Is It Them-or You? 5 Signs You Might Be Struggling to Date
Dating today can feel exhausting! One minute it’s fun, the next-completely overwhelming. Most of us are on a mission to find “the perfect one,” though I’m still figuring out exactly what that means when clients bring it up.
If you’ve ever found yourself asking, “Why does dating feel so hard?”-you’re not alone. It is hard! And it’s rarely just one person’s fault. There are so many factors to consider. Are we trauma bonding? Do we have different attachment styles? Are we even compatible?
With so many unknowns, dating can feel draining-so much so that a lot of people want to give up.
Let’s go over 5 common signs I’ve noticed people struggle with when it comes to dating, and what you can do to shift the experience.
1. You Keep Attracting the Same Kind of Person
Understanding your attachment style is key. It reveals how you show up in relationships-and who you're most likely to attract. Learning how to build a secure attachment style will help you start attracting healthier, more emotionally available people.
Example:
People with an anxious attachment style are often drawn to those with an avoidant style. If you’re the anxious one, you're more likely to chase someone who shuts down emotionally.
What to explore:
Work with a therapist to help you develop a more secure attachment style before diving deep into dating. It makes a big difference.
2. Overthinking Leads to Disappointment
Do you find yourself replaying conversations, worrying what others think, or fearing rejection?
What to explore:
Shift your mindset. Not everyone will hurt or abandon you. If you’ve been burned in the past, it’s normal to build emotional walls, but starting fresh means giving new people a fair chance.
Psychological generalization (assuming everyone is like your ex) only keeps you stuck in old pain.
3. You Struggle to Be Vulnerable
Avoiding emotional intimacy or keeping conversations surface-level blocks meaningful connection. You might fear being vulnerable because past experiences didn’t feel emotionally safe.
What to explore:
Set healthy boundaries for how much you're willing to share early on, but remember, building rapport requires openness. Vulnerability isn’t weakness, it’s how connection grows.
4. You’re Not Sure What You Want
Are you looking for a committed partner? Are you unsure about dating someone with children? Whatever you feel-it's valid.
What to explore:
Clarify your values. Ask yourself: What are four non-negotiables I need in a partner?
If someone doesn’t align with those on the first date, it’s okay to move on.
5. You Self-Sabotage When Things Go Well
This might be the biggest one. You meet someone great… and suddenly, you lose interest, find flaws, or assume the worst.
What to explore:
Identify your red flags and don’t let fear drive assumptions. Learn to give people the benefit of the doubt and allow the relationship space to grow. It may feel uncomfortable at first, but that’s okay.
Therapist’s Orders: You’re Not Broken
Struggling to find the right person doesn’t mean something is wrong with you. It may mean you're still healing from old wounds. I always remind my clients that self-awareness is the first step to change.
Understanding your attachment style, relationship patterns, and emotional needs can transform the way you date. The more you nurture your relationship with yourself, the stronger your relationships with others will become.
