In this personal episode, I take you behind the scenes of a recent dating experience that stirred up both growth and grief — and revealed just how far I’ve come on my attachment healing journey.

As someone who used to operate from a fearful avoidant (leaning anxious) attachment style, I now move through dating with much more self-trust, clarity, and compassion. But that doesn’t mean the old patterns don’t still surface — especially when connection, chemistry, and unmet needs collide.

I’ll walk you through how I navigated this dynamic from a secure place, the conversations I had, and ultimately, how I honored myself enough to walk away when alignment wasn’t there — even when it felt good in the moment.

If you’ve ever struggled to balance attraction with long-term compatibility, or felt pulled between your heart and your values, this episode is for you.

Takeaways include:

• The difference between chemistry and compatibility

• How to identify your unmet needs in real time

• Why even "kind and available" people might not be the right fit

• What it looks like to actually date from your secure self

• How to exit with integrity when your paths don’t align

🎧 Plus: Only 2 more days to join the My Secure Self Membership for just $1 your first month! Get access to group coaching, monthly workshops, and tools to help you build secure, aligned relationships HERE.

Looking for 1:1 support, learn more about attachment coaching here.

Today on the podcast, we’re joined by the lovely Meghan Gatto.

Meghan went through the My Secure Self group coaching program this past summer with the goal of deepening her understanding of anxious attachment — and learning practical tools to break unhealthy relationship patterns.

In this episode, we dive into:

• ​Breaking the cycle of anxious attachment
• ​Attraction to avoidant partners—and how to stop that
• ​How your body signals when you’re in the wrong relationship
• ​Approaching dating from a secure lens
• ​Knowing your needs, raising your standards, and setting boundaries
• ​And we finish off with my signature Secure Self visualization to help you shift from anxious to secure attachment

My Secure Self Membership - Join for $1 today 🎉 

1:1 Attachment Coaching

Today, I’m excited to introduce Joe Reilly, an incredible human and former coaching client of mine, who has been actively working to break his anxious attachment patterns and step into his secure self. We dive into:

• The challenges of anxious attachment
• His pattern of dating avoidant partners and where that inclination comes from
• Healing through a recent breakup
• Learning to be okay with being alone
• How he’s been building a secure relationship with himself through this season so that he can be more intentional about his next partner, rather than make decisions from a place of scarcity or insecurity.

If you’re looking for a heartfelt conversation about attachment, healing, and self-growth, this episode is for you.

Contact Joe Reilly:

 www.joereilly.org

Instagram: @joereillymusic

Attachment Coaching with Jessica:

1-1 Attachment Coaching (8-weeks)

My Secure Self E-Course

If you’ve been listening to the podcast for a while, you know I love exploring how attachment styles impact all areas of life—not just relationships with people. Through my own healing work, I’ve noticed that as I became more secure and confident within myself, that same transformation began to reflect in my relationship with everything—including money!

That’s why I invited Shamina Taylor, a former attorney turned Wealth Consciousness Mentor and author of the Amazon #1 Best Seller Unlocking The Quantum Woman, to share her expertise on:

• How attachment styles influence our relationship with money
• The importance of wealth consciousness
• Understanding masculine and feminine energy in making money
• How a scarcity mindset—whether with people or money—keeps us stuck in insecure attachment patterns
• Practical tips to shift your attachment to money and open yourself to more abundance

Find Shamina:

Daily CEO Money Making Moves

www.shaminataylor.com

Instagram: @shaminataylor

Podcast: Unapologetically Rich

Attachment Coaching with Jessica:

1-1 Attachment Coaching (8-weeks)

My Secure Self E-Course

In this episode, I explore the difference between commitment and compatibility, sharing my personal experience navigating these challenges in a past relationship. I also discuss how to recognize the distinction, helping you better assess whether you’re in the right relationship.

Learn about attachment coaching with me here.

Today on the podcast, I'm joined by dating coach Sabrina Zohar—best known for her transformative podcast, The Sabrina Zohar Show. She brings a no-nonsense, straightforward approach to relationship advice.

In this episode, we discuss:

• Sabrina’s journey from anxious to secure attachment.
• The reality of managing anxiety—it doesn’t just disappear.
• The power of nervous system regulation for those with anxious attachment.
• How to spot emotional unavailability in dating.
• Low-effort vs. high-effort behaviors in dating & relationships.
• Key qualities to look for in a secure partnership.

Tune in for insightful and actionable advice on building healthier relationships!

Contact Sabrina Zohar:

www.sabrinazohar.com

Instagram: @thesabrinazoharshow

Podcast: The Sabrina Zohar Show

TikTok: Sabrina.zohar

Youtube: Sabrina Zohar

Work With Jessica:

1:1 Attachment Coaching with Jessica HERE

My Secure Self E-Course (Self-Study)

Instagram: @thejessicadasilva

Today on the podcast we have Melina Charis. She is a writer and mentor for women moving through grief and heartbreak. She has 10+ years experience with ceremonial + somatic healing practices and 6+ years experience holding space for others, but her greatest teachers by far have been motherhood, death, grief and life itself.

We cover:

• Grieving breakups, death, identity shifts, and more.
• How unprocessed grief manifests in daily life.
• The ways grief can resurface years later.
• Understanding that grief is an ongoing process.
• What it truly means to process grief.
• Different healing approaches and ways to move through grief.

*Find Melina’s offerings at melinacharis.com and read her writing at [/14b27051b990809ab0a4e21d62ab80a3?pvs=25]melinacharis.substack.com.

*Learn about attachment Coaching with JessicaHERE.

If you've been following my breakup journey, I wanted to share an update on my healing process now that it's been 1 year. My hope is that this gives you insight into the grief cycle, the messiness of healing, and reassurance that things do get better.

Work With Me : Attachment Coaching - ⁠CLICK HERE⁠

Previous recorded break-up updates:

- Recovering From Heartbreak - 8 Month Update (Through a Secure Lens)

- Recovering From Heartbreak - (Through a Secure Lens) Almost 6 Month Update

-To Stay or Breakup - Leaving My Relationship of 6 Years

In today’s episode, former client and dismissive avoidant attacher Randy Hamama shares his journey of navigating insecurities in a new relationship. He discusses common avoidant struggles, such as discerning fears from authentic desires, staying present when the urge to withdraw arises, identifying what makes a partner feel safe for avoidants, and understanding when it’s worth staying with an avoidant partner or when it’s time to walk away.

Whether you have an avoidant attachment style or are in a relationship with someone who does, this conversation offers valuable insights and practical takeaways.

Learn about attachment coaching with Jessica here.

Today on the podcast, Vanessa Scaringi, PhD, CEDS-C, a licensed psychologist and certified eating disorder specialist supervisor, and Kathryn Garland, LCSW-S, CEDS-C, a clinical social worker and certified eating disorder specialist supervisor, discuss:

Vanessa and both co-own a group practice Calm Counseling in Austin Texas that specializes in the treatment of disordered eating and body image issues. 

Contact Vanessa and Kathryn:

www.keepcalmtx.com

Instagram: @calmcounselingatx

Work with Jessica:

www.jessicadasilvacoaching.com

Instagram: @thejessicadasilvacoaching