Do You Wade in or Jump In???


We dove in! Took a deep breath over and over. Hung our hearts out to dry. Drank enough coffee at those coffee shops to need a teeth whitening…and we prayed, cried, gave up in despair, picked ourselves up, dusted ourselves off… and we met someone who looks just like the picture online and in our minds. Now what?


There’s enough oxytocin flowing to fill a koi pond and when you spend time together, it feels as if time stands still. Eager to know this new person, you begin to ask him/her about life, love, children, work, plans for retirement, favorite foods, whether they want to thrash Donald Trump. The questions help you make some sense out of so much you don’t know.  Our minds want to evaluate, gather data and make judgments. Bless that mind’s heart. It’s working so hard to keep us safe. You gotta love it. And, you gotta watch it.


Meeting someone new that you feel attracted to feels like a miracle. It’s wonderful to finally have someone open a door, put his hand on your back when you cross streets and send you texts and photos of his dog. You want to connect, feel close and connected and one way human beings develop intimacy is through sharing stories.  But how do we know which stories to share and when the right time has arrived for sharing them?


When you meet someone new, remember that discovery takes time. Each person has history and by the time we are over 50, we’ve lived, loved and felt the pain of loss over and over. We are tender and more reticent to open ourselves to being hurt and disappointed yet again. It doesn’t mean we aren’t ready for love, simply that we are human and need to be treated with great tenderness.


I know that urge to want to know everything and to share everything that will help create the intimacy and closeness that I love in relationship, especially for a storyteller like me.  It’s tempting to ask or reveal too much too soon or to ask the new person in my life to share his history before he’s ready.


When you hear yourself sounding like an FBI agent during an interrogation, or you see them looking at their cell phone right smack in the middle of a sentence, it might be a clue to stop and assess. Think of you and that other person as tulips in Spring. All tucked in, closely guarded for a reason…they need time before they are ready to open. Human beings open when they feel safe and ready and not one of us has the same conditions for that to happen. So, better to take it slowly and one step at the time. If it’s a match that has a chance to grow into more, the soil of trust will have been created on which a foundation can be built.

Are you tired of watching sunsets alone, wanting to open up your heart? Ready to do whatever it takes to find someone special to share this next amazing chapter of your life?

 Call me at 510-817-4242 or email me at to schedule a Complimentary Strategy Session. 

Donna Bailey, MS

Coach, Speaker, Writer, and Expert in Dating and Relationships for “Grown-ups”

Donna’s Big Red Chair


Big Red Chair

Dreams are Sexy Things!



What’s life without dreams? Not the kind we have at night, but the ones we have when we’re sitting by a river or watching a movie about India and know we need to go there “one day”.





Some of us have carried our dreams like a suitcase all our lives while others realize late in life, gazing into our bucket where the list is kept, that life is short and the list, long. One of those dreams might be finding someone to love again or for the fortunate, having  found someone so special, they think they might have to give up their dreams to make it work.


In my practice I often see people who don’t open their hearts to love because they think it will mean giving things up. Their belief is that she or he won’t want to (fill in the blanks)…sail on the weekends, travel to Australia, RV across the country. They go it alone because it’s the only choice they feel they have. And then there are those who have been living their dreams, who are vibrant and want more of what life has to offer. They fall in love and whether a partner asks it of them or not, they feel the dream must be relegated to the dust bin so they can “focus on the relationship now”. They sacrifice out of what they see as love, and a little part of them begins to wither.


Dreams, even the musty ones we’ve carried in that suitcase, are the language of the soul. They are a North star to the essence of who we are, what matters, our juice of life. Do you know what both men and women find most attractive about a partner, or even a date? Vibrancy. Aliveness. Curiosity. DREAMS! People who live their lives, act on their dreams or have an intention to fulfill them bring life and excitement to their relationships. But there’s a hitch…when we meet each other or are getting to know each other it’s essential to talk with each other about those dreams. If we’re already living them as writers, musicians, volunteers, artists, change agents, politicians;etc. we want to be sure that our partners know these things are who we are and that they will support us in growing our dreams as life goes on.


You don’t have to stop living the life of your dreams to be in love with another. In fact, we all need someone to share our lives and bring with them dreams of their own. Added to ours, they make for a really juicy life!


Are you a hopeless romantic who’s tired of watching sunsets alone?  Ready to do whatever it takes to find someone to share this next amazing chapter of your life?  I can show you how to navigate the waters and find that dream.


Donna Bailey, MS

Donna’s Big RED Chair

Dating and Relationship Coaching for Grown-ups


Big Red Chair



I Found the Moon Again



I looked at the full moon last night, realizing how incredibly beautiful she is and wondering why I had missed so many of her wonderful displays over the past year.


I turned off my living room lights, standing by the window looking at every detail of her face, remembering how over the years she’d been my solace during times just like these…periods of painful and exciting transition. And I felt the tears sting as they rolled across my cheeks. How could I have not noticed her these past months?  I apologized to her for my forgetting and my heart opened, quite suddenly feeling such deep compassion for myself. It was a hard year.


Those of you who know me personally probably know how much I believe in the power of love. Not only romantic love, but most importantly, self-love. And for most mortals, it’s a lifelong journey, probably the most urgent one we have while on this earth.  It’s never delivered in a pretty package. Our bodies challenge us, we lose faith, the “unexpected” happens and for some mysterious reason we’re always surprised because somebody told us life was easier than it truly is. Life is a slog uphill much of the time. How do we get to the place in our lives where we find a place of peace and love so that each day, no matter what happens is one for which we are truly grateful?


I’d like to give you the simple answer if there were one. I don’t believe all the books, podcasts or even sermons get us to peace of mind, but I do truly believe that each thing we do, person we meet, challenge we take on despite our fears and less than perfect bodies gets us there. The hero’s journey, as Joseph Campbell called it will mean we must be awake and desperately want joy so much that we’re willing to do the work required, knowing that the road will bumpy and winding.


Finding someone to love is exactly the same journey, requiring hard work most of the time and a stubborn willingness to get on the path, heart open and trust there’s someone out there looking for you too. Someone who, if your list of “must haves” doesn’t fill an entire page, can find his/her way to you. You have to want it badly enough to do whatever it takes because  you believe the journey will be worth the work. The first steps are always about loving yourself, feeling compassion for your own journey and finding your way back to the moon.


Are you tired of watching sunsets alone? Wouldn’t it be amazing to be with someone during the full moon? If you’re a hopeless romantic looking for your next amazing love, willing to do whatever it takes, I can show you how to get on the path to find someone to share this next amazing chapter of your life.


Get off the sofa and call me or email me today for a Complimentary Session!

Donna Bailey, MS

Coach, Speaker, Writer and Expert in Dating and Relationships for Grown-ups

Donna’s Big RED Chair



Big Red Chair




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