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Avoid These Self-Sabotaging Behaviors on Dates

We all have unconscious habits that sometimes can wreak havoc on our dating lives and turn off the best of dates.

Self-sabotaging behaviors can show up as a coping behavior to help us protect ourselves from being hurt or lack awareness of how our actions affect others.

Today we will discuss five self-sabotaging behaviors to avoid on dates, so you can have a better chance at finding that special someone.

Overthinking Everything

Overthinking can lead to paralysis by analysis. When we overthink everything, we start to see problems where there aren’t any.

Instead of letting the conversation flow and enjoying the moment, we start to worry about whether we’re being witty enough or if we look awkward.

Of course this behavior only leads to a self-fulfilling prophecy. If you are looking at the worst-case scenario every time, you may unconsciously self-sabotage the opportunity to save your heart from being broken.

We might pick up a nervous chatter or start thinking this person isn’t going to like me anyway, so we’ll make some off-color joke to push them away. The attitude of “I’ll dump them before they can dump me.”

In reality, you can’t predict the future. Try to focus on the present, stop going to the future or the past. This behavior only keeps you stuck in one place. Learn how to be present with the person in front of you, and trust that the worst-case scenario rarely happens.

Bringing Up the Ex on the First Date

Talking about your ex too much on a first date is a huge no-no. It makes you look like you’re not over them and that you’re not ready to move on. It also sends the message that the person sitting across from you is not as important as your ex.

However, after a few dates, it is appropriate to discuss what you learned from your past relationships.

It is important to avoid shaming and blaming your ex. When you blame and don’t take accountability for the part you played in the relationship’s failure, you come off as a person who lacks self-awareness.

Share what you learned and what you would do differently this time around. Your accountability helps your date see that you have grown from the experience.

Being Negative

Nobody wants to go on a date with a negative Nancy. Being negative can bring down the mood and make the other person feel uncomfortable. Avoid complaining about how horrible your dates have been or how your online dating experience sucks.

Try to stay positive and keep the conversation light and fun. Talk about what inspires you and things you are passionate about. Love live music? Talk about the last concert you went to.

If you’re having a bad day, it’s okay to mention it (only spend a few minutes), but try to move on to more positive topics that make you both laugh and feel at ease.

Want even more signs you may be self-sabotaging your relationship? Check out this video! (Article Continued Below).

Speaking More than Listening on a Date

When we’re nervous or uncertain, it’s common to talk more than listen on a date. But if we want to make a genuine connection, it’s important to ask meaningful questions and truly listen to our date’s stories and perspectives.

It’s not only polite, but it shows that we’re interested in getting to know them beyond surface level conversations. They say we have two ears and one mouth, so spend 80% of the time listening and 20% of the time asking questions. Remember the dance is that you both switch up, and your date should be asking you questions as well.

By striking a balance between asking and listening, we can create a comfortable and engaging environment for great conversations to take place. Let’s ditch the monologue and dive into the art of asking thoughtful questions.

Not Being Yourself

One of the biggest self-sabotaging behaviors is not being true to yourself. Most singles I work with fall into the Marketing Trap. When we try to be someone we’re not, we come across as insincere and inauthentic.

The person in front of you wants to get to know the real you, not some version that you think they’ll like better. Don’t pretend to play tennis if you don’t like it. Own who you are. It acts as a filtering system to bring the right person into your life.

In my Conscious Dating Programs, you learn how to be the chooser. Rather than morphing yourself to fit someone’s narrative, focus on whether you like this person or not. You should ask yourself, “Does this person have the qualities that make a great partner? Do they make me feel accepted and safe around them?”

So, be authentic and focus on screening them based on the values you are looking for rather than trying to impress them.

Remember, you are worth getting to know. Invest your time in creating self-awareness of sabotaging behaviors. The more conscious you become you will attract the same because like attracts like.

The person sitting across from you is there because they want to get to know you. So, take a deep breath, relax, and have fun! If you need support in breaking your self-sabotaging behaviors, I’m here to help. Book a Free Relationship Readiness Review call with me here. 

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I’m thrilled 🎉 to share that I was a guest on a podcast all about dating as a woman in your thirties and up! The episode will be released very soon, and I’m really excited for you all to hear it.

During our conversation, we dove into the unique challenges, opportunities, and experiences of navigating the dating world at this stage of life. We discussed everything from modern dating apps to relationship expectations and finding confidence in yourself while searching for meaningful connections.

Stay tuned for more details about when and where you can listen to the episode. If you’re interested in dating perspectives for women in their thirties and up, or know someone who might benefit from this conversation, you won’t want to miss it!

