How Do You Date After Loss? 

In Advice and Encouragement, Dating, Mental and Emotional Health, Podcast, Relationships by Debra Fileta2 Comments

How do date after the deep loss of a marriage? Is it possible to love again?

Today I talk with Diane who is a widow that is trying to heal her heart after the death of her husband. She’s having a hard time navigating the dating world now that she’s single in her 60s, yet hasn’t dated since her 20s!!

We talk about her grief and how to heal, and when to know you’re ready to date!

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DEBRA FILETA is a Licensed Professional Counselor, national speaker, bestselling author, relationship expert, and founder of the Debra Fileta Counselors Network. She’s written six books including Choosing Marriage,True Love Dates, Love In Every Season,Are You Really OK?, Married Sexand RESET. She’s also the host of Talk To Me: The Debra Fileta Podcast (formerly the Love + Relationships Podcast) where she facilitates on-air authentic counseling-style sessions. Her popular relationship advice blog,, reaches millions of people with the message of healthy relationships. Connect with her on FacebookInstagram, or Twitter or book an online session with her or someone from her team today!


  1. Thank you for tackling this question. I am 66 yr old widow of 3 yrs and struggling with the idea of needing to date in order to get to a place of a healthy, fruitful, fulfilling Christian marriage that I desire to have but scared of the dating process to get there. Thank you for bringing up all the emotions, that bubble up to the surface after a loss and that I’m not weird, weak or overly emotional that it’s happened and that it’s normal and healthy and needs processing . It is the work that I’ve been doing and I finally feel ready to at least start this process which is very scary but very necessary to get to a place of having my dream of a thriving marriage. Thank you for bringing up the differences of needs and foundational things that are important versus preferences. There definitely is a difference heading into dating as an older adult with 40+ years of experience and seems like it would be harder to find someone with so much knowledge of what you will and will not tolerate, but at the same time an ability to not waste time and with God‘s help find that right person …that needle in a haystack …so please pray for me . Any relationship advice or any special advice you could give to me would be great and I did buy your book reset and just started it last night so prayerfully heading this direction !!! I’m trying to keep a positive mindset, but it’s still scary!!

  2. This was a very relatable session. I was married for 48 years, and my wife passed away 5 years ago. I tried to date after 2 years and when she said no, I wasn’t upset as much as I was relieved. That’s when I realized I needed to work on healing before I started a new relationship. I’m still building my “new normal,” a phrase I hate, but it’s a reality.
    I continue to meet with this woman (in church and for breakfast) and we agreed to a very platonic relationship. She is a widow and a strong woman of faith and we try to help and support each other.
    While I would consider a relationship with someone, I don’t need one. I prayed for a relationship early on but have altered my prayers to “If You have someone for me, show me but give me peace in my singleness if that is Your plan.”

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