Red Flags & the Third Worst Date in History

Crystal Jackson

When I say I had the worst date, I’m not talking about a calendar date. This isn’t an essay about a particular historical event. I mean date as the social occasion. I’m referring to my personal list and the third-worst date I’ve ever been on. But I also want to talk about the glaring red flags that heralded it.

We’ve all got them. Red flags, I mean. After all, none of us are perfect matches for everyone. There are going to be things about us that set off red flags for someone else because they’re just not on the same page. We want what we want, and there’s nothing wrong with that.

What continues to astound me are the red flags that we have that are actually things we could work on, but don’t. These are the behaviors that aren’t healthy and could be fixed, if we were remotely interested in doing so — and self-aware enough to acknowledge them.

Which brings me to the 3rd worst date ever.

I understand that it likely pales in comparison to the many horrible dates that have been experienced, and at least my safety wasn’t a problem, as far as I’m aware. Still, bad dates and red flags. That’s what you’re here for, right?

Here’s the thing about me and red flags: I know very well what mine are, and I know very well how to spot them in other people. Which is all well and good. But I can’t do anything about the fact that someone else might state a deal-breaker and then compromise their own values to try to see it through, particularly when they aren’t honest with me. When they are honest with me that I’ve raised a red flag for them and still try to compromise that value, that’s when the red flag is set off for me.

So, I’m on this date with someone I had a day or so of steady communication with- yes, from a dating app. I had a free night, so we made plans for dinner. Things seemed to be going well, but a couple of things had come up in those conversations that I wanted to clarify before it went any further.

There we are, at dinner, and the conversation went to some of those areas. I decided to seek clarification on a point he mentioned. He’d mentioned a deal-breaker, and when I said that we weren’t on the same page, he dialed it back and said it wasn’t really a deal-breaker after all. Then, the tone changed.

Why was I being so negative? Why would I waste his time and meet him if I had concerns? Why wasn’t I feeling the connection he thought was so apparent? You get the picture.

It was as if he stood upon the table and began to wave about red flags.

That’s how extreme his reaction was to a simple line of inquiry. It wasn’t an interrogation. I just asked if he’d considered his value against my stated difference in values. Next thing I know, out comes the story of the time he spent in prison. Then, he brings up the recent DUI he had, all the while sipping his adult beverage and discussing his (past?) history of addiction.

Between these stories, he’s escalating because I’m not responding to all of these disclosures with cheerfulness, support, and attraction. Instead, I’m feeling some understandable concern, especially since I’m treated to a monologue on why he’s a fantastic person and what our life together will look like when he hasn’t really paused in his soliloquy to get to know me as a person or ask what I want for my life.

Clearly, the Universe was trying to get my attention.

It was reminding me that I have a hard time standing up for myself. Often, I am fierce in my defense of everyone else in the world, but I’m stuck on the Polite setting when it comes to defending myself, and I have a hard time shifting into Boy Bye. Let me give an example of what this looked like on the 3rd worst date of my life.

I ask the server about the location of the restroom during the course of dinner. I excuse myself to use this restroom. My date immediately wants to know why.


Yes. Why.

Why do you need to go to the restroom? He looks over at my glass of water and margarita and then back at me. I’m standing there, my body turned eagerly in the direction the server said to go. I can’t believe what I’m hearing. I must have misunderstood.

I’ve been waiting for this. He says it with a straight face, growing increasingly irritated.

For me to use the restroom? I don’t know what’s happening here, but I need to go. Now. Five minutes ago would have been ideal. Is this conversation really happening?

Did you have something else to drink when you first got to the restaurant? He looks back at my water and margarita with suspicion. Desperate to continue in the direction of the restroom, I tell him that I had an entire glass of water at the table before he arrived.

Lies! All lies!

I did not, in fact, have a second glass of water. I hate lies and liars, but I needed the ladies’ room with some urgency, and it seemed the most expedient way to get there. I had justified my need to use the facilities. He nodded his head as if in understanding, and I moved quickly before he could come up with another objection.

If your head is spinning, imagine mine! Imagine it further when I get back to the table where I’m asked why exactly it took me so long. Significant pause. While my brain tried to process what exactly he was implying, he then clarifies: Were you in there primping?

Now I didn’t owe him an explanation about my bathroom habits, and I certainly don’t owe you one either. But, for the sake of your entertainment, I’ll explain.

Ladies' rooms have lines. This is a well-known fact. It’s so well-documented that it’s not even something that is up for dispute. They have lines. Period. End of discussion.

