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  • Writer's pictureCarolyn Moor

Love is a Risk Worth Taking

Updated: Aug 13, 2022

As a mentor at Modern Widows Club, I often share stories of my own experiences at our Social Hour gatherings, online or my personal mentoring sessions. Over the years, I’ve been able to give a VOICE to Modern Widows by first finding my own.

Nothing has brought my personal voice out higher or wider than opening my broken, albeit mended heart to the potential of a new relationship. Hands down, the number one hottest topic in mentoring is invariably the big step into the dating world again and the potential of new relationships!

Because not only is it the number one core desire for many, it’s the number one fear also.

And with good reason. Fear and desire feels like oil and water, the two do not mix well unless disturbance happens. Right? In fact, the two can co-exist if shaken up enough to become one and I’ll share with you what the experts are saying about that commotion later in this talk.

Hey, let’s look at this time in our life as a perfect storm headed for a silver lining.

As widows, we are risk-averse, aren’t we? Dating again after becoming widowed is a touchy, emotional subject and yet worthy of deep consideration for many positive, practical and life giving reasons.

A while back, I led by example and took some of my own medicine. After all, I was encouraging my mentoring clients towards this endeavor. After ending my last relationship a few years ago, I took the time to understand what happened between us and was ready to move forward. So, it was time for me to ‘put myself out there’. I signed up for not one, but two online dating sites. OMG.

OK Cupid and eHarmony. I approached both with the intention of putting my best foot forward and a genuine intention to be open to possibility.

Well, the first face to face date went well, but by the third date, he forgot his wallet and it left me very unimpressed, it spiraled downward quickly.

The second face to face date went much better, he flew 850 miles for a 4 hr brunch, then back home in a day. Promising - I thought, especially since he kissed me at the airport, but the next morning I received a text saying he adored me, BUT not sure he felt the romantic spark. Agreed. Then he asked to be friends. I declined.

What’s a woman to do? We just can’t predict what will happen. And worse, we have to accept this environment is on shaky ground. However, we don’t have to accept that WE are shaky ground though.

I never returned to dating sites ever again, and I’m very solid with making that decision. It wasn't for me. Aside from the increased predation that widows experience, I found I meet people naturally in areas of interest that I'm already passionate about. Architecture, interior design, vintage cars, travel, music, baseball, holistic health, gardening and advocacy.

Here is the thing. In the past, I was blessed with a loving, stable, desirable relationship with my late husband where I was his cherished equal. I’m armed with this life experience and knowledge which might be preventing me from finding a loving partner again in my life because I know what a true love relationship looks and acts like.

And yet, you see, I fully suspect my next relationship will be the BEST I’ve ever known!

I do (no pun intended).

Why? Because this new relationship will bring all of ME right up until this point in history as we find each other ‘and suddenly’ begins to begin. And let me tell you, God has been doing some deep work on me….and I suspect on him too for years! That’s why it's taking so long. (This is why patience really is a VIRTUE!)

This new relationship will be complete with its own unique joys, adventures, struggles, risks, excitements, conversations and desires. So why do I think it will be the best?

Because of everything I’m about to share with you here that I have learned while rebuilding my new me identity in widowhood.

Let me first comfort you by saying, many, many widows before you have approached this risk- taking transition wholeheartedly and surviving. And many, many have also thrived whether that ended up in a relationship or not.

In the end, they turned out to love themselves just a bit deeper, in amazing new ways. All worth it.

  • Love is a risk.

Many years ago, I was honored to be a part of the new OWN Network show airing called Help Desk. The concept was visionary leaders answer a multitude of questions in a public setting. The show I was selected for was in located in Hermosa Beach, CA with Time’s Top 100 Most Influential People Pastor Rob Bell.

Of course, my burning question was about love and remarriage again in widowhood (always a voice for Modern Widows). My question was

"Is it possible to feel whole again without remarriage?"

Although, I can't remember his complete, long winded answer, the bottom line of his advice was “Love is a RISK. A risk worth taking”. He added one caveat at the end saying, "The struggle will be finding someone willing to take the same amount of risk as you."

Got it.

  • New Eyes are Required

Moving forward we look outward and look inward with new eyes. This leap of faith will have you looking insanely directly into the mirror at yo’ self. New eyes are required, not optional. Not the rose colored eyes in the troughs of the grieving process, but the clean slate eyes of future dreams. Eyes that are virtuous; patient and full of grace and a sense of humor towards yourself and your future partner.

You know the saying ‘The eyes are the windows to the soul’. It’s true. Reach deep down into your soul and begin to discover what it’s saying to you about living a life open to the positivity of love.

