Real Dating App Stories: 1 Great Date, 1 Awful Date

Woman on terrible date

Some of the best dating app stories come from the worst decisions. At least, that’s what I’ve learned after being on and off multiple dating apps for about ten years. I genuinely believe there is nothing as chaotic and equally rewarding as dating apps. You really get your pick of all the different types of people when you go on a dating app. 

If you’re wondering whether or not to download one of these popular dating apps, allow me to tell you some stories. As someone who’s become all too familiar with dating apps — I was banned from one of them and found my fiancé on another — I’d like to think that all my efforts have made me a kind of dating app expert. 

So here are my two polar opposite stories of a terrible and a perfect first date. 

Dating App Story #1 – The Best Worst Date

Let’s start with the perfect one first because, let’s face it, it’s a bit more boring than the awful one. 

I had known of my fiancé for four years before I was matched with him on Bumble. We had seen each other in passing a few times and even shared a major for over a year. While both of us had taken notice of the other, neither made a move until we saw each other on Bumble. Sometimes, dating apps provide the perfect excuse to ask someone out that you don’t know all that well, but would like to get to know. 

I messaged him with confidence, sure he would remember the one conversation we had four years ago — which I still can recall with absolute clarity to this day. Reader, he has no recollection of this conversation, which still pisses me off. 

But I came out of the gate with my guns blazing, and there was no going back. 

While I attempted to play it off in a cool and collected manner, I knew I had shown my cards too soon. But he was wonderful, and we had an utterly meaningless conversation on the app.

One thing I learned from both of these stories (spoiler alert!) is that the conversation on the app doesn’t matter half as much as you think it does. It seems like the biggest deal. You want to hit all your marks and make the person fall desperately in love with you, but you can also mess up the entire thing or be incredibly dull and still succeed.

I don’t remember a single thing my future husband said when we first messaged him, but I think he talked about his do at some point and sent far too many pictures of him.

On the night we matched, he went ahead and asked me on a date, which was pretty bold, but I respected the gesture. He asked me to meet him at a coffee shop about a week after he messaged me. I said yes, but had no intention of going on that date. While I personally believe going on a coffee date is better than going out to dinner for a first date because it has no pre-determined timer on it, coffee dates gave me a ton of anxiety because I never knew how to conduct myself on them.

But I still messaged him, even though I knew I would inevitably turn him down after a week and, honestly, probably delete Bumble entirely within the next 24 hours. Both of these things did happen, just not in the way I expected.

The next day, he messaged me again to see what my day looked like. When I told him I was shopping for Christmas decorations, he said the magic words every girl wants to hear, “Do you want to go to Target?”

Woman messaging guy on dating app

I had classes for the next three hours, but I agreed to go after. My date made a great move by asking me on a casual and impromptu date. Because I was already out and about for the day, I didn’t have time to stress about getting ready, looking perfect, or even to kindly and matter-of-factly ghost him. Instead, I spent the next two hours studying Chaucer and debating whether or not I was about to walk through the sacred aisle of Target with a potential serial killer.

We met outside of Target and started walking around the store. This was in November of 2020, so we both were wearing masks. Let me tell you, I am thrilled that couples don’t have to wear facemasks on their first dates anymore because it was incredibly awkward. Walking around Target with half of our faces covered in masks that our mothers made for us. Not a great time.

After walking around the store aimlessly for about thirty minutes, I was ready to call it quits, go home, and watch some mindless TV show. Andrew wasn’t quite as ready to call it quits.

The Target we met at was in a giant shopping center with about ten other stores. Andrew used that to his advantage and asked if I wanted to go into another store, then another. Then, eventually, we hit our rhythm and began talking so much that we would walk from one end of the shopping center’s sidewalk to the other.

Three hours later, I had to pick up my roommate’s dog from daycare (my initial escape plan), but I asked if he wanted to join me. He did, we went back to my apartment, and both decided to delete the app and add our phone numbers immediately.

One part of this story I don’t often tell is that I had forgotten his first name for the first three and a half hours of the date. This was yet another factor that should have made everything go terribly wrong. Instead, it made the story cute and very endearing.

While on paper, this date didn’t sound romantic or funny or cute or planned at all (and it wasn’t any of these things, don’t get me wrong), it was the perfect first date. It was casual, simple, and came with little to no warning. It was messy and destined to fail, but yet didn’t, and that’s the magic of it all.

If you’re worried about making each and every first date (or second, third, or fourth date) perfect, don’t be. Sometimes the worst first dates make the best dating app stories and create the best relationships. Love is messy, unplanned, and a little casual. Why not reflect all of that in your first date?