Beyond that, I had to wait for a woman to finish up a phone conversation while she was simultaneously peeing before I could be allowed to use the one non-disgusting stall (although a phone conversation while using the facilities is gross enough on its own).

And I didn’t primp, as a matter of fact. I’m not sure if I’ve ever primped. I washed my hands for an appropriate amount of time like people do. I also shot off three quick text messages to let some friends know that I was safe but needed to get the hell out of there. I turned down three immediate offers of a rescue call and said I would figure it out.

So, there I am, sitting in front of this guy who wants to know why I was in the restroom for all of five minutes. Then he returns to his rant about how great he is, how lucky I would be to have him, and why did I waste his time if I was concerned that we might not be compatible. Of course, he completely glosses over the fact that I wasn’t, until that very hour, privy to the details of his time in prison, subsequent sketchy history, recent arrest, new religious conversion, and total lack of boundaries. In fact, he’d been charming enough up until the actual date when the truth came spewing out.

He knows now that all is lost. There will not be another date. So he assesses the possibility for sex instead, but then reminds me that he’s not into one-night stands, so I would have to commit to having sex with him at least one more time. I don’t remember agreeing to it the first time. Because I didn’t. I turned that offer down as politely as I could manage and got out of there with as much speed as my high heels and the rainy weather would allow.

Clearly, my boundaries and ability to speak up for myself need a little fine-tuning.

Which brings me to the subject of red flags.

Yes, we all have them. I don’t want to date a smoker, which is probably a red flag for smokers. I have kids, young ones, which might be a red flag for someone else. I’m sure I even have a whole host of personality quirks that some people aren’t into. Fine. Great. I’m not everyone’s cup of tea, and I’m not trying to be.

We should all be more self-aware.

I am trying to be self-aware. I know my faults and flaws as well as my strengths, often better. I take that self-awareness into my dating experiences. I know what I want and what I don’t, and I don’t misrepresent myself. I don’t even try to put my best foot forward. I just try to be as real as I can be, so that the other person is fully aware of what I bring to the table. I’ve done my inner work, and I’ll keep doing it. I’m not lugging around baggage, and I don’t think it’s asking too much to want to date someone on the same level.

We need to know what red flags are and discover our own.

If we’ve been dating for more than a minute and a half, we’ve had some time to figure out all the dating behaviors that we hate. But what about the ones we participate in that other people hate? We need to quit playing games and figure out which of our behaviors are red flags for other people- not to manipulate them, but to bring some awareness into how we interact with others.

Some people are masters at self-sabotage.

They’d be great partners if they weren’t sending out all the wrong signals that aren’t even representative of who they are. When they realize this, they can actually do some work to deal with the issues that just might be ruining their chances at happiness with a strong partner.

Others don’t even know what a red flag is and certainly don’t realize the half a dozen red flags they’re waving at any given moment.

Red flags are those negative traits and behaviors that other people should be wary of. They’re basically the signposts of future issues in the relationship, should it continue. They should always be heeded, but most of us just keep on trucking.

If we have baggage, we need to unpack that mess.

No one else is going to do it for us- outside of a professional therapist, maybe, and even then we have to do it ourselves while they assist. If we’ve figured out we have some issues, we need to work on them rather than expecting to find a partner who will just put up with, frankly, garbage behavior because we’re too lazy to do the work.

If we have some major red flags that can’t be fixed, we need to be upfront about them.

Prison falls into this category. Lots of people are going to have a problem with a history that involves time spent in prison. No one can go back and make that experience not happen, but we can all be upfront about the big red flags sitting around in our past. That’s big-deal information that needs to be volunteered upfront. The right person won’t care, and the wrong one can opt out before it gets dropped between drinks on a date that wasted time for both of us.

If someone calls out a red flag, we need to accept rather than defend.

Everyone has the things they want and don’t. If something comes up that the other party isn’t okay with having in their lives, we need to be respectful enough to have some level of acceptance about that. We don’t have to agree with it. We don’t have to like it. But everyone has the right to say no, and no is a complete sentence.

We’re not owed an explanation, and getting defensive because the other person has decided we’re not for them is foolish and a waste of time. We’re entitled to our feelings, but they’re entitled to say that they’re just not into us without having to hear any complaints, wheedling, justification, or recriminations. And vice versa.

The 3rd date wasn’t bad because of his past.

