Ask Coco

“Coco” is a pseudonym for Thrive Correspondent Colleen Cook, a full-time working mom and wife in her mid-30s who has career experience as a business leader and marketing expert. Think of her like the big sister you can lean on for your medium-sized problems.

For this week’s “Ask Coco,” two questions came in that were destined to be coupled: 

Dear Coco,

I'm widowed. I'm not too old to start over with someone, but it's been many years since I have been on a date. I'm afraid to ask a friend or someone at work or church because those can lead to problems. Any ideas? 

— Lonely 

Dear Coco,

How does a single senior lady meet a good single male? And to even know what to talk about? It’s scary for me. I don't know how to date anymore. 

— Senior Single 

Dear Lonely & Senior Single,

Our souls were created for connection. We’re meant to share our lives with others, and inherent in that is the certainty that, someday, it will come to an end as all things do. Yet, in long, good seasons it can be easy to let those relational muscles atrophy, fostering and nurturing our committed connections rather than forming new connections. 

Clearly, you’re not alone in this struggle. So much of our identities are built upon who we associate ourselves with most closely: our partners, our children, our families, our closest friends, our colleagues. The end of any of those relationships can leave us disoriented and uncertain of how to proceed.

I remind you of all of this because, inherent in pursuing a new relationship is the knowledge that all beginnings have their ends, and ends are painful. You’ve lived long enough to know that pain, you can’t walk into the next relationship with the naivete we all enjoyed in our youth. As you begin, it’s important to make peace with the certainty that there will be pain along the way rather than fear the inevitable. 

In coming to terms with the wisdom that experience has taught you, you’ll free yourself to take risks and be vulnerable, because you also know now that with great risk comes the possibility of great reward. Proceed boldly, my friends! There is so much to gain!

If you’re struggling to meet people, seek out some ways to network: volunteer for a cause, take a class, join a group, start a hobby. Don’t be afraid of dating apps, they’ve come a long way and many people find like-minded connections by taking advantage of what this technology has to offer.

Know that the foundation of friendship is rich soil in which to grow a relationship, so don’t shy away from your circle of friends, if they’re available. Sure, there’s the risk of messing something up, but there’s also the possibility for something far better than you’ve ever known. 

People form bonds around shared experiences and open hearts. Tell your stories and ask them theirs. Don’t hold back, and don’t hide. Truly listen to the other person, and stay curious. You stand only to gain from being your true, authentic self. Remember, the person you’re sitting across from wants to connect with someone as much as you do, so don’t try to impress them, try to know them. 

You still deserve to be known and seen and to experience the joy of true connection with another person. Don’t be afraid to try and fail, my friends. Sure, there will be pain, but there will also be joy and the richest experiences in life. And, please let me know if you each would like to connect with the other writer… it could be destiny at work. 

— Coco 



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Colleen Cook works full-time as the Director of Operations at Vinyl Marketing in Ashland, where she resides with her husband Mike and three young daughters. She's an insatiable extrovert who enjoys finding reasons to gather people.