Dating App Story #2 – The Worst Date

And now, the moment you’ve been waiting for, the worst first date I’ve ever been on. In case you haven’t realized a theme yet, things are not always as they appear. You can bomb a conversation on a dating app, have a mediocre first date, and still fall in love. Alternatively, you can have fantastic chemistry on the dating app, have a perfect first date, and end up regretting all your life choices. This is the following story. 

I meet my ex on TinderYes, the dating app from which I am currently banned. No, this is not that story. I matched with him on the fourth of July, and we hit it off. We exchanged witty banter, flirty messages, and a lot of deep late-night chats about everything and nothing. Just like my fiancé, he asked me out right away. But I was, unfortunately, going to be a leader on a mission trip two days later, so I gave him a rain check and kept messaging him.

Anyway, we messaged every night for the week I was on the mission trip. We talked about our lives, beliefs, religion, and basically everything under the sun. I would stay up until about three in the morning talking to him, then wake up at six and start my day.

There’s no sugar-coating it; we had some great conversations.

Once my mission trip was over, he asked me out on a first date. He took me to a swing dancing night. It was the perfect first date, honestly.

It was safe, a group activity, and had no set start or finish time. We both dressed up and drove there separately (safety first!).

When I got there, I noticed that he was a little strange.

The first thing he did was act like he knew everyone around us and all of their backstories, but I would later find that our first date was in a town an hour and a half from where he lived. So in retrospect, the fact that he knew everyone might have been a little flubbed.

woman on a bad date with someone she met on a dating app

The other thing that raised a red flag in my brain was how he talked about himself. He began to tell me that he was the ‘best’ in a number of different things where he came from. He was the ‘best’ in his band (weird flex, but I respect this), he was the best singer, he was the best swing dancer, and he was the best human being the world had ever produced.

Granted, he went to a small Catholic college that enrolled about 300 students. Still, it seemed a little far-fetched.

But I was enamored with him and at least a little intrigued, so I continued on the date. After we were done with swing dancing, he suggested we drive around for a bit and talk. Understand that the logic of me not getting into the same car with him because he was potentially a serial killer had gone out the window. I chose to date this man for a year and a half after this night, so driving around with him for an hour wasn’t the worst decision I would make.

Before we left, he asked if I had a meditation routine. I told him I meditated but didn’t love the app my therapist told me to use. He began to criticize my meditation routine.

Reader, I did not meditate in front of this man. I just told him about the app I used. That’s all.

Anyway, because I was evidently missing a few thousand brain cells, I got in the car with him, and we started to drive.

He then asked what diet I was on. I had made no mention of any diet, and I wasn’t really in the mood to discuss restrictions on a first date. I mentioned that I was trying to be vegan and gluten-free for the summer because I was lactose intolerant, and I was kind of over my unhealthy eating habits; he told me I should also try intermittent fasting. If you’re unfamiliar with intermittent fasting, it’s basically only eating between certain hours of the day. His suggestion was for me to only eat between the hours of noon to six in the evening.

He then asked if I wanted to listen to his favorite barbershop quartet and told me he was in a four-person quartet by himself, where he sang all of the parts. While it ought to have been a red flag that he couldn’t find three other people to sing with him, I wished him luck in his YouTube career and left it at that.

And after all of these beautiful suggestions, he told me that we should date because our chakras aligned and our energy was palpable.

Did I continue to date him after this? Sadly, yes. Writing it down now, I do take full responsibility for that stupidity and not seeing any of those red flags for what they were. Still, I also have a fantastically terrible story to tell, so who’s really winning here?

Whatever You Do, Do It in Love

While it is funny and entertaining to recount these stories through the clear vision that hindsight gives us, it’s also really wonderful to remember that not everything has to be perfect on a dating app. You might be on these apps for five or ten years and have nothing to show for them but some fantastic stories. You also might be on them for five minutes and meet your future spouse.

There’s no one way to do dating apps, and that’s what’s endearing about them. If I were to give you one piece of parting advice, it would be to have fun and not put too much stock in what anything appears to be. Dating should be fun and joyful, and I hope you find that joy in your next encounter.

One more piece of advice for the road: if a man tells you he’s in a barbershop quartet where he sings all of the parts, run.

Abigail Langton
Abigail Langton

Abigail Langton spends her time deep diving into the facts readers want to know about current dating apps online. You'll find her breaking down the latest price points and how to stay secure dating online.