I don’t know if there’s really one answer. It’s probably a multi-fold issue—one reason for one person, another reason for someone else. But it usually comes down to a few tendencies, or more often, a combination of tendencies we’ve touched on before. Maybe we’ve talked about how it’s a lethal mix of traits. So let’s revisit the idea of red flags.

There are people who have obvious, glaring problems with relationships or relating to others—and there are people who miss those red flags. They don’t want to see them, for one reason or another. We often talk about these red flags. I’ve even written a paper listing 50 of them. But instead of listing them all, they tend to fall into a few categories. One major category is self-care.

Some people are unable to care for themselves. That could mean they can’t hold a job, engage in self-harm, or struggle with basic responsibilities. Being chronically late is one example—it often leads to bigger issues like not being able to maintain employment or complete an education. Then there’s impulsivity: drinking too much, spending excessively—not occasionally, but habitually. Some people don’t follow the law, cheat, or disregard societal rules. If they don’t respect societal norms, they’re unlikely to respect relationship boundaries either.

Another major red flag is lack of empathy. For example, being late and not caring about your time, or dismissing your concerns. These people don’t take your problems seriously. They can’t do the give-and-take of a relationship. Their needs always come first. They take, but they don’t give. And that’s the opposite of a healthy relationship, which should be a balance of both.

So what happens with people who can’t see the red flags? Often, it boils down to poor critical judgment—the inability to recognize that someone isn’t good for them. I’ve seen this play out in two ways. One is someone who always picks people they feel they need to save or take care of, and then wonders, “Why do I always choose these types?” The other is people who end up in abusive relationships—sometimes more than once.

That pattern shows a breakdown in critical judgment. These individuals are choosing people who have shown red flags, but they choose not to see them. Often, this is tied to guilt. Picking the wrong partner frequently involves excessive or inappropriate guilt.

Take someone who can’t hold a job. The person dating them might think, “Who am I to judge? I’ve had job issues too.” They talk themselves out of their concerns or justify the behavior. It’s a way of coping with guilt—they feel it’s mean to judge. But here’s the thing: “Don’t judge a book by its cover” doesn’t apply here. You should judge people by their behavior. Trust your instincts—they’re usually right.

Your instincts are telling you something for a reason. I always caution parents in session not to force their kids to play with someone if they feel something’s off. We don’t want kids to say that out loud to the person, but we do want them to start listening to their gut—because that’s how we learn to spot red flags.

50% of marriages end in divorce. Second marriages? 75%. Third marriages? 85%. The numbers climb because people keep picking the wrong partners. That guilt plays out in justifying bad behavior, flipping the narrative from “I need to leave” to “I need to help, save, or fix them.” That fairytale ending? It never happens.

People with red flags aren’t easily fixed. It would take several sessions a week for many years to straighten someone out. Red flag behavior is dangerous and difficult to treat. That’s a key distinction.

Now, I get asked this a lot: “Does making a mistake make someone a red flag person?” The answer is no. There’s a difference between a mistake and a red flag. I call it a pink flag. It’s not a red flag until you test it.

Let’s say someone is late. First date, second date—you might think it’s a red flag and walk away. But if you say, “Hey, you’ve been late a couple of times. It bothers me. Is something going on?” and they respond with empathy—“I’m so sorry, I didn’t realize”—then it’s not a red flag. They care. But if they say, “It was only ten minutes,” or blame you—“You’re too uptight”—that’s a red flag.

So it’s a pink flag until you test it. Their response tells you everything. People say, “I need to give them a few months.” No, you don’t. There’s no rule about how long you have to give someone. If someone is rude or inappropriate on the first date, you can walk away. I’ve taught people to say, “Thanks for the drink, nice chatting, but this isn’t going to work,” and leave before dinner arrives.

Why? Because they don’t want to be mistreated—and neither should you. If you’re allowing yourself to be mistreated, that’s a therapy or coaching issue. It’s about boundaries. And that’s another critical factor in choosing the wrong partner.

So, back to the question: “Why am I always choosing the wrong person?” It’s not just about judgment—it’s also about boundary setting. If you struggle to set boundaries and feel like you “have to give someone a chance,” you don’t. You shouldn’t. It’s not healthy. You’re setting yourself up.

It’s also unfair to the other person. If you already know it won’t work, but you go through with it anyway, that’s not empathy—it’s self-sabotage. Being the “better person” doesn’t mean tolerating bad behavior. That’s a fantasy we tell ourselves.

So yes—test the red flag. If it checks out, walk away. Do yourself a favor. Look for pink flags first. Don’t be a statistic. Please pass this on to people who keep choosing the wrong partners. Sometimes they don’t realize it. Just letting them know—“I think this is a red flag person”—might make all the difference.