Dating Lessons


The word summons groans, horrible stories, annoyance, eyerolls, and frustration like none other. But what about joy? What about curiosity? What about fun? What if I told you that you could experience those things as part of your dating journey?

I’ve had three significant periods of dating in my life and they’ve all been very different. Married at 19, my high school dating was a disaster. I had no idea how to flirt with guys I was interested in and fell too hard for the ones that showed interest in me. Dating was driven by religious and parental rules and lots of assumptions and had very little room for me to consider what I actually wanted for my own long-term happiness.

Divorced at 28, I was mostly single again until 33. That period had a whole lotta not dating at all because I was so consumed with simply surviving single mom-ness and figuring out a career and daycare and paying the bills. Throw in a couple of short-lived love-bombing relationships and awkward set-ups and then a hefty dose of an internalized belief that I wasn’t a complete family on my own with my girls and I fell hard for something I thought was a hollywood love story where the man who was “meant to be” my girls’ dad showed up and we would live happily ever after. I was wrong.

This time around has been a whole other ball-game. I moved out of my second marriage a few days after turning 39 and was simultaneously confident I was making the best choice for myself and my family and devastated that the fairy tale I had desperately wanted to believe was true….wasn’t. While I had spent the previous few years learning how to be truly myself, standing up for my value, and falling in love with myself, I had zero idea how to date. And honestly, I wasn’t sure if I was really interested in finding a relationship. I went on several dates to try it out and learned that I enjoyed flirting....and was about a million times better at it at 40 than I was at 15. I learned I enjoyed meeting new people and trying new things. I also learned that, having just left a sexless marriage where I’d been told often how unattractive and unwanted I was, I really enjoyed hearing men tell me I was sexy and beautiful and all the things. That ended up scaring the heck out of me pretty fast and decided I didn’t actually want to be a woman with a long list of one-night stands or fall fast and hard for someone love-bombing me into thinking something was more than it was.

So I sat myself down and made myself some boundaries. I thought about the type of man I wanted to find. I thought about the things that would prevent that kind of man from showing up in my life or prevent me from being available to see him if he did. I thought about how I wanted to behave in relationships and on dates. I thought about how I wanted to balance dating with continuing to create and build the life I love. I journaled and made lists and journaled some more.

And I went on more dates. I decided to embrace curiosity and be open about receiving what The Universe has for me. And I have learned more about who I am and what I want and have witnessed my own healing in ways I didn’t really see coming. Heck, even dating or not dating during covid shutdowns provided its own set of challenges and lessons--masks, restaurant restrictions, lockdowns all added to the fun! And, word to the wise….while bowling is usually a fun date, don’t even bother with it as a first date where you have to wear a mask and can barely hear the other person!! Just take my word for it. Don't.

So… we go! In no particular order, the lessons learned from my Third Time’s a Charm hand at dating!

  1. I am capable of identifying red flags for myself and making choices based on what is real...not what I *wish* was real..

  2. I am capable of ending a relationship that had deal-breaker behaviors I didn’t see at first.

  3. I am capable of deciding how much to share and when to share it--and that it’s okay to decline engaging in the commonplace low-key trauma bonding that seems to be the norm for first date conversations!

  4. I am capable of deciding my own boundaries about when to engage in sex and holding those boundaries...even when it would be easy not to.

  5. I am capable of deciding my own boundaries about engaging with children and other family--his or mine--and holding those boundaries...even when it would be easy not to.

  6. I am capable of being vulnerable in a relationship, of opening my heart to receive love, care, and kindness from someone who freely gives those things.

  7. I am capable of giving healthy love with openness and vulnerability, at the rate I choose.

  8. I am capable of healthy empathy that does not diminish my own perspective and value.

  9. I am capable of sharing my views, opinions, humor, and perspectives and know that it is okay to not be everyone’s flavor.

  10. I am capable of navigating difficult conversations instead of keeping my mouth shut about things that bother me.

  11. I am capable of rewiring my anxiousness about abandonment issues and hypervigilance in order to practice secure attachment and healthy communication.

  12. I am capable of being fully myself and being loved for *all* of the things I am.

  13. I am capable of accepting and embracing that not everything that is meant to be is meant to be forever.

  14. I am capable of letting go and moving forward...even when the ending is sad or heartbreaking and I know that my worth is NOT determined by someone choosing a different path for themself.

Owning my own capabilities, knowing myself, knowing my own values, knowing my own boundaries, and loving myself made all the difference in being able to enjoy dating this time around. I’ve learned that sadness and joy weave together to make this beautiful messy life that I absolutely LOVE living. I do hope that special person comes along soon….and in the meantime? I’ll be busy living the life I love.

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