Don’t Ask Unless You Really Want to Know


We treat it like it weighs nothing, and only when the answer is not what we expected do we realize the gravity of it. Southern folk say, “Hi’re you?” and like the rest of us, all we really expect to hear is, “Fine”. And what exactly does that word really tell us?


Maybe it’s just me, but I’m forever getting a text, “How are you?” and most days, I have no idea how to respond. I feel so many things in the course of a day, so I guess I am supposed to kinda give a summary, like a Cliff’s Notes
version of the truthful answer? And, if I’m frozen in sadness, anxiety or overwhelm I wonder if they really want me to be honest or say, “OK”…which is a very open-ended word that means absolutely nothing.


How many times when someone asks you how you are, have you wanted to really tell them the God-awful true answer…”I’m really crappy,”  or “I’m a hot mess.” but you don’t know if they’re ready to hear what life is really feeling like at that moment? So, you hedge your bet that they didn’t really mean it, and say, “Fine”.


We all long to be heard, to have our feelings honored for the beautiful, complex, confusing things they are. Research has shown that human beings want nothing more than to be heard, valued and accepted. We want to tell each other the truthful answer, but it can’t fit into a Tweet or a square box that uses up a data plan.


And what will you do if you’re not prepared for an honest answer or you don’t have time to listen to the words waiting inside Pandora’s box?


The next time you text someone that generic, “How are you?”, stop and think about it. If you really want to know, be sure you have the time to really listen. Wait until you know you can honor what they might want to tell you, and up the odds that they’ll tell you the truth if you just pick up the phone so they can hear your sweet welcomed voice truly wanting the answer.


Perhaps we also need an internationally recognized scale with which to answer…1 is “I’m standing on the ledge right now”_______________________________10 says “Nirvana, baby, Nirvana.” And maybe 5 is really the true meaning of the word…”Fine”.

Donna Bailey, MS

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

Donna’s Big RED Chair


You Got Yours…I Got Mine




“Maybe you and I were never meant to be complete
Could we just be broken together?
If you can bring your shattered dreams and I’ll bring mine
Could healing still be spoken and save us?
The only way we’ll last forever is broken together”

Excerpted from “Broken Together” performed by Casting Crowns


Most of my life I thought there was a man out there who was better than the one that was in my life.

Someone with a mother who hadn’t criticized and judged him , a father who loved him just the way he was, a man who still believed in love and who could show up with everything necessary for a healthy and happy relationship. Is it too much to ask??


Years passed, my relationships began blissfully and ended sadly and still I believed that Mr. Close to Perfect just hadn’t appeared yet. Maybe he would be in the next round of “Matches for This Week”.


It takes as long as it takes to learn something, but thank God I finally got it! Everybody that has lived as long as I have is battered and bruised and comes with an array of gashes, scars and a few gaping holes in their souls. And guess who’s among them?


Often people who are single say they are looking for a healthy partner with no baggage. Most want to begin with a clean slate, but it isn’t gonna happen. We are all like famous paintings hanging in the Louvre, each of us with layer upon layer of old “paint”, the product of countless ” failed”attempts. 


Successful relationships are possible and well worth the courage it takes. We grow them only when the soil is forgiving and the gardener is compassionate. Before we can expect someone to love us as flawed imperfect people, we MUST learn to love and accept our own imperfection.


Don’t get me wrong. There are many people who are unable to create and sustain healthy, functional relationships. And there are people who are toxic and unhealthy for us. No amount of love can change them. A therapist, maybe. It’s the man or woman that has the health and humility to see their part in past relationships that didn’t work, can see the need for changing something in themselves so that they get different results, and most of all a DEEP DESIRE to do the work it takes together with a partner who wants that very same thing….a loving, nurturing relationship with a foundation of trust and the guts to stay when the urge to run feels like a case of poison ivy.


Stop looking for perfection in a partner. If you are one of the lucky ones and find a special someone with whom you want to share precious time on this Earth, cultivate compassion and summon the courage to dig deep to make it work.

Does this sound like something you’ve done and maybe are still doing in your search for love? If you’re ready to do the work to get rid of this roadblock so that you can find someone to share the next fabulous chapter of your life…Call me at 510-817-4242 and let’s do a Strategy Session together so that next time this year, you’re happy looking in that mirror!

Donna Bailey, MS

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

Donna’s Big RED Chair   510-817-4242

Why Are the Boomers Ageist When Looking for Love?




Many people over 55 and using an online site to meet someone continue to post photos of themselves when they were 5-15 years younger and then wonder why people get upset when they show up for that cup of coffee or a martini to find, perhaps a still handsome or beautiful person smiling at them, but not the younger face they were struck by on that dating site.

People I coach want to justify that it isn’t really lying, arguing that it is necessary if they are going  to ever meet someone. “Nobody wants to date a man who is 70.” “I don’t want to be pushing a wheelchair in a year.” “If I put my true age in that profile, nobody contacts me.”   What’s really sad about these statements is that many times, they are true. So what ‘s the deal?

I think the reasons are complex, convoluted, and unconscious much of the time. But it’s time to begin exploring ageism among those of us who have heretofore blamed younger generations for it. Until we can understand our own ageist beliefs and perhaps pull our long and more wrinkled necks out of the sand, we are much less likely to find love.

Boomers are great! We are courageous innovators, fiercely independent, passionate thinkers and doers who, by the way, are never going to die. Not only are we never leaving this world until we make it perfect, our youthful spirit is determined not ever to sit down in a rocking chair. That’s why we refuse to see ourselves as ageing in any way shape or form. Those fortunate (or sometimes not) enough to have a good plastics guy can stay in denial longer, but beneath that smooth skin, life goes on.

So, is it any wonder that when we look in the mirror in the morning, we simply cannot see the wrinkles or realize that walking and hiking takes more energy, or that we hate to admit traveling gets more difficult as time passes?

Maybe we all have to post photos of ourselves as younger than we are to get past our own generation’s denial. Perhaps it’s just a little white lie that we make up for when, in our profile wayyyyyy down at the bottom, we say “By the way, I’m not really ______.” The harsh reality is that as we get older, the rules change about getting into relationships. One person, or maybe both, are statistically likely to get sick and die in fewer years than before. “For better or worse” becomes reality. So, with eyes wide open (as open as we can get them now), treasure the years you have and if you want to spend them with another person, show up as yourself and allow others to do the same. If when you look at that photo and know it doesn’t match their age, smile and remember the person who shows up in the coffee shop is the same man or woman in the picture, perhaps with a few more years of wisdom and life experience that might be just what you want in a perfect partner.

Trust me…there’s great love to be had and to be MADE after 55!

If you’re tired of watching sunsets alone and ready to do whatever it takes to find someone to share this next amazing chapter of your life, I can tell you how.

Email me at to schedule a  time to talk about my 90-Day’s to Love 

Donna Bailey, MS

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

Donna’s Big Red Chair


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