Never Again : A Story about One Girl’s Worst Date in the History of Dates

Actually it was the worst date in history.

Krysty Del
8 min readApr 9, 2021
Adobe Stock Image — Dating

I don’t usually do this but uh… let’s give a little reminder of how much I have grown. I once had the worst date on the planet. Looking back, I can’t believe the situations I used to allow myself to be subjected to. I now see that the date itself never had to happen and had I just asked a few more questions or maybe done a little background diging, I could have avoided the entire situation.

Here is the story of my worst date ever… this one takes the cake by far.

This was maybe 7–8 years ago. I remember it was summer.

We met on Tinder. He was a nice looking brown-skin man. He said he was 30. He was in school for his Master’s degree. He said he was CPD (Chicago Police). He went on to talk about being a homeowner,having a townhouse in Bronzeville. He spoke of his nice car and how he was just looking for someone to add to his life. I probably should have asked more questions, maybe connected on social media

We talked for maybe a week (conversation was totally normal) and then he made a plan, he said let’s meet at Lalo’s for drinks and dinner this weekend and if it goes well we can see where the evening goes. (I should have suggested coffee, something lower key for a first outing.)

I was excited. Now this was before facetime so I couldn’t see him before the date, I could only talk on the phone.

I took my time getting ready because this seemed like it was going to be a really great date. I got my hair done. Nails done too. I even shaved my legs and made sure that my underwear matched. I even wore heels. I was ready… I should have known, whenever I am overly prepared, things have a tendency to go left. However, when I am caught off guard, things in contrast actually go great. Maybe that’s just me.

I arrive at the restaurant like 10–15 minutes early. The restaurant is packed because it is a very popular Mexican restaurant. I text him to let him know there is a wait and if he wanted to go somewhere else. He says no its fine just get a table and he will be there soon. I request a table, get a buzzer and proceed to the bar. I get a margarita and I position myself to face the door so he will see me. A few moments later, he calls again to say that he’s looking for parking so he will be a few minutes late. I tell him no worries, and that my margarita will keep me company.

He arrives and he looks just like his picture. I am so relieved. But something is off. He starts talking but it is quite delayed. I then trying to figure out what the issues is. Is he drunk? High? Is he on the spectrum? He says OMG you look like your photos, my boys thought you were going to be catfish. I said I’m don’t think I’m hot enough to be a catfish but thanks for the compliment. He laughs his delayed laugh. I’m concerned but we continue.

The buzzer buzzes and we proceed to the table. I let him walk in front of me. He trips over the stairs as we walk towards the booths in the back of the restaurant. Behind his back, I mouth HELP ME to the waitress in our section. She winks.

We order, we don’t need menus because its traditional Mexican food. I get a second margarita, he gets a first. I get enchiladas and he orders tacos. Margaritas come quickly. He gulps about half down…

Almost immediately, he begins slurring his words. I’m curious how a man so big and fit could get drunk so quickly. So I start asking questions…

  • Ummm are you okay? Yeah just a little drunk
  • Oh are you a light weight? I mean you only had half? Nah not really…
  • Did you start drinking before the date? Yeah, I drank before, i drank a lot before actually, I mean because I thought you were a catfish or fat and I was going to have to be drunk to get through this.
  • I see. So fat is a deal breaker for you? I mean I don’t like fat chicks.
  • I see… so that must be difficult in your line of work. How is it being a cop? Oh yeah about that. I want to be a cop, that’s why I’m going to school, I’m not a cop yet. I’m a security guard.
  • So what are you getting your masters in that will help with that goal? Uh well, I mean eventually I’ll get an MBA but right now I am getting a criminal justice degree
  • Oh so you are in college and not getting your masters? Where do you go to school? I want to go to DePaul but right now I go to Kennedy King.
  • Oh man that’s quite a trek from Bronzeville, how long is that drive? Oh I don’t drive, well I mean I used to but my license suspended. So I mainly take the bus.
  • But you said you were parking today, did you drive today? Oh that’s because I was late so I got a ride from one of my boys, and I didn’t want you to know.
  • Why were you running late? Because my mom was in the shower.
  • You mom lives in your townhouse with you? Nah, I live with my mom but the basement is mine.
  • Oh so how do you like living in Bronzeville? Oh yeah, I want to live there eventually but I stay in Englewood.

