5 Tips On Dating In The Midst Of Grief


“So how many brothers and sisters do you have?”

I picked up my glass of water and stared at my date. It was such a simple, harmless question, but what he didn’t realize is that I didn’t have a simple answer. After a painstakingly long pause, I blurted out an answer I knew would damper the mood on our first date.

“Well, I had one brother, but he passed away a few years ago at the age of 13.”

Awkward pause.

This wasn’t the first time the death of my brother brought down a casual dinner date. While most serious relationships I’ve had have not been negatively affected by the loss I still carry with me every day, I fear that possible relationships have been quelled by this unexpected disclosure.

Any loss you experience plays into your dating life. Factors such as age and the relationship you had with the person you lost will shape your grief journey and ultimately how you approach the dating game. As someone who has personally experienced a significant loss, here are my recommendations for navigating the dating scene through any phase in your grief journey:


1.  Don’t be afraid to share your grief

Your grief is a piece of who you are. You have the right to determine who you share this piece of yourself with, but don’t be afraid to open up to someone who you care about and see a future with.

One of the greatest joys of a relationship is knowing your significant other on an intimate level. Without sharing any details of your loss, you place an unnecessary barrier in front of your heart. Decide what you want to share and then go for it.


2.  Don’t trivialize your loss

Just because your date or significant other didn’t know you at the time of your loss or hasn’t experienced a similar situation, doesn’t mean you should negate the impact your loss had on your life. If he or she asks about your loss or grief journey, answer the questions honestly. Don’t say you’re over the loss or that it’s not important because it happened years ago. Your loss is important because it happened to you, and anyone who thinks any otherwise should not be in your life.


3.  Don’t expect your significant other to understand

If you’re comfortable opening up to your significant other about the person who died, it’s fair to expect your significant other to offer a listening ear, comforting words and a shoulder to cry on.

But it’s unfair to expect the other person to fully understand the depth of your feelings or how the loss plays into your life. Grief is unique to each person, so your significant other may not realize what memories are especially emotional or what comments hurt your feelings. Recognize that he or she has not experienced your loss and that their level of support can only go so far.


4.  Don’t search for a replacement

Any loss leaves a hole in your life, some larger than others. The person you lost was one-of-a-kind and irreplaceable, which is why grief is such a burden. You will never find a replacement for the person you lost, so don’t expect the person you’re dating to fill a void in your life.

It’s unhealthy and unrealistic to assume a significant other will fill the shoes of another person, and you will place an unnecessary pressure on the other person with such a high demand. See your new relationship as just that: new.


5.  Don’t let your grief define you

While your loss is a piece of who you are, it is not you. Grief does not define you, so don’t let a difficult time in your life hinder your future.

Honor the person you have lost by living your life fully, while never undermining the importance of grief work. Grief is difficult, emotionally-draining work, but you can bring what you have learned during your grief journey into your new relationship. Great things can result from great hardship, which will make you a stronger, more resilient individual.


Remember, your grief journey is not about getting over your loss – it’s about learning to live your life within that loss. Lean on the Holy Spirit’s guidance as you re-enter the dating scene. You’ll know if you’re not ready to date or if you’re not ready to share details about your loss with the person you’re seeing.

Trust your instincts, believe in yourself and remember that everyone, at some point in their life, will lose someone important.

You will honor your loved one’s life by taking the memories you shared forward with you in the days and years to come.


Editor’s note: The impetus for this post was a recent thread in the Sts. Stephen & Paul forum for widows and widower. “How do you handle the loneliness and onslaught of memories that besiege you?” asked Angela-707424.



  1. Kaye-1256895 October 15, 2015 Reply

    I liked this also. Very helpful and reasonable. What good words “learning to live your life within the loss”. I have referred to it as trying to find my “new life”. Perhaps it could be worded as “learning to live my new life within the loss”.

  2. Gregory-1006607 September 19, 2013 Reply

    I like what was posted. It seems reasonable and helpful.

  3. Elizabeth-613813 April 29, 2011 Reply

    Great story idea! I know just who to send this to!

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