7 Self-Sabotaging Behaviors to Avoid in Dating

I used to have a reputation among my friends as a serial dater. It was like my second job, which explains why I eventually became a dating coach!

After years of doing the self-reflection work and guiding singles to finding lasting love through my Conscious Dating process, I’ve discovered several self-sabotaging behaviors that can ruin even the most promising dates.

I’m happily married now, but I’ve been guilty of a few mistakes in the past when I was dating, and I’ve seen the mistakes on some of my not-so-great dates. We all have these little unconscious habits that can completely mess up our dating lives without knowing.

It’s easy to see the faults in others. It’s a lot harder to see them in ourselves. The truth is that self-sabotaging behaviors are coping mechanisms. We’re all just trying to protect ourselves from getting hurt. Sometimes, we don’t even realize how our actions affect those around us.

As a recovering people-pleaser, I’d say this is one of the hardest habits to break. Overthinking is the ultimate connection killer. When we overthink, we create problems that don’t actually exist.

I remember going on a date with someone I really liked a lot. I put him up on a pedestal, and my head was spinning during our date. I couldn’t stay present to even remember the things he was saying.

I was so worried about being witty enough, interesting enough, or fun enough. There was a lot of “I’m not enough,” and guess what? That was the energy that appeared while I was on the date. Not the most authentic or confident version of myself.

The thing is, overthinking leads to a self-fulfilling prophecy. If you’re constantly looking for the worst-case scenario, thinking, “They’ll never like me.” You’ll probably make that belief come true!

I’ve watched people fall into nervous chatter or make self-deprecating jokes that push potential partners away because, deep down, they’re thinking, “I’ll reject them before they can reject me.”

Honestly, you can’t predict the future. So stop spinning in your head and start being present in your heart. A trick I tell my clients to do is to make the date about brightening the person’s day across from you. It will help you stop the chatter in your head and move the focus from YOU to THEM.

Remember, the key to building a connection is to be fully present with the person sitting across from you. They are there because they want to get to know you, so have confidence that you are enough.

I’m a pretty good listener, which I believe is a strength, but it can quickly become a weakness on dates with the complainer. 

Some downer daters would talk about their terrible online dating experiences or how horrible all their recent dates had been. It would drain all my energy listening to them. 

I recommend avoiding these types of conversations at all costs, even if the last person you dated really did show up 45 minutes late and then talked about their mother the entire time! 

You might think this is a way to connect, but it only leaves people thinking how bitter and negative you are.

The past dates that left me with a positive first impression always focused on conversations about what made them happy. My tip is to stick to what is exciting and positive in your life, and keep the conversation light and fun. 

Do you know what’s attractive? Talk about the things that bring you joy! Love live music? Share the story about the amazing concert you went to last weekend. Have a passion for travel? Talk about your next trip to Thailand!

And if you have a rough day. I don’t think you’re being “too much” by mentioning that you genuinely had a difficult day. It’s okay to talk about it briefly. Just be sure to move on to more uplifting topics that make you smile and feel at ease.

It’s a common habit to speak more than we listen, especially when we are nervous. But the point of going on a date is to get to know someone and make a genuine connection. 

How are you going to do that if you don’t ask questions and truly listen to your date’s responses? 

It’s not just polite; it shows you’re genuinely interested in getting to know them beyond surface-level chit-chat.

I once went on a date with someone who talked at me the entire time. He could have replaced me with anyone, and he would have had the same conversation. Not one question was asked about me. At the end of the date, he said, “I had so much fun! Let’s do this again.”

No thanks! 

Of course, he had fun — the whole conversation was all about HIM. The date was such a turn-off. He knew absolutely nothing about me by the end.

Remember, we have two ears and one mouth. Aim to spend 70% of your time listening and asking questions and 30% of your time talking about yourself. This should be a dance where you both take turns; your date should be asking about you, too!

I’m definitely guilty of this one. I used to think if I shared all the red flags I wanted to avoid with my date, I would cover my bases and not repeat them. Big mistake!

Talking about my exes made it seem like I wasn’t over them. It gave the impression that I was still carrying the hurts from my last relationship and not ready to move forward. It also sent a message that the person sitting across from me wasn’t as important.

I remember one date when we both shared war stories about our crazy exes. It felt like a bonding moment at first, but quickly, it became more like a group therapy session. We left feeling pretty down and defeated. 