Those eyes can’t hide the sparkle or the lack of.

This life of loss is an opportunity to renew and reinvent like never before. With new eyes, you can face this holistically.

I like to repeat this quote from Zen Master Shunryu Suzuki

"In the beginner's mind there are many possibilities, but in the expert's there are few”.

See yourself as a beginner, not someone who is defeated or carrying baggage or anything from your past. This is a fresh new beginning if you will see it that way. See it as magical.

  • Go Go Boots and Balls

Going on dates will be more fun if you bring your Go Go Boots (Cowboy Boots and thigh-high boots are good too!) and Balls. Meaning, if you are a woman, bring the feminine, sensual, lightness and fun, but don’t forget your pioneer, flaming Katniss spirit. ‘These boots were made for walking’ is about confidence, feminine divinity, sacred sensuality and taking a calculated risk while collecting data about you, them and your potential togetherness.

If you are a man, bring the masculine manhood and joy. Be a ‘I Got This’ kind of man, chivalry and mystery are not lost on us Thor. Take a minute and remember your playful, heroic child’s heart, before all the pain and assumptions come seeping into your life, then GO GO anyway on that date. A little imagination of having ‘go go boots and balls’ will take you a long way.

  • Don’t Worry Be Happy

Humans want sexual healing, affection and desire. We aren’t adults coming together to play fiddlesticks.

We long for companionship, intimacy, security and connection. Widows miss the space in which sex and intimacy once reigned in their relationships. Yep, I went there and I said it.

Guess what people? Your next partner wants you to show up as a real live woman or man…. not as a widow or widower. I figured ‘this part’ out all on my own after many craaaash and burn experiences and seriously awkward mishaps!! Live and learn.

Kissing Frogs? Oh, please, I wouldn’t even know where to begin to unearth the many amphibian adventures of finding frogs in widowhood dating. But I found the theoretical proof of why we go searching for frogs to kiss in the book Arousal by psychoanalyst Michael Bader. He explains that with intimacy comes a growing concern for the well-being of the other person, which includes a fear of hurting the other. (Damn, there is fear everywhere- their side, our side). Kissing frogs is just about facing fear of rejection and making choices to just do your best. Do your best, even if they are a frog.

Special note: Sexual excitement requires the capacity to not worry, and the pursuit of pleasure will demand some level of selfishness. Ouch! I guess that song ‘Don’t Worry be Happy’ was right all along! Any kind of ‘sense of burden’ is a buzzkill moving towards a new relationship.

Just be aware of this concept. Ok.

  • No Judgment Zone

In the eyes of many, a person who is struggling with the heaviness of grief and loss, is not ready for the spontaneous, sexually alive and carefree approach required to be searching for a new mate. (Duh!) And yet, on the other hand, we have needs that absolutely say ‘GO’. You know what I mean Hugh Jackman fans.

As shocked as you will be when it arrives, we run the risk of not only engaging in desire too quickly, but more importantly, lacking the erotic fortitude to sustain the union in a healthy manner which could create a pattern of another round of losses we are ill equipped to handle. So, what does all this mean?

It means we need to do our damndest to not judge others or ourselves too harshly because we are all simply doing the very best we can in these human bodies and minds. Spiritual beings trapped in a physical body. What was God thinking?

Date when it feels right for you. Leave the guilt and shame near the door. No one does life perfectly, and no one does widowhood perfectly either.

So, now you know love is a risk worth taking, it requires new eyes moving forward, taking along some go go boots and balls to get you through to a space where you will be singing ‘Don’t worry, be happy’, all the while ushering a judgment free zone for something new in your dating life to flourish.

Slowly, but surely your core desires will be met. It's sure to create some interesting stories to share with your friends.

But wait a minute, what about fear? Oh, yeah...that little thang. I’ll talk about that more next time. In my post “Facing the FEAR of Opening Your Heart Again”

Until then, share some of your stories of dating in widowhood in the comments below. We are all here to learn to love and love life again renewed. Imperfectly.

To Love Renewed and Honored,

Carolyn Moor

P.S. Modern Widows Club has a popular Dating Club now. Sign up here.

Learn from other widows facing the dating world or share your expertise with others who welcome it.

I wanted to share TWO Videos:

1. At Modern Widows Club, a few years back we asked our widows "How do you feel about the possibility of dating again?" and they spoke from the heart.

2. Watch this video about "MWC Origin Story: Starting with 7 Widow Advocates Who are All Remarried" and today, are giving back in their own unique way.


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