I’m dating again (so are my mom & kids!)

datinggame“You did WHAT?”  I pulled my cell away from my ear and dumbly stared at it before returning it back to the side of my head.

My mother is single now, widowed for four years, and so am I, divorced for almost the same time.  My two daughters have blossomed into stunning teenagers.  So there you have it: three generations of the female divine navigating through “relationships” infused with testosterone glory, each of us with unique perspectives, experiences, and challenges.  Sandwiched in the middle, I feel self-pressured to provide guidance to all these women in my life, even though I can barely keep it together myself.

“After dinner, I asked him to my condo for a cup of coffee.”  My mother was telling me about her recent date.

My parents were supposed to spend 20 years together enjoying retirement. I was supposed to be happily married.  My daughters were supposed to stay young and innocent forever.  In my wildest dreams, I never imagined we’d end up converging on the same path, all dating at the same time.

I chose my response carefully.   “Some men might mistake an invitation for coffee in your condo as a euphemism for something else.”  The conversation felt awkward and all wrong: me coaching my mother on the nuances and subtexts of dating.

My mother and father had loved each other deeply and genuinely. His brain cancer had plucked my mother from all that was familiar, spun her around, and dropped her into a life dripping with grief and solitude.  She was just beginning to consider companionship with someone other than my father, but it had been over 40 years since she’d been on a date.

“Well, I figured THAT out!  He put the moves on me!”  Her tone revealed astonishment. My mother was youthful, vibrant, and attractive; why wouldn’t he have been interested?  It just wasn’t what she wanted. She had only wanted conversation, so after he had made his move, she had summarily dismissed him.

On the other end of the spectrum, I observe my daughters who know even less about the cues and motives of the opposite sex.  (And let’s be honest, their counterparts don’t understand them either.)  They’ve grown up in a culture where sex is regarded casually, even more so than in my own childhood, and much more than my mother’s.

What are the right words that acknowledge that sex is fun and fulfilling, but comes at the risk of extreme vulnerability?  I want to prepare them by explaining that sex runs the gamut: it can make you feel cherished and adored or cheap and dirty, but sometimes, confused somewhere in the middle.  Is that too blunt?  Or is it too ambiguous? My best advice so far: Take your time.  Don’t rush.  Be selective.

And then there’s me, divorced after an almost 20-year relationship. I’ve discovered that (like myself) men my age have a history.  What takes a little longer to tease out is whether or not they have any baggage.  When I was first dating again, I didn’t always understand the nuance.  Unfortunately, I rushed some things; I’ll summarize by saying I kissed a few frogs.

They’re still frogs.  (Except for one, who’s become my prince, but that’s another story for another time.)

So back to my dating advice for any age:

“3H” Rules of Dating

  1. Preserve Your Headspace.  Never bury who you are, don’t listen to anyone who insists you’re not good enough, and never entertain the notion that you can change or rescue someone.  These are terrible, destructive head games that just aren’t true.
  2. Protect Your Heart. Sadly, your heart will get broken in your lifetime, but you can minimize how often by being cautious. Before you share your heart—widely, fully, and deeply—with someone else, feel certain that they are trustworthy.  Even if you break up, you need to feel confident that they won’t spread your business around town or the internet.  That never helps.
  3. Maintain your Health.  Sexually transmitted diseases are nasty.  Babies are a gift when you’re ready, but a tragedy when you’re not. Use protection to keep yourself safe.

Overall, I think dating is great.  It’s a platform for sifting, sorting, and assessing; it helps you figure out what you DON’T want as much as it helps you figure out what you DO.  Besides, dating is far more entertaining than sitting home alone with Netflix and a glass of wine (or two or three…).

At least, usually.


About Jennifer Hooper

Jennifer Hooper is an old soul. She believes in notions such as intuition and self-trust. She’s a mother to two teenage daughters, and acknowledges that they all have a lot to learn from each other, although all struggle mightily to hear the lessons. Jennifer is passionate about creativity, community vibrancy, entrepreneurship, communication, and raising her daughters to be good people. She also writes at http://www.aneagerlife.com.


  1. That must be weird! Not only are you all dating but you all live closely and can support each other and process it. My mom is a widow also and lives 2 hours a way so the day to day is not the same as it would be if we were closer. It is great that you are building and have built great female to female relationships with your mom and your daughters, rather than competitors you are demonstrating friendship and support. Thanks for the post Jenn – I have a few folks in mind I want to share this with!

    • Jennifer Hooper says:

      Kelly, you make it all sound so beautiful!

      The truth is, it’s messy and weird and awkward! My mom lives 3 hours away now, so we talk more on the phone than we see each other. My daughters could care less about my advice (I struggle between saying too much and not saying enough); I just have to trust that what I say does seep in, even if they would never admit it.

      Sadly, there’s no fairy tale here; just a raw, imperfect family of women doing the best they can to be strong and survive! xoxo

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