How do I put my wild past behind me?

Dear Lisa,

Lisa I just found you recently and I am so happy I did! I listen to your podcast and I always learn something to help me in my dating journey.

I am almost 50 and have never been married and have no children. I have been a very independent free spirit all my life. I would describe myself as a creative expressionist who is constantly curious and always working toward finding balance and grace. I am an art teacher and just started online dating. I have been in love and I have had my share of dating american and international men. I am a hopeless romantic and may have been too excited and at times more masculine in my past dating behavior.

I am ready to get it right and allow my feminine to receive the masculine. I have too many questions yet for now, I’m always worried about how to answer the question as to why I never married and if I should be honest about how much experience I have had dating? I don’t want to lie, but how to get around the fact that many of my past intimate relations are still friends, stay in contact, and, if I allowed, a few would still be my lovers. I am starting a new life in a new state and I am ready to settle down. I want to have a fresh start and be savvy and authentic in choosing a life partner. I don’t want to blow it by scaring a man away with my wild, liberated past.

Please give me your guidance Lovely Lisa!

–Almost 50 ( ♀ Kamloops)


Dear Almost 50,

Thank you so much for your thoughtful complements. I’m glad my work is useful to you!

There are so many amazing parts of transitioning into a fresh start! In this case though, I’m going focus on this idea ‘settling down, and your ‘wild liberated past’. I can hear your voice in my head when I read your email. You are fun, exciting, seductive and pleasing to be around. There’s more to you that that though, it sound like there is a part of you that is curious whether being more ‘balanced, and graceful’ (and calm and committed and less playful?) if you would find love that matched? If being less wild might mean that you get to enjoy a long lasting, deeper connection that nourishes you.

I think every ‘wild woman’ comes to the point where she wants to be fully seen and appreciated by the masculine, just as every subdued woman would like for the wild parts of herself to be seen and appreciated. I can understand how the wildness feels threatening to the tender shoots of a new relationship. It isn’t the wildness though, that is stopping you from getting what you’re looking for, or even keeping it once you find it. It really is the necessary cultivation of a more radiant feminine that you need to add to your wildness. In other words, you don’t need to drop or leave behind your wildness, because if you did, you wouldn’t feel like you!

Let’s get into your questions. Should you be honest about your past? Yes. The question may never come up, but if it does, it’s fine to say that marriage never felt right before, or that you hadn’t met the right person, or that you had some things to do before you committed yourself to one person or even that you don’t know why, but now things are different. Find the truth inside of you and for the right man, that reason will be enough.

With regards to past boyfriends and lovers, it’s really none of anyones business whether those men are still interested in you or not. And even if the man you are with picks up on it, a little bit of competition does the masculine good! Providing the exes are really of no interest to you, the man you chose to be with should be of the opinion that if he’s the one you’re choosing to be with, then there’s nothing to be concerned about. If you meet someone who won’t let it go, or wants you to end friendships, he’s probably not in a healthy frame of mind – be thankful he let you know sooner than later and move on!

The bottom line is that any man worth seeing needs to appreciate you for everything that you bring to the relationship. If what you bring is your amazing, creative, curious present self, a spicy, wild past, past difficulties with ‘settling down’ or challenges with being vulnerable, then he will need to be able to love all of those parts of you. Leaving any of those parts behind, is essentially creating baggage that you drag around behind you. The goal is to ‘transcend and include’ as Ken Wilber would say, or be everything that you were, plus what you have grown to become.

I’d love to answer your questions about deepening into your feminine and hear about this tendency to get excited and thus more masculine in your dating behavior so, feel free to get in touch as the need arises! And of course, reply in the comments if you need any clarification on the above.

– Lisa



Leave a Reply