it’s really the cowards way out. You don’t always have to do it in person, but at least send a text that says, “Hey, you’re really nice and I had a nice time, but I’m just not interested.” You’ll be surprised by how many people appreciate it.

A YOLO Attitude
You may have been dating a while, or for just a short time, but you never know what’s going to happen. My bad experiences could have easily made me give up online dating. But I’d been through an awful divorce, and I wanted to have some fun and see what was out there. When a date was bad, I just shrugged and scheduled the next one. You might not end up meeting the love of your life, but you might enjoy your time with someone, do something fun, and learn something more about yourself and what you want. 

It’s easy to get disheartened when dating doesn’t go your way, so instead stay focused on what you can control. By the time I met my serious honey, I was a seasoned online dating veteran and I walked into my first date with him with all of the above qualities. That meant I could treat the whole date lightly, actively listen, be clear that I was interested, and not be a stage four clinger either. Dating is hard, but it doesn’t have to be hard for you.

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