Needless to say, there wasn’t another date.

Now, after a few dates, it is appropriate to discuss what you learned from past relationships. The key word is “learned.” Avoid shaming and blaming your ex. When you place all the blame on someone else and take zero accountability, you come off as someone who lacks self-awareness.

One of the biggest self-sabotaging behaviors I see in the dating world is what I call the “Marketing Trap.” This happens when a person is trying to be someone they’re not. I used to fall for this trap when I was in people-pleasing mode. Thinking I needed to be a certain way to win someone over.

I came off as inauthentic and often felt like a bait-and-switch for someone dating me. If my date liked tennis, so did I. If he loved football, I’d wear his team shirt (knowing nothing about football). I never created genuine connections by approaching dating this way.

Eventually, I couldn’t keep the charade going, and the person I was dating would see the real me and lose interest.

I learned how to stop pretending to be someone else. I realized the person sitting across from me wanted to get to know the real me, not some version I thought they’d like better. I stopped claiming to love things that I didn’t. I began to be more honest with who I was. I owned my truths.

Do you know what that brought me? More authentic relationships, not only in dating but in friendships, too! Being authentic acts as a natural filtering system to bring the right people into your life.

In my Conscious Dating process, I teach clients to be the chooser rather than the chosen. Instead of morphing yourself to fit someone else’s ideal, focus on whether you like this person. I have my clients ask themselves: “Does this person have the qualities that make a great partner? Do they make me feel accepted and safe?”

Remember, you are worth getting to know. The person sitting across from you is there because they want to meet YOU. So, be authentic and genuine from the start!

I’m sure you’ve met a braggadocios date a time or two! Excessive bragging is one of the biggest turn-offs in dating, and I’ve seen it sink countless connections.

A person gets caught up thinking their worth is tied to listing all their accomplishments, possessions, and status symbols. It comes across as insecure and self-centered.

I’ll never forget this one date where the guy mentioned the price of his watch, what kind of car he drove, and his career achievements within the first 15 minutes. By the time he started name-dropping celebrities he’d met, I was out!

I believe true confidence is quiet. It doesn’t need to announce itself. Instead of bragging, I would have loved hearing about his values through life stories. 

My recommendation is to avoid bragging to your date about how generous you are; instead, mention the community garden where you volunteer. Don’t boast about your successful career. Talk about what you find meaningful about your work.

Remember, you are more than your accomplishments and the superficial things you own.

One of the most frustrating experiences when I was in the dating world was meeting the “Avoider.” You know the type? Just when things start getting good and the connection deepens, where real potential appears, the person you’re dating starts looking for everything wrong with you.

It’s frustrating because you can see the relationship blossoming, you’re excited, and then BAM! The person starts nitpicking at the little incidental stuff that really doesn’t make or break the relationship. They fixate on the problems that don’t really exist just to avoid getting too close to you.

I experienced the Avoider firsthand; I dated a guy I thought was wonderful for about two months. Everything was going great until I started opening up about my feelings for him. I was vulnerable and said, “These are the best two months in a relationship I’ve ever felt.” He said he felt the same. 

Then, suddenly, his texts became sporadic, and his workload mysteriously increased. He told me he didn’t like the way I did the dishes! Here’s the kicker: he decided to end the relationship via text. It was heartbreaking, and I felt completely blindsided. 

Looking back, I realized it wasn’t my fault. Being vulnerable shouldn’t scare someone who really cared for me. The fact that he ran to the hills made me realize that he wasn’t going to let me in, so instead of letting intimacy build, he created every reason to push me away.

My feelings were really hurt, being on the receiving end of the Avoider.

I know vulnerability is scary for most of us, but I believe it is essential to create a deep connection. Trust me, if you’re an Avoider, people can feel when you are keeping one foot out the door.

The most devastating part is that you will never fully experience the profound intimacy that comes from truly letting someone in if you keep that behavior going. 

Each of these experiences taught me a great lesson about self-awareness. We are all doing the best we can with what we are given. 

Can you make self-sabotaging behaviors disappear forever? Of course not! We are human, imperfect, and make mistakes. But the goal is that with each experience, when we know better, we can do better. 

I believe that every day, we get a chance to practice showing up as our authentic selves, reflect on our challenges, and learn how to do things differently the next time. If I can do it, you can too! I believe in you.