The food comes, and at this point I’m over this date. The waitress can see the look of panic in my eyes. She offers to wrap up half my food. He places his wallet on the table and says don’t worry boo I’m paying for this.

He take a few more sips of his margarita and a few bites and leans back a little too far. He passes out.

I motion for the waitress. She wraps up my entire order, and puts my margarita in a to-go cup. Since his wallet was on the table, we take out enough to pay the meal, and tip the waitress and I leave. She says she won’t tell him I left.

I walk the block to Roosevelt (The closest main street) and I am sitting on the bus stop contemplating life. (I don’t drive and this is pre-uber) I remember the bus was 12 minutes away, and I was finishing up my margarita. I look up and he’s running towards me.

I guess he woke up and realized I was gone, he got his food and chased after me.

He’s like you should kiss me. I’m like whelp I guess I’m not waiting for the bus. I start walking East on Roosevelt Road towards the trains (about a 1.5 mile walk).

He starts following me, yelling at me to kiss him. But he’s drunk that he’s zig zagging. I am speed walking over the bridge and he catches up to me, attempts to kiss me, I push him off and then starts to veer off into traffic. He stops himself at the curb, and then runs after me again. He catches up to me and tries hold my hand. I jerk my hand away and veers off into traffic again. He couldn’t walk in a straight line and at this point I am speed walking up a hill. I get about halfway over the Roosevelt bridge, when he yells at me to wait because he has to do something. Something tells me to look. I peer over my shoulder and this man unzips his pants in clear view of traffic. He whips out his dick stumbles to the edge of the bridge and stands on his tippy toes. He pees over the bridge while singing (I’m gonna kiss you). I take that moment to run. I probably should have flagged down a car or crossed the street to the shopping center but I chose to run instead.

I ran. I ran all the way over the rest of that bridge right into the large train intersection at Roosevelt and State. I swiped my card and got on the train.

Fast-forward to last year…

I was on Facebook and at the bottom of the screen they have people you may know. I see a face that looks familiar. It was the him. I swear Facebook must tell people when you look at their profiles, because he messaged me and asked did we ever go to Lalos together because I looked familiar.

I hit block.

Now 2021 Krysty would have walked out when he showed up drunk. Life is too short for such nonsense. I would have either gone to the bar around the corner laughed it off, and then caught a cab home or I would have went to the bathroom and stayed there until the waitress could get my coat and called someone to come get me. I wonder why I sat through the date, maybe I wanted to see just how bad it would get. It’s in moments like these we learn who we truly are, and apparently I was ripe for the bullshit. I always used to think why do these happen to me, it’s because I was being too nice. I get it, we live in scary times and I don’t know what a man is capable of, but make the best decision that you can at that time.

I was once downtown Chicago shopping and a random man followed me for 2–3 blocks, and I kept turning streets and he stayed behind me. I got to the corner and yelled at the top of lungs


People on the sidewalk stopped to help. He replied “ damn, I just thought you were cute”, and I responded “so following me in and out of businesses for blocks is not how you get my attention”. He crossed the street.

You don’t have to be nice and respectful in scary situations! Get out becasue your safety is what is most important. Take the number if you have to, but cross the street, scream, and worry what people will think later, plus you don’t owe them a damn thing. What if that first man had assaulted me on the street?What if that second man had grabbed me? This would be a very different stories versus just a crazy memory. The lesson in all of this is to not be like me, cuss that man out, make a scene if you have to, and most importantly make it home safely.



Krysty Del

I’m just a girl standing in front of her computer asking you to read her. A writer of wrongs. A place where psychology, dating, politics, and fashion meet.