I can’t wait for you to hear the insights we shared!​​​​​​​​​​​​​​​!​​​​​​​​​​​​​​​​

#DatingAfter30 #MidlifeDating #DatingInYour40s #DatingPodcast #ModernDating #SingleAndThriving #DatingAdvice #RelationshipTalk #DatingJourney #WomenWhoDate #DatingReality #AuthenticDating #LoveAfter30 #DatingExperience #SingleLife #MatureRelationships #DatingAppLife #FindingLoveAtAnyAge #DatingWithConfidence #PodcastGuest
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I’m thrilled 🎉 to share that I was a guest on a podcast all about dating as a woman in your thirties and up! The episode will be released very soon, and I’m really excited for you all to hear it. During our conversation, we dove into the unique challenges, opportunities, and experiences of navigating the dating world at this stage of life. We discussed everything from modern dating apps to relationship expectations and finding confidence in yourself while searching for meaningful connections. Stay tuned for more details about when and where you can listen to the episode. If you’re interested in dating perspectives for women in their thirties and up, or know someone who might benefit from this conversation, you won’t want to miss it! I can’t wait for you to hear the insights we shared!​​​​​​​​​​​​​​​!​​​​​​​​​​​​​​​​ #DatingAfter30 #MidlifeDating #DatingInYour40s #DatingPodcast #ModernDating #SingleAndThriving #DatingAdvice #RelationshipTalk #DatingJourney #WomenWhoDate #DatingReality #AuthenticDating #LoveAfter30 #DatingExperience #SingleLife #MatureRelationships #DatingAppLife #FindingLoveAtAnyAge #DatingWithConfidence #PodcastGuest
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Speak Up to Express Your Needs! Ever notice how waiting for “the right time” to express your needs often means they never get addressed? I share my journey of realizing that while we should avoid conversations when emotions are flooding, consistently postponing our needs leads to dangerous resentment. Learn the balance between giving space during heightened emotions and still honoring your boundaries through calm, intentional conflict. Discover how speaking up prevents resentment while still respecting emotional states—a critical skill for healthier relationships. #RelationshipAdvice #HealthyBoundaries #ExpressingNeeds #EmotionalRegulation #PreventingResentment #HealthyConflict #RelationshipCommunication #EmotionalIntelligence #SettingBoundaries #ConflictResolution #RelationshipTips #EmotionalFlooding #PersonalGrowth #RelationshipPsychology #CalmDiscussions #AvoidingResentment #HealthyArguing #RelationshipHealing #CommunicationSkills #EmotionalAwareness
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When we truly become still and listen to understand others, something magical happens. By setting aside our mental chatter and focusing completely on what someone else is saying, we create a space of genuine connection. Active listening isn’t just waiting for your turn to speak. It’s being fully present—noticing not just their words, but their tone, their body language, what remains unsaid. When we listen this deeply to others, we’re actually strengthening our ability to tune into our own inner voice. Think about it: each time you quiet your mind to truly hear someone else, you’re practicing the very skill needed to hear yourself clearly. The mental stillness required for deep listening becomes a pathway to self-understanding. Try this today: in your next conversation, take a deep breath and intentionally slow down. Notice when your mind starts forming responses before they’ve finished speaking. Gently return to simply being with their words. This same practice of quieting the noise helps us recognize our own inner wisdom when we need it most. The gift of your complete attention is precious—both to others and to yourself. #DeepListening #ActiveListening #InnerVoice #BeStill #MindfulConnections #ListenToUnderstand #MentalStillness #PresentMoment #ConsciousConversation #SelfAwareness #MindfulListening #AuthenticConnection #SlowDown #QuietTheMind #ListeningSkills #RelationshipWisdom #EmotionalIntelligence #MindfulCommunication #SoulfulListening #InnerWisdom
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Being Too Understanding? It’s Hurting You! 🥹 There’s a fine line between being compassionate and being a doormat. Learn when empathy goes too far! #lackofboundaries #lackofrespect #peoplepleasing #letthem #mentalhealth #selfawareness #datingadvice
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I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! 

Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them!

Let me know which date idea you try first! 💕

#datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
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I’m so excited 🎉 to share my interview with @thecut alongside Dating Coach, Grace Lee, about summer date ideas! Whether you’re just starting a summer fling or you’ve been with your partner forever, I share tons of ideas that’ll get you out of that boring dinner-and-movie rut. Make sure you check out the article to see all of our recommendations. I think you’re going to love them! Let me know which date idea you try first! 💕 #datingideas #dateideas #firstdates #summerdates #datingadviceformen #datingadvice #creativedateideas
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