At least, not solely because of it. It was bad because of how he handled the most basic conversation that flowed into what he considered a “negative” area, like questioning if we were on the same page about something he’d mentioned as being important to him. He wanted me to be The One because he liked my face and had decided that I would be perfect for him and had no interest in discovering that he was far from perfect for me.

It was bad because he thought it was appropriate to have a monologue about my bathroom habits and actually interrogated me before and after my trip to the restroom. If he’d been able to get in there, I might have been interrogated during, too. We can only speculate, thank goodness.

It was bad because he managed to drop an incredible amount of both misogyny and jealousy in the space of a short dinner. Any mention of even having an ex (I have kids, and they didn’t get here through the cabbage patch) made him see red. I’m an adult, and I expect people to have a past. I wasn’t giving him a blow-by-blow of it, and yet he was still deeply affected by the fact that I had a past at all.

It was bad because he seemed to think that monopolizing the conversation with his grandiose ideas of himself, his future, and how our fictional relationship would proceed was appropriate. Dating should be a give and take where both parties are interested in getting to know the other person. Actually, this was another red flag because it’s consistent with an addiction, a fact I know well from my time as an addiction counselor. It also had some markers of narcissism.

It was bad because of how he tried to gaslight me into thinking that the date not working out was entirely my fault for not canceling because of a vague concern about something he’d mentioned rather than because he’d failed to disclose a significant amount of information. He went on the attack and continued to make comments that attributed negative characteristics to me rather than taking any ownership of the outcome of what was a truly awkward and uncomfortable evening that even margaritas couldn’t improve.

Beyond that, there was no chemistry. None. The potential for a relationship would have failed anyway, but it didn’t have to be a bad date.

In fact, I once went out on a very similar date with someone else. It was the same type of restaurant setting and a similar setup. The guy I met that time actually had a lot of baggage, but he was entirely upfront about it, incredibly self-aware, and was able to talk about it with total ownership of his own role in the things that had happened in his life. It was impressive.

Added to that, he was extremely attractive. But there was no chemistry. Still, it wasn’t a bad date. In fact, it was pretty great. We had good food and good conversation, and we both accepted that it wasn’t going to be anything. No one had hard feelings about it. We were respectful to each other, and the evening ended peacefully.

Red flags don’t make bad dates; how we handle them does.

The fact that I’m polite shouldn’t be a problem, in an ideal world. It has become a problem because I’m polite at the risk of putting myself in harm’s way or enduring an evening in someone’s company who isn’t being remotely respectful to me. I’m working on it.

Red flags don’t make the dates bad. It’s all about how we handle them. When they come up and we see that it isn’t working out, we can either end the date then without bitterness, or we can choose to enjoy the evening by having a good conversation on other topics before heading our separate ways. There’s no reason whatsoever to treat someone else like their red flags aren’t important. After all, they are important to them.

We all have red flag behaviors for a reason, often from past experience and having learned the hard way. That’s okay. What isn’t okay is to be on the receiving end of verbal abuse because someone else takes issue with what we do (and don’t) want in a partner.

I may change up the ranking, but for now, that was my third worst date ever. It ranks somewhere below the mansplainer who mansplained to me why I should expect and even appreciate sexual harassment and the catfisher who interviewed me to be his child’s stepmother while lecturing me on the appropriateness of my life choices. I would really like to keep it to three and only have pleasant dates from now on. But the Universe seems to take perverse pleasure in teaching me things the hard way, and I can name about half a dozen friends who just read this for their own entertainment (I don’t blame you; it’s funny now, just not when it was happening).

Red flags don’t have to end in bad dates, but it actually helps if we know what a red flag is and have any level of self-awareness. Also, maybe don’t ask dates about bathroom habits. One might consider that to be rude.

Beyond that, setting realistic expectations to get to know someone else and see how it goes might be a better predictor of success than planning the entire relationship out in your head in advance and then trying to make the other person live up to it.

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Crystal Jackson is a former therapist turned writer. She is the author of the Heart of Madison series and a volume of poetry entitled My Words Are Whiskey. Her work has been featured on Medium, Elite Daily, Thought Catalog, The Good Men Project, and Elephant Journal. When she's not writing, you can find her traveling, paddle boarding, cycling, throwing axes badly but with terrifying enthusiasm, hiking, or curled up with her nose in a book in Madison, Georgia, where she lives with one puppy and two wild and wonderful children. Crystal writes about relationships, mental health, parenting, social justice, and more. Never miss an update. Subscribe to emails:

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