dating widow

The Awkward Phase – a Widow Dating

You know that awkward teen phase where you’re trying to come to terms with who you are, how you fit in the world, what you want to be when you grow up? That’s me at 62.

I’m a mature woman (well, according to my son, and many of my closest friends, that may not always be true). But, to the rest of the world, I appear to be a mature woman. I’ve been on this earth for sixty-plus years, and I’ve lived a long and somewhat eventful life.  I should be pretty comfortable with who I am. But, as a former happily married woman, turned widow, turned single-woman-dating-eligible men, I’m also in some strange new world, and that’s the awkward part.

I may be a little unsteady in how confident I am approaching the dating scene. One week, I’m talking to a couple of men, and going on a couple of dates, and enjoying the heck out of it. The next two weeks, I need a break from the newness of it all and take a hiatus. (And, yes, it’s true, since I’ve always been a list maker, I do have a chart to keep the men from each dating app straight.)

On the other hand, I am confident in what I want in a man, and I’m plowing through the list with that in mind. I don’t waste time with guys who obviously don’t fit. Rude to the waitress? Gone! Great to your late wife, but you offered a gun to your mom when she was suffering from dementia? Yeah, eHarmony gave us four 100% scores for compatibility, which is more than you’ve ever matched with a woman, but I see a problem with you. Next!

My confidence level rises and falls like a prepubescent boy’s voice. Yes, Rick loved me the way I am, and so far, about a dozen men have said that I look young for my age, so that’s an ego-booster. I was talking on the phone one night with my youngest date so far, a 54-year-old man, and he wanted to switch to Facetime. I said okay, and when our faces popped on screen, he exclaimed, “You’re so young!” I thought that was strange, since he had seen my photos. What did he think? That I had blue hair in a bun? Although I have to admit – it felt great to hear! Flattery will get you everywhere.

But face it, body-wise, I’m a grandma who sits at a computer for a living, trying to avoid carbs, so I’m no Jennifer Lopez. I update my profile pictures every couple of weeks as I lose weight, because God forbid these guys would see how fat I was last week! So, I grin and bear it, and post a full-length honest and current “a little-less-fat” photo every few pounds, so no guy is surprised when we meet. But I was kind of shocked two hours after posting one last week, when I got a message: “Very pretty face and a very lovely figure” with an emoji with stars for eyes. Over the next day, I got twenty more “likes” and “wants to meet yous”! This is bizarro world – but a great confidence-booster! Dating is definitely a roller coaster ride, but I’m hanging on and trying to enjoy it.

So, honestly, despite the whirlwind of emotions that result from entering this new phase of my life, I am having fun. I’m enjoying the ride and the novelty of being wooed again. Being “courted” by men who are trying to impress me (and/or get me into their beds) has been a real trip! When I was single and nearing forty, Rick was my first date since having Brandon in my twenties. My first and last date. So after nearly forty years since being in the dating world, this new lifestyle sometimes has me feeling twenty again. Here I am at sixty coming to terms with all those elusive questions. Who am I today, and what am I looking for in a man? Does this guy fit? Is he a keeper or just a guy to have fun with? Is he a potential for really connecting, or are we only compatible on paper and there’s no chemistry? Do I even want a “Mr. Right”? I’m enjoying my life as it is. I’m living my own life, in my own space, and meeting all these interesting men is actually fun. I don’t think I’m ready for more than that right now.

Feeling like I’m twenty again in my head when I go to bed at night is a strange and somewhat pleasant feeling, but the reality of my age sinks in when my body is stiff from arthritis in the morning from dancing the night before.

And, of course, besides coming to terms with who I am at this age, and who I want to date, or not date, there is that underlying, yet overwhelming sadness when I’m reminded that this is not where I want to be. I look at Rick’s photos on my desk and think, I never would have guessed he wouldn’t be by my side right now, that another man would be kissing me goodnight. True, I no longer identify as much as “his widow,” and I feel like I’ve come into my own again. I don’t feel that sensation that I’m half a person much anymore. I don’t look for him to come in the door, or listen for his voice down the hall, or feel him missing in the bed when I wake up in the morning. No, I’m used to being here on earth without my other half. But I miss the connection I had with him, and still feel an aloneness that I haven’t felt since before we met. Dating all these men just reminds me of who I’d really like to be with, laugh with, kiss, and hold.

I asked my counselor how I will ever stop comparing every man I meet with Rick. She said, you won’t stop. You’ll always compare them with him. Just don’t do it out loud.

So, I keep my mouth shut about my late husband and how much I loved him. I keep my mouth shut about twenty-plus years of my life – or try to. It’s always awkward saying I rehabbed a couple of houses. I didn’t do it. We did. Or I’ve been to forty-some states and parts of Europe. I didn’t go alone to any of those places. Rick took me there. I visited my ancestors’ home in Cornwall. But I didn’t visit alone. Rick and I stayed at a lovely cottage and walked on the moors together – my dream since I was a young girl.  Two decades of my life weren’t a solo ride. I experienced it all with a man I loved dearly. A man I still miss terribly. A man who should still be here by my side.

I’ll admit, it was toughest on the first date, not mentioning Rick, not saying “we,” but it’s gotten easier now. It’s also a little easier when I date a widower, because he definitely gets it and we share stories about our marriages. But, honestly, a never-married or divorced man who doesn’t at least understand that there was a man in my past whom I will always love isn’t the guy for me, anyway.

So, I meet men and I enjoy and/or endure the ups and downs of the dating scene. I go on with my life. I’m having fun. I’m alive. I’m thriving. I’m a 62-year old single woman who can choose to go anywhere I want, with anyone I want, and after two years of grieving, I’m finally enjoying this world again. I have some great conversations with guys, some late night chats that are so interesting I don’t want to hang up, and some awkward dates where I can’t wait for it to end. I date some very nice men, and some not-so-nice guys. Some dates are fantastic and last for 3-4 hours, and others, not so great.

But after every date, when I come home, I talk over the experience with my husband, who’s waiting for me out under the gazebo. I tell him what I liked and didn’t, how I feel about the date and the man, and then…I tell Rick how much I miss him. I listen for his voice in my head telling me his take on the situation, because he was there with me, and he knows me better than anyone else in this world. And I hear him telling me that he will always love me, but it’s time for me so start living and loving again. I know he’s happy for me. He’s proud of me. The man who loved me more than anyone ever has would be disappointed if I spent the rest of my life pretending he’s still here, shut up in our house, caught up in our memories, living in the past in my head.

After some dates, I can even hear him laughing that deep throaty laugh and telling me, “That guy’s a jerk. Cut him off. You deserve better.” And I know in my heart that he’s right, because once upon a time I was loved utterly and completely by a wonderful man who respected me for who I was and wanted the best for my life.  The bar has been set pretty high this time around in the dating world.

So, yup, I guess you could say, I’m definitely in an awkward phase, starting a new life as a single woman, dating in my sixties after loving and losing the man of my dreams.  But as I keep moving forward, I’m sure I’ll eventually figure it all out – and I’m having a blast trying!

About the author

Katherine Billings Palmer is a technical writer, poet, and essayist from Garden City, Michigan. She’s won several academic writing awards, including first place in the University of Michigan Dearborn Critical Essay Contest for her work about poet John Donne: “‘The Sun Rising’: A Lover’s Boast.”

In 2017, Katherine’s husband, Rick, died of complications from small cell lung cancer. She wrote a series of poems and essays about her struggles to cope with her grief. I Wanted to Grow Old With You is available on Amazon in paperback and Kindle editions.

Her latest book, A Widow’s Words: Grief, Reflection, Prose, and Poetry – The First Year was published in January 2019 and is also available on

Katherine is a guest blogger for the Hope for Widows Foundation and writes about her grief